Vacation Rentals By Owner In Sarasota, FL

Private pool home, located just by the Turtle Beach directly on Siesta Key Island. This 3 bedroom, 3 bath home is perfect for your family vacation. High ceilings, open floor plan with split bedrooms. Kitchen with granite counters and breakfast bar is open to the living room and dining area. High quality modern feel furniture, laundry inside and attached 2 car garage. Large sliding doors can pocket open to nice sitting area around the pool. Master bedroom features sliding doors and walk in closet! Second Guest bedroom also has king size bed and attached bath, third bedroom has two twin size beds and bathroom in the hallway, also used as pool bath.brBeach with deeded beach entrance and 2 great restaurants are only a short stroll away.brWe speak English, Czech, Slovak and Polish.brbrbrKeywords: beach house, beach house with pool, siesta key house, sarasota pool house, private house on turtle beach

Private Pool Home by Turtle Beach on Siesta Key!

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$175.0

Travel Nurse Retreat | 3BR Near Hospitals | MonthlybrbrWelcome to Casa Macadamia — a fully furnished, centrally located Sarasota home designed for traveling nurses, clinicians, and contract professionals seeking a quiet, comfortable, and reliable extended stay.brbrWhether you’re on a 13-week assignment or relocating temporarily, this peaceful retreat offers space to unwind, work remotely, and rest well between shifts.brbrPrime Location for Medical & Clinical AssignmentsbrbrLocated in the quiet Poinsettia Park neighborhood, you’ll enjoy short commutes to:brbr• Sarasota Memorial Hospital – ~10 minutesbr• Doctors Hospital of Sarasota – ~12 minutesbr• Downtown Sarasota medical offices – ~10 minutesbr• I-75 access – easy regional commutebrbrNearby essentials within walking distance:br• Publix supermarketbr• CVS pharmacybr• Einstein Bagelsbr• Local cafés & restaurantsbrbr-Beaches like Siesta Key, Lido Key and other coastal areas are just minutes away for restorative days off.br-Several Parks in the area, along with trails are also only a few minutes away.brbrDesigned for Comfort During Long AssignmentsbrbrThis professionally managed 3-bedroom home provides space, privacy, and reliability for extended stays.brbrIdeal for:br• 1–3 traveling nursesbr• Clinical teams sharing housingbr• Corporate or relocation staysbr• Medical fellows & visiting professionalsbrbrThe home sleeps up to 6 comfortably, though we recommend 2–4 for optimal comfort during longer contracts.brbrSleeping ConfigurationbrbrBedroom 1: King bedbrBedroom 2: Queen bedbrBedroom 3: Queen bed + twin bunkbrbrEach bedroom includes:br• Smart TVbr• Quality linensbr• Window blind coveringsbrbrWork-Friendly Amenitiesbrbr• High-speed Wi-Fibr• Spacious dining table (ideal as workstation)br• Quiet neighborhoodbr• Central ACbr• Washer & dryer in unitbr• Iron & ironing boardbrbrFully Equipped Kitchenbrbr• Stainless steel appliancesbr• Coffee maker (drip + French press + Keurig)br• Blender & toasterbr• Dishwasherbr• All cookware & essentials includedbrbrOutdoor grill and patio seating available for relaxing evenings.brbrHousekeeping & Maintenancebrbr• Professional cleaning prior to arrivalbr• Mid-stay cleaning available for extended contracts (fee applies)br• 24/7 local support via Siesta Getawaysbr• Professionally managed propertybrbrWe prioritize reliability, responsiveness, and clean, well-maintained accommodations.brbrFlexible Extended StaysbrbrThis property complies with Sarasota’s 7-night minimum stay requirement.brbrIdeal contract windows:br• 4–13 weeksbr• Extension options availablebr• Inquire for custom contract lengthbrbrMonthly pricing available upon request.brbrAdditional Detailsbrbr• 3-car drivewaybr• Residential settingbr• Mid-cleaning availablebrbrVacation Rental Certificate: VR24-00180brbrWhy Clinicians Choose Casa Macadamiabrbr✔ Short commute to major hospitalsbr✔ Friendly neighborhood for shift recoverybr✔ Full home privacy (no shared walls)br✔ Fully furnished — move-in readybr✔ Professionally managedbrbrIf you are a traveling healthcare professional seeking dependable, comfortable housing in Sarasota, we invite you to reach out with your assignment dates.brbrWe look forward to hosting you during your time in Sarasota.brbr— Siesta GetawaysbrThank you for choosing Casa Macadamia for your extended stay. These guidelines help maintain a comfortable and respectful environment for both guests and neighbors.brbrRegistered Guests OnlybrAll individuals staying overnight must be listed on the reservation.brNo unregistered overnight guests are permitted.brbrNo Third-Party BookingsbrThe person booking must be the primary guest staying at the property.brbrPrimary Guest VerificationbrThe host reserves the right to verify the identity of the primary guest prior to check-in. A valid government-issued ID may be requested if necessary.brbrOccupancybrMaximum occupancy is as stated in the listing.brIf you require accommodations for additional guests, please inquire prior to booking.brbrPurpose of StaybrThis home is intended for extended professional stays, relocation, and quiet residential use.brParties, group events, celebrations, and disruptive gatherings are not permitted.brMinimum booking age: 25.brbrSelf Check-InbrThis is a self check-in property. Access instructions will be sent prior to arrivalbrbrNo Smoking or VapingbrSmoking or vaping is not permitted anywhere inside the home.brEvidence of indoor smoking will result in an additional cleaning fee.brbrQuiet HoursbrIn accordance with Sarasota noise regulations, quiet hours are from 9:00 PM to 9:00 AM.brPlease be mindful of neighbors at all times.brbrParkingbrDriveway parking for up to 3 vehicles is included.brStreet parking must comply with local regulations.brbrHousekeeping for Extended StaysbrFor stays longer than 14 days, a mid-stay cleaning fee of $120 will apply per cleaning.brAdditional cleanings may be requested.brbrGrill UsebrIf using the outdoor grill, please clean it prior to checkout.brFailure to do so may result in a $125 cleaning charge.brbrRespect for the HomebrPlease do not move furniture and leave furnishings and household items in the home at checkout.brAdditional fees apply only if damages, excessive cleaning, or rule violations occur.

Travel Nurse Retreat | 3BR Near Hospitals | Monthly

Sarasota, Florida, United States

Bed

Bath

Sleeps

$905.37

☀️ Siesta Sun Oasis | Private Pool, Walk to Siesta Key Beach, Game Room & Large Backyard Courtbrbr Why You'll Love This HomebrSiesta Sun Oasis offers a spacious island retreat designed for gathering, relaxing, and enjoying time outdoors. With five bedrooms and a large backyard built for recreation, this home makes it easy to balance beach days with time spent at home. The private pool and oversized concrete court create a setting where everyone can find their favorite way to unwind, from poolside lounging to friendly games of pickleball or soccer. Inside, the home blends comfort and functionality with generous living spaces and a well-equipped kitchen featuring LG appliances, a wine cooler, and a combination microwave, air fryer, and oven for easy meals and entertaining. Siesta Sun Oasis provides the space to enjoy every part of your stay.brbr ‍ ‍ Perfect ForbrFamilies, multi-generational groups, or friends looking for a spacious Siesta Key stay with outdoor activities, poolside relaxation, and room for everyone to spread out.brbr ️ Imagine ThisbrStart the day outside as the morning sun fills the backyard. Plan the day around a quick trip to Siesta Key Beach before returning home to cool off in the private pool. In the afternoon, challenge friends to a game on the backyard court, perfect for pickleball, soccer, or casual outdoor play while others relax by the pool or gather inside around the pool table. As evening settles in, the backyard becomes the heart of the home. Start up the grill, share stories from the day, and enjoy the warm island air before retreating indoors to comfortable bedrooms across the home.brbr Where You'll Sleepbr • Bedroom 1: King Bed, Ensuite Bath, TVbr • Bedroom 2: King Bed, TVbr • Bedroom 3: Queen Bed, TVbr • Bedroom 4: Queen Bed, Ensuite Jack and Jill Bath, TVbr • Bedroom 5: Queen Bed, Ensuite Jack and Jill Bath, TVbr • Office: Sleeper Sofa (Connected to the Primary Suite)brbr Explore the Areabr • 0.5 Miles to Siesta Key Beach – Powdery White Sand and Gulf Swimmingbr • 1.5 Miles to Siesta Key Village – Restaurants, Coffee Shops, and Island Boutiquesbr • 1.6 Miles to Crescent Beach – A Scenic Stretch of Shoreline with Calm Watersbr • 6.0 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Diningbr • 9.2 Miles to St. Armands Circle – Upscale Shopping and Restaurantsbrbr⌛ Book Today: Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome one small dog (up to 25 lbs) with a $250 pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup's stay just as wonderful as yours.

Siesta Sun Oasis | Private Pool, Walk to Siesta Key Beach, Game Room

Sarasota, Florida, United States

Bed

Bath

Sleeps

$293.17

Aloha Kai #42brbrLets Go to the Beach!br brEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #42. This charming beach villa is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Fresh and inviting with colorful coastal comfort, Aloha Kai #42 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special: br brBedding Arrangement: br1 Bedroom: brMaster Suite: King-size bed and Smart TV brAdditional Sleep: Queen-size sleep sofa in the living areabrTop Features: brSleeps 4 brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation. brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort. brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun. brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #42 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this villa offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #42 today and create memories that will last a lifetime! brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future! brDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Condo

Beach Getaway! - Aloha Kai #42 - Roelens

Sarasota, Florida, United States

Bed

Bath

Sleeps

$188.07

Welcome to The Strand, where luxury waterfront living meets convenience and comfort. brThis rental unit features one bedroom, one den and two FULL bathrooms. brbrEnjoy amenities such as a heated outdoor pool, spa, fitness center, kayak launch, two communal barbecues, elevator access, and secure community entry—all just a short drive from downtown Sarasota. brRelax on your balcony overlooking the serene Whitaker Bayou.brbrWe have taken great care to ensure that you have everything you need to feel at home during your stay.brbr★Living Area:brThe living area, located down the hallway, features a cozy full-size pull-out couch, an armchair, a coffee table, and a smart TV for streaming (requires your own login credentials) equipped with Roku for free TV streaming. The space also provides direct access to the balcony through sliding glass doors.brbr★Kitchen:brThe kitchen features brand new appliances such as a stove, oven, microwave, fridge, dishwasher & disposal, toaster, kettle, and coffee machine.brIt has 3 bar stools to enjoy the breakfast bar.brA new sponge, dish soap, trash bags and dishwashing detergent to get you started are included.brbr★Dining:brThe round dining table can comfortably seat 4 guests.brThe breakfast bar seats 3.brbr★Master bedroom:brLocated on the left-hand side upon entering the condo, it includes a Queen-sized bed, a dresser with a smart-tv, a nightstand with lighting as well as access to the en-suite bathroom. Bedding & linens are included.brbr★Den:brConsidered a guest bedroom without a window, it features a twin-sized bed, a desk with a chair, and closet. Bedding & linens are included.brbr★Bathrooms:brThe master bath is connected to the bedroom. It features a large walk-in shower, sink and toilet, and a large dressing room.brWasher and Dryer are located in master bathroom.brThe 2nd bathroom features a bathtub with sink and toilet. brTowels, a blow dryer and essential soap products are included.brbr★Balcony:brThe balcony can be accessed through the large sliding doors in the living room and features 4 chairs and a small side table. brIt is the perfect location to enjoy the sunsets on the bay!brbr★Laundry:brThe washing and dryer machines are located in the master bathroom.brBasic detergents are supplied to start you off.brbr★Parking:brYou have one reserved spot inside the parking garage.brPlenty of uncovered guest parking available on a first-come first-serve basis.brbr★Community amenities:brCommunal pool & Gym, please note that pool temperature may vary depending on outdoor conditions, and during colder weather, it may not always reach the desired setting. The pool is heated seasonally in accordance with Homeowners Association guidelines. Guests are kindly asked to follow all HOA pool rules, including posted hours of operation.brKayak Launchbr2x barbequesbrEV charging stationsbrSecure entrybrbr★Accessories:brBeach towelsbrbr★Miscellaneous:brSelf check-in starting 4 pm & self check-out by 10 am.brSecure community with MyEnvera gate system.brCar charging stations available.brIf you wish to receive mail, it must be sent to our Orquera Florida Investment office - Sarasota downtown.brbr★Location:brDowntown Sarasota – 5-10 min drivebrLido Beach - 15 min drivebrSiesta Key Beach - 25 min drivebrWicked Cantina Mexican Restaurant & Subway within walking distance.brNew Bay Park – 5 min drive/10 min walkbrThe Westin – 5 min drivebrThe Ritz – 5 min drivebrbr★Pet Friendly:br We’re happy to welcome your furry friends! Please note that breed and size restrictions may apply. A $150 non-refundable pet deposit is required.brbr★Important Notes & Rules:br- This rental requires HOA approval, which includes submitting your email address, a copy of your driver’s license, current address, vehicle information, and a $150 fee (included in booking, fee subject to change). To begin the application, please promptly provide your email address. While we will apply on your behalf, we are not responsible for any delays in the process due to late submission of required information.br- For your safety, swimming is at your own risk, and children must be supervised at all times.br- No parties and no smoking on the premises.br- AC temperature should not be set below 70°F, and heating must not exceed 77°F.br- Please ensure doors and windows remain closed when the AC or heating is running.br- The residence is located on the canal without a fence. Children must be supervised at all times.br- If you need elevator assistance, please note that elevators may be temporarily disabled during severe weather. Stairwells are available as an alternative.brbr★Add-on:brTraveling with a little one We offer a Pack 'n Play for use during your stay for a one-time fee of $50. This includes clean, fitted sheets for your convenience. Just let us know in advance if you'd like to add this to your booking!brbr★Wildlife Awareness:brFlorida's diverse wildlife awaits responsibly; refrain from direct contact and adhere to safety guidelines. For more information, visit the Florida Fish and Wildlife Conservation Commission.brbrAre you traveling with family or friends We manage other units in The Strand, just ask us!brbrFind us on FB or IG: Orquera Florida InvestmentsbrbrYour unforgettable getaway awaits!

Condo

NEW! Waterfront Luxury in Sarasota – Near Downtown & Beaches!

Sarasota, Florida, United States

2

Bed

2

Bath

4

Sleeps

$759.52

Nestled in Sarasota, this delightful house offers everything you could imagine. Met by cozy sofa, equipped kitchen, beautiful interior design you will feel like you reached your destination.Few sitting areas outside, heated pool, big windows and lots of room will make you want to stay in Florida for ever. This is a spot. Dream come true. So amazing.

Modern Family home with heated pool

Sarasota, Florida, United States

Bed

Bath

Sleeps

$186.51

Create memories with this surf shack-inspired private apartment with an easy mile walk to the crystal white sands of Siesta Key & just minutes from central Sarasota surrounded by fun things to do. Sleep well in your comfy queen size bed with luxurious bamboo linens. The unit offers a themed living room with a flat-screen TV, fast WiFi, comfortable seating, and a fully equipped kitchen, as well as a private patio just off your unit, leading to the heated pool, shared with one other unit.brbrYour Siesta vacation begins the moment you pull into the private driveway of this retro-inspired mid-century modern tropical villa. Located exactly one mile to Siesta Beach, this mainland location is also close to dining and shopping so you can walk pretty much anywhere! brbrThe apartment provides a surf shack inspired decor offering 1 private bedroom with a super comfy queen-size bed with bamboo linen, along with a pull out sofa in the living room. Featuring a blend of new and retro designed decor, you are inspired to kick off your shoes and leave your worries behind while enjoying your stay. Beachside Bliss offers a designer appointed living room with a flat-screen TV hosting premium streaming channels, Wifi, and comfortable seating. The kitchen is fully equipped with everything you need, from a coffee maker, toaster, and microwave to cutting boards so you can slice fresh limes for your Florida inspired cocktail. brbrOut on the pool deck is a heated pool shared with one other unit. There is also a comfortable, shaded lounge area off your unit that's perfect for enjoying a morning cup of coffee or cool beverage in the evening. Pool toys, and towels are available in the laundry room. We invite you to relax and have fun! br brAnd . . . since Siesta Key's beaches are calling, we've provided toys and rafts, umbrellas, beach towels, and chairs for your use. A shared gas barbecue grill and picnic table invite you to enjoy dining al fresco while relaxing in the Florida lifestyle. If your stay includes a cool night, you can step out to the backyard garden where you can enjoy sitting around the fire pit enjoying s’mores while gazing into the crackling fire. br brIf you’re lucky enough to visit during the mango season, we welcome you to help yourself to as many of these tropical delicacies as you’d like from the giant tree in the backyard. However, they can be tricky to cut, so please look up an on-line tutorial on slicing fresh mangos so you cut them safely.brbrThe ground-level apartment in this villa is completely private. It has its own door lock code which will be provided upon confirmation so you can arrive any time after the 3 pm check-in time. With onsite parking it will be easy moving into and around the villa, so you’re free to enjoy your vacation from the moment you arrive! The unit is furnished with everything you need to enjoy your vacation, with extra linens and beach towels provided.brbrWe are proud of our over 500 five star reviews, but even more thrilled that you’ve chosen to spend your vacation at our villa. We are committed to making sure you enjoy your vacation. br brThe house manual provides information about the shops, dining, and entertainment nearby, but if you're looking for specific advice on dining or age-appropriate activities around the area, just ask.brbrSarasota is our home and we love the area surrounding world-famous Siesta Key. If you need anything, please refer to the contact number provided in your br home manual, at any time day or night. brbrWe want this vacation to be your best vacation and hope you'll enjoy the many advantages of renting a private home over a hotel.brbrWhen heading out for a day or night on the town, there's always somewhere great to explore whether you turn left towards Siesta Key or right, towards Sarasota’s Gulf Gate area. There is so much to do!brbrJust west over the Stickney Point Bridge, you’ll find Daiquiri Deck, Spearfish Grill, Coconuts, and award-winning Capt Curt’s Crab and Oyster Bar. If you’d like a tropical drink fresh off the beach, stop by their outdoor bar - Sniki Tiki. Further south is the Toasted Mango Café (great for breakfast) or if you'd like to cook at the apartment, pick up some fresh fish at Big Water Fish Market. For date night, you can’t go wrong driving towards the southern tip of Siesta Key for romantic bayside dining at Ophelia's on the Bay. If you like French food, stop by Miquel's but save room for one of their tableside desserts!brbrIf you head east from the apartment, you’ll find a number of restaurants in the nearby shopping plaza, including Plaza Mexico, Carrabba’s Italian Grill, and Abel’s Ice Cream. Also within walking distance is Sarasota’s own Gecko’s Grill & Pub (an indoor and outdoor sports bar so guys won’t miss the big game or prizefight) and Ruth Chris Steak House. The best part is you don’t have to cross a major road to get there!brbrIf you want to stock up for a vacation around the pool, there is a Publix Shopping Center nearby, a gluten-free bakery, and two bathing suit stores! Don’t forget the extra sunscreen!brbrAdditional restaurants (too many to mention) as well as an eclectic nightlife can be found less than a mile away in the quirky Gulf Gate Village, known as the culinary “Epcot” of Sarasota. Name a cuisine, and you’ll probably find it in Gulf Gate Village! Just look up Gulf Gate Village online and pick your destination ahead of time. You may need reservations if you’re visiting during our busy tourist season.brEnjoy!brbrIt's easy to get around Sarasota via Uber, Lyft, and public buses. If you're on Siesta there is a free ride taxi service that zips from the beach to Siesta Village – just tip your driver! When parking on Siesta Key, take advantage of the free public parking lot. If parking on one of the side streets, keep an eye on the time limit posted on the parking signs.brbrIt's All About Siesta!brOur villa is less than a mile to Siesta Key where you can choose between three amazing beaches along the sparkling blue waters of the Gulf of Mexico. Siesta Key Beach has been voted the Best Beach in America numerous times for its 99% white quartz sand; famous for its cool, silky texture and healing properties. While each one of Siesta's beaches; Turtle, Crescent, and world-famous Siesta Key Public Beach offers a slightly different experience, they all share the same gorgeous waters, breathtaking sunsets, relaxing gulf breeze and a chance to see playful dolphins, sea turtles, manatees, and even stingrays.brbrIf you're looking for a private beach experience, Turtle Beach (south of the Stickney Point Bridge) and Crescent Beach (just one mile over the bridge to Access 12) will be ideal for you. However, if you're looking for a vibrant, busy beach with lifeguards, beach volleyball, concession stands, and public restrooms, Siesta Key Public Beach is the place to be. Providing free parking, Siesta's Public Beach offers free tennis and volleyball courts as well as a shaded playground, picnic areas, and several concession areas where you can grab a snack and cool drink. Make sure you take a garbage bag with you to pick up after all the fun! brbrIf you're lucky enough to stay over a Sunday night, you won't want to miss the Siesta Drum Circle, which takes place at sunset every Sunday at Siesta Key Public Beach, just south of the sand volleyball courts. What better way to mark the end of an awesome vacation weekend. Siesta Key is an experience you don’t want to miss!brbrIf you're looking for paddleboard, kayak, or bike rentals, you can find great rentals at Siesta Key Bike & Kayak or Ride & Paddle by Siesta Sports Rentals. Jet skis can be rented at Siesta Key Watersports and Siesta Key Jet Ski, while fishing charters and boat rentals are available at Siesta Key Marina. All of these locations are close to a mile from your apartment.brbr✦ HOUSE RULES ✦brbrbrTo help keep the property comfortable for everyone, we kindly ask that you keep the following in mind:brbr• Your reservation includes parking for one vehicle.brbr• Please do not invite additional visitors onto the property without prior permission.brbr• This apartment is part of a duplex, so we ask that noise in the outdoor areas be kept at a respectful level at all times.brbr• You’ll have a fully private apartment, and the shared outdoor pool area, laundry room, and grounds are fully available for your use during your stay.brbr• For safety, please use plastic glasses only in the pool area.brbr• This is a non-smoking property, so we kindly ask that you do not smoke anywhere on the premises.brbr• Please be sure to let us know if there is anything we can do for you during your stay. We want to make your visit as enjoyable as possible.brbr✦ Welcome, and enjoy your stay in beautiful Siesta! ✦

Beachside Bliss- 1 mi to the beach w/ heated pool

Sarasota, Florida, United States

Bed

Bath

Sleeps

$224.99

Leave the world behind at Zen Den, a 1 bed/1 bath apartment only 1.7 miles from the white quartz sands of Siesta Key. The inspiration of nature creates a welcoming aura in this cozy space, with everything you need to enjoy your stay. The open concept living space offers a fully equipped kitchen, dining area, bedroom with queen-size bed and a pull-out sofa for additional sleeping. French doors lead to a pool, hot tub, outdoor lounge, and BBQ area that are shared with the other apartments on the property.brbrEscape the hustle and bustle of everyday life in this artfully appointed 1 bedroom/1 bath apartment inspired by the calming tropical colors and textures of nature. Step through the private entrance into the well-appointed apartment featuring a compact kitchen offering all the accouterments to make a meal at home, from coffee maker to microwave, cookware to cocktail glasses, and cutlery to slice into fresh limes for your Florida inspired cocktail! An open concept living area provides enough space to relax and unwind or unfurl your yoga mat for morning stretching and meditation. Free Wifi is provided, along with flat-screen televisions in the living room, hosting streaming premium channels for your enjoyment. Sleep in the peaceful cocoon of your bedroom, tucked into a quiet corner with a queen bed offering all-natural linens and subdued lighting, ensuring a quiet, restful stay. brbrJust outside the French doors is a sparkling semi-private pool with a covered patio and island-inspired lounge that are shared with only one other unit. The outdoor kitchen with gas grill and dining area with seating for six makes the perfect setting for an evening of dining al fresco. When you're not at Siesta beach or exploring the wonders of Sarasota, you'll enjoy the large sparkling pool with multiple seating areas, ideal for soaking up the Florida sun or tucking under the shaded lounger with a good book or an afternoon siesta. Pool toys and towels are provided for your use, as well as coolers and beach chairs you're welcome to use at the beach. In the evening, you're invited to enjoy the fire pit located in the yard where you can reminisce about your day while gazing into the crackling fire or making S'mores.brbrThis ground level apartment provides convenient onsite parking and access provided via an electronic lockbox, making your vacation accommodations stress free from the moment you arrive! Zen Den has been staged for your comfort, with extra linens and beach towels provided. There is a shared pool area as well as a laundry room just outside your apartment where you can leave wet or sandy towels. Check-in any time after 3 pm. Your unique access code will be provided upon confirmation.br.brWe are committed to making sure you enjoy your vacation. brThe house manual provides information about the shops, dining, and entertainment nearby, but if you're looking for specific advice on dining or age-appropriate activities around the area, just ask. brbrSarasota is our home and we love the area surrounding world-famous Siesta Key.brbr If you need anything, please call the number provided in your home manual, at any time day or night. brbrWe want this vacation to be your best vacation and hope you'll enjoy the many advantages of renting a private home over a hotel.brbrWhen heading out for a day or night on the town, there's always somewhere great to explore just a short distance from Zen Den. On US41/Tamiami Trail, just north of the turnoff to the neighborhood is the Philippi Mansion grounds, where every Wednesday morning during the cooler months the Phillippi Framer's Market offers fresh fruits and vegetables, Amish Donuts, food trucks, local artesian crafts, and foodstuffs. brbrIf you're looking to dine out, there are some highly acclaimed restaurants within walking distance of Zen Den. Sardinia Italian Restaurant and Isan Thai are both open for dinner and so close you drove past them on your way to Zen Den! Also just around the corner is Simon's Coffee House, a great place for breakfast and lunch. Just a short drive further north, on the east side of Tamiami Trail is the Phillippi Creek Restaurant and Oyster Bar, a great spot to enjoy fresh seafood either inside in the air conditioning or outside at one of the picnic tables lining the waterfront of Phillippi Creek. brbrAlso on Tamiami Trail, 1.5 miles north from Zen Den, is the Landings Shopping Center, with a large Publix Grocery Store, a Starbucks, and a number of locally-owned restaurants including DaRuma Japanese Steakhouse and Sushi Bar, OfKors Donuts and Bakery, Apollonia Greek Restaurant, Corkscrew Deli, and several others. brbrIf you head south, just a mile down Tamiami Trail is the Stickney Point Bridge, which takes you to Siesta Key. There you’ll find Daiquiri Deck, Spearfish Grill, Coconuts, and award-winning Capt Curt’s Crab and Oyster Bar. If you’d like a tropical drink fresh off the beach, stop by Capt. Curt's outdoor bar - Sniki Tiki. Further south is the Toasted Mango Café (great for breakfast) or if you'd like to cook at the apartment, pick up some fresh fish at Big Water Fish Market. For date night, you can’t go wrong driving towards the southern tip of Siesta Key for romantic bayside dining at Ophelia's on the Bay. If you like French food, stop by Miguel's but save room for one of their tableside desserts!brbrIf you want to stay on the mainland, less than a mile from Zen Den on the west side of Tamiami Trail is a great new steakhouse called GrillSmith, a scratch restaurant with a varied menu and a full bar. On the east side of Tamiami Trail, you'll find Pietro's Italian Restaurant, where you're sure to be spoiled, Pho 101 Noodle House, and a Dunkin Donuts. brbrThere are also a number of restaurants in the shopping plaza on the southwest corner of Stickney Point. There you'll find restaurants including Plaza Mexico, Carrabba’s Italian Grill, and Abel’s Ice Cream. If you stay on Tamiami Trail past Stickney Point Road you'll find Gecko’s Grill & Pub (an indoor and outdoor sports bar so guys won’t miss the big game) and Ruth Chris Steak House. So there is a little bit of everything within a mile or so from Zen Den. brbrJust enter the name of any of these restaurants into your mobile phone's search and you'll find easy directions to get there. Enjoy!brbrIt's easy to get around Sarasota via Uber, Lyft and public buses. If you're on Siesta there is a free ride taxi service that works on tips to zip you from the beach to Siesta Village. brbrIf parking on Siesta Key, there are a number of free public parking lots, otherwise you'll want to keep an eye on your watch when parking in areas designated for limited parking hours on the side streets.brbrZen Den is 1.7 miles to Siesta Key where you can choose between three amazing beaches along the sparkling blue waters of the Gulf of Mexico. Siesta Key Beach has been voted the Best Beach in America numerous times for its 99% white quartz sand; famous for its cool, silky texture and healing properties. While each one of Siesta's beaches; Turtle, Crescent, and world-famous Siesta Key Public Beach offers a slightly different experience, they all share the same gorgeous waters, breathtaking sunsets, relaxing gulf breeze and a chance to see playful dolphins, sea turtles, manatees, and even stingrays.brbrFor those guests looking for a private, less crowded beach experience, Turtle Beach (4.7 miles south of Stickney Point Bridge on Midnight Pass Road) and Crescent Beach (just 1.7 miles over the bridge to Beach Access 12) will be ideal. However, if you're looking for a vibrant, busy beach with lifeguards, beach volleyball, concession stands, and public restrooms, Siesta Key Public Beach is the place to be. Providing free parking, Siesta's Public Beach offers free tennis and volleyball courts as well as a shaded playground, picnic areas, and several concession areas where you can grab a snack and cool drink. t Siesta's public beach is easy to find . . . just turn right off Stickney Point Bridge and follow Midnight Pass to the public parking lot. Note: Whatever beach you visit, make sure you take a trash bag with you to pick up after all the fun! brbrIf your vacation has you staying over during a Sunday night, you won't want to miss the Siesta Drum Circle, which takes place at sunset every Sunday at Siesta Key Public Beach, just south of the sand volleyball courts. You can join in with the crowds and wander off down the beach a bit and meditate to the sounds of beach drumming. What better way to mark the end of an awesome vacation weekend. Siesta Key is an experience you don’t want to miss!brbrIf you're looking for paddleboard, kayak, or bike rentals, you can find great rentals at Siesta Key Bike & Kayak or Ride & Paddle by Siesta Sports Rentals. Jet skis can be rented at Siesta Key Watersports and Siesta Key Jet Ski, while fishing charters and boat rentals are available at Siesta Key Marina. All of these locations are just over Stickney Point Bridge. brbr✧ HOUSE RULES ✧brbrTo help keep the property comfortable and enjoyable for everyone, please keep the following in mind:brbr• The pool, outdoor kitchen, and lounge area are shared with two other apartments, so we kindly ask that all shared spaces be used respectfully.brbr• Quiet hours begin at 10:00 PM. You’re welcome to swim after that time if you’d like, but please be mindful of your neighbors.brbr• For safety, please do not bring glass onto the pool deck. Plastic drinkware has been provided for your use.brbr• Pets are not allowed in the pool or on the patio.brbr• No smoking is permitted anywhere on the property.brbr✧ Thank you for treating the property with care, and enjoy your stay! ✧

Relax & Recharge- Heated Pool & Hot Tub minutes to Siesta Beach and Downtown

Sarasota, Florida, United States

Bed

Bath

Sleeps

$272.34

Enjoy all the comforts of home in this Beach-inspired 2 bed/1 bath just 1.7 miles from award-winning Siesta Key Beach.brbrThe soothing colors of sea, sky & sand create a cheery welcome in this bright vacation residence, with everything you need for a getaway to the beach. The open concept living space offers a fully equipped kitchen, dining area and 50 inch TV.br brJust outside the kitchen is a sparkling heated pool, comfortable lounge area & outdoor kitchen with gas grill, and hot tunbr& shared laundry.brbrbr✧ HOUSE RULES ✧brbrTo help keep the property comfortable and enjoyable for everyone, please keep the following in mind:brbr• This is a non-smoking property. Smoking is not permitted anywhere on the premises.brbr• If you choose to swim after 9:00 PM, please do so quietly and respectfully.brbr• You will have a fully private apartment. However, the outside grounds, including the shared laundry room, heated pool, patio, gazebo, and hot tub, are shared with the other apartments on the property.brbr• Please do not invite outside guests to use the amenities without prior permission.brbr• Pets are not allowed in the pool or on the patio.brbr• We look forward to hosting you in paradise and hope you truly enjoy your stay.brbr✧ Thank you for treating the property with care! ✧

Perfect Location close to Beach & Downtown, Heated Pool, Hot Tub & Pet Friendly

Sarasota, Florida, United States

Bed

Bath

Sleeps

$343.85

Enjoy a peaceful and private stay at our home in the highly sought after Meadows Community of Sarasota. Relax by the pool on the screened in lanai, and dip into the hot tub at night. The home boasts 3 bedrooms, a newly remodeled kitchen, and gorgeous living space. Just 10 minutes from beautiful downtown Sarasota and Lido beach, and 20 minutes from world famous Siesta Key Beach. Enjoy your stay by the pool, or adventure out on the town and dine at one of the wonderful restaurants Sarasota has to offer. Shop till you drop at St. Armond's circle, check out marine life at the Mote Aquarium, take your littles to the Jungle Gardens, and plenty more!brbrWish to stay home and relax Walk along the pathway to the Meadow's sports bar, breakfast/lunch restaurant, and Italian restaurant. The home has a plethora of bikes to chose from to take wherever you desire for an exciting trip.

Peaceful Private Get Away - 10 Minutes from Major beaches!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$275.71

Only 1 mile from the crystal white sands of Siesta Beach, stretch out and have fun in this midcentury modern tropic-inspired private villa w/gorgeous heated pool (shared with another 1 bedroom apt) & outdoor lounge with two firepits. Comfortable King and queen size beds + 2 hotel roll away beds. Living room is an island oasis with a flat-screen TV, great WiFi, and cozy seating. Kitchen is fully appointed w/everything you need, right down to the barware needed for an icy cold cocktail.brbrSarasota is famous for its mid-century modern architecture and Island Paradise of Siesta is your chance to vacation in one of those treasures. Your vacation begins the moment you coast into the private driveway of this retro-inspired tropical villa located exactly one mile to Siesta Beach! This mainland location is so close to dining and shopping you can break out the flip flops and pretty much walk anywhere! brbrYour villa apartment is presented with island oasis decor and a fresh, tropical color scheme. One step in the door and you know you're finally in Florida! Featuring a blend of new and retro designer decor, Island Paradise villa offers a sun-filled living room with a flat-screen TV hosting premium streaming channels, Wifi, and comfortable seating. brbr brThe kitchen is fully equipped with pretty much everything you could need to dine at home, from a coffee maker, toaster, and microwave to cutlery and cutting boards, so you can slice fresh fruit for your Florida, inspired cocktail. Just off the kitchen is a shared laundry room for those wet towels from the beach or pool!br brSpeaking of which, you’ll enjoy relaxing around the shared outside grounds which feature a heated swimming pool, with enough open-air for sunbathing on one of our lounge chairs, with an additional shaded lounge that invites you to relax with a favorite book or an afternoon siesta. Pool toys and rafts, umbrellas, beach towels, and chairs are provided for your use. A gas barbecue grill and picnic table, along with an island-inspired outdoor lounge invite you to enjoy dining al fresco while relaxing in the Florida lifestyle. If your stay includes a cool night, you can step out to the backyard garden where you can enjoy sitting around the fire pit enjoying s’mores while gazing into the crackling fire. br brIf you’re lucky enough to visit during the mango season, we welcome you to help yourself to as many of these tropical delicacies as you’d like from the giant tree in the backyard. Check the internet for instructions on how to slice and peel a mango!brbrThis ground level villa is completely private, with easy access via a combination door lock code which will be provided upon confirmation. So don't worry if you arrive late in the day! Your access code works any time after the 3 pm check-in. With onsite parking it will be easy moving into and around the villa, so you’re free to enjoy your vacation from the moment you arrive! Your access code is provided upon confirmation of your reservation.brbrWe are proud of our over 1000 five star reviews, but even more thrilled that you’ve chosen to spend your vacation at our Island Paradise villa. Our house manual provides information about the shops, dining, and entertainment nearby, but if you're looking for specific advice on dining or age-appropriate activities around the area, just ask. Sarasota is our home and we love the area surrounding world-famous Siesta Key. If you need anything, please call the number provided in your home manual, any time day or night. brbrWe want this vacation to be your best vacation and hope you'll enjoy the many advantages of renting a private home over a hotel.brbrWhen heading out for a day or night on the town, there's always somewhere great to explore whether you turn left towards Siesta Key or right, towards Sarasota’s Gulf Gate area. There is so much to do!brbrJust west over the Stickney Point Bridge, you’ll find Daiquiri Deck, Spearfish Grill, Coconuts and award-winning Capt Curt’s Crab and Oyster Bar. If you’d like a tropical drink fresh off the beach, stop by their outdoor bar - Sniki Tiki. Further south is the Toasted Mango Café (great for breakfast) or if you'd like to cook at the apartment, pick up some fresh fish at Big Water Fish Market. For date night, you can’t go wrong driving towards the southern tip of Siesta Key for romantic bayside dining at Ophelia's on the Bay. If you like French food, stop by Miquel's but save room for one of their tableside desserts!brbrIf you head east from the apartment, you’ll find a number of restaurants in the nearby shopping plaza, including Plaza Mexico, Carrabba’s Italian Grill, and Abel’s Ice Cream. brbrbrIf you want to stock up for a vacation around the pool, there is a Publix Shopping Center nearby, a gluten-free bakery, and two bathing suit stores! Don’t forget the extra sunscreen!brbrEnjoy!brbrSarasota is easy to get around. if you don't want to drive, Uber or Lyft will pick you up at your door, or you can take advantage of SCAT, Sarasota's public buses. If you're on Siesta, there are several free-ride taxi services - just tip the driver! When on Siesta, there are a number of free public parking lots, however, if you park on one of the side streets in Siesta Village, watch for parking signs and keep track of the time limits.brbrIt's All About Siesta!brOur villa is less than a mile to Siesta Key where you can choose between three amazing beaches along the sparkling blue waters of the Gulf of Mexico. Siesta Key Beach has been voted the Best Beach in America numerous times for its 99% white quartz sand; famous for its cool, silky texture and healing properties. While each one of Siesta's beaches; Turtle, Crescent, and world-famous Siesta Key Public Beach offers a slightly different experience, they all share the same gorgeous waters, breathtaking sunsets, relaxing gulf breeze and a chance to see playful dolphins, sea turtles, manatees, and even stingrays.brbrIf you're looking for a private beach experience, Turtle Beach (south of the Stickney Point Bridge) and Crescent Beach (just one mile over the bridge to Access 12) will be ideal for you. However, if you're looking for a vibrant, busy beach with lifeguards, beach volleyball, concession stands, and public restrooms, Siesta Key Public Beach is the place to be. Providing free parking, Siesta's Public Beach offers free tennis and volleyball courts as well as a shaded playground, picnic areas, and several concession areas where you can grab a snack and cool drink. Make sure you take a garbage bag with you to pick up after all the fun! brbrIf you're lucky enough to stay over a Sunday night, you won't want to miss the Siesta Drum Circle, which takes place at sunset every Sunday at Siesta Key Public Beach, just south of the sand volleyball courts. What better way to mark the end of an awesome vacation weekend. Siesta Key is an experience you don’t want to miss!brbrIf you're looking for paddleboard, kayak, or bike rentals, you can find great rentals at Siesta Key Bike & Kayak or Ride & Paddle by Siesta Sports Rentals. Jet skis can be rented at Siesta Key Watersports and Siesta Key Jet Ski, while fishing charters and boat rentals are available at Siesta Key Marina. All of these locations are close to a mile from your apartment.brbr✧ HOUSE RULES ✧brbrTo help keep the property comfortable for everyone, please keep the following in mind:brbr• Please ask for approval before inviting additional guests onto the property.brbr• You will have a fully private apartment. However, the outside grounds, including the shared laundry room, heated pool, patio, gazebo, and hot tub, are shared with the other apartments on the property.brbr• Please keep noise to a minimum after 9:00 PM. We do use a noise monitor to help ensure quiet hours are respected.brbr• This is a non-smoking property. Smoking is not permitted anywhere on the premises.brbr• For safety, no glass is allowed in the pool area. We have provided plastic drinkware for your use.brbr• Most important of all, have fun and enjoy your stay!brbr✧ Thank you for treating the property with care, and enjoy your visit! ✧

Island House -w/ heated pool 1 mi to Siesta beach!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$1940.37

Casa Flamingo – Your Private Waterfront Resort on Siesta KeybrWelcome to Casa Flamingo, a luxurious retreat nestled on nearly an acre of tropical paradise at the coveted north end of Siesta Key. This centrally-located estate offers an unparalleled vacation experience.brExperience the perfect blend of privacy, luxury, comfort, and adventure at Casa Flamingo. Whether you're seeking a tranquil escape or an active getaway, this estate offers the ideal setting for your next vacation, complete with 6-passenger golf cart, 4 kayaks and 2 paddle boards for your recreational enjoyment. brFrom the moment you arrive at Casa Flamingo, you know you’ve entered somewhere special. It's starts with your drive through the gated tunnel beneath the guest house, and you’re welcomed by a royal palm-lined driveway leading to an elegant iron and glass front door framed in a hand-carved stone entrance. Step inside, and you’ll be greeted by the breathtaking centerpiece of the estate—a sparkling blue indoor/outdoor pool lined by graceful stone columns, surrounded with covered living areas. You will wonder if you are indoors or outdoors as you look up to the sky from the pool, or straight ahead to the arch framing the seamless opening to the outdoor, semi-circle, infinity edged portion of this enormous, inviting pool. From the outside you will enjoy the extensive stone tile patio, surrounding by lush tropical landscaping. Follow the path that leads the dock and beach entry for launching the kayaks and paddle boards.brThis thoughtfully designed oasis offers something for everyone. Whether members of your group love basking in the Florida sun, while other enjoy relaxing in the shaded comfort of the expansive covered courtyard, this space makes it easy to enjoy vacation your way—while still being together. Open the multiple, big iron and glass doors to let the breeze drift in, or close them for a more private experience. With features like a pool table, dry bar, and outdoor kitchen, the poolside courtyard is perfect for both connection and relaxation. Indoor luxury and outdoor beauty come together in perfect harmony.brProperty Highlights:br• Indoor/Outdoor Pool Oasis: The centerpiece of Casa Flamingo is its stunning indoor/outdoor pool area, seamlessly blending the comforts of indoor living with the beauty of the outdoors. Surrounded by lush landscaping, it's the perfect spot to relax or entertain.br• Spacious Accommodations: With 6 bedrooms, 7 beds and 6.5 bathrooms, scattered throughout, the estate comfortably accommodates up to 14 guests (maximum of 10 adults). The property includes a main house and a private detached guest house, offering both communal spaces and private retreats.br• Outdoor Entertainment: Enjoy the expansive 3,000 sq. ft. patio, complete with an outdoor kitchen and BBQ grill. The beautifully landscaped acre provide space for outdoor activities, such as Corn Hole and Frisbe Golf. br• Exclusive Amenities: Guests have access to a range of recreational equipment, including 4 pedal kayaks, 2 paddle boards, and a 6-passenger golf cart. brNOTE: The private boat dock is perfect for fishing. A liability waiver is required to bring a boat, or to use the provided recreational equipment. br• Luxury Interiors: Each room is thoughtfully designed with upscale furnishings and tasteful décor, creating a luxury, yet comfortable atmosphere.br• Prime location: Centrally-located minutes from Siesta Key Village, SK Beach, Downtown Sarasota, St Armands Circle, Lido Beach and so much more. Drive the street-legal golf cart anywhere on Siesta Key. br• Privacy and Security: The property features a private gated entrance, along with Ring cameras in at front and back entrances. brThere is no property that even comes close to creating the experience this very unique and special home was created to provide. brWe are ready to welcome you and your guests!brbrCity of Sarasota VR22-00127

Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Sarasota, Florida, United States

7

Bed

6

Bath

14

Sleeps

$225.77

Summary:brbrThis unique combination of three homes offers a total of 3 bedrooms, is in a prime location, and has EVERYTHING you need for an amazing vacation in Sarasota, FL!brbrbrbr• Shared Outdoor Patiobrbr• Fire Pitbrbr• Hammockbrbr• Dedicated Workspacebrbr• Fully Stocked Kitchenbrbr• Drip & Keurig Coffee Makerbrbr• Plush Bedsbrbr• High Speed WIFIbrbr• Family Friendly-High Chair & Pack ’n Playbrbr• Dog Friendlybrbr• Street ParkingbrbrbrbrThe Space:brbrWelcome to Pineapple Paradise #1–3, a unique Sarasota retreat comprising three private homes combined into one stay, perfectly designed for groups seeking space, privacy, and a prime location.brbrbrbrThis thoughtfully arranged getaway offers a total of 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests—ideal for families, friends, or couples traveling together who appreciate having separate spaces under one booking.brbrbrbrLocated in the heart of downtown Sarasota, you’re just minutes from world-class beaches, vibrant dining, shopping, arts, and nightlife. Whether you’re heading to Lido Beach, exploring St. Armands Circle, or enjoying Sarasota’s cultural scene, Pineapple Paradise places you close to it all while providing a relaxed home base to unwind.brbrbrbrEnjoy the flexibility of multiple living spaces, the convenience of a central location, and the charm of a one-of-a-kind setup. This is your perfect Florida escape!brbrbrbrMAIN SPACES OF THE HOME:brbrbrbr– 3 BEDROOMS & 3 BATHROOMS –brbrbrbrPineapple Paradise #1 brbrBEDROOM 1:brbr* Full-sized Bedbrbr* Nightstand and Lampsbrbr* MirrorbrbrbrbrPineapple Paradise #2brbrBEDROOM 2:brbr* Full-sized Bedbrbr* Nightstand and Lampsbrbr* Mirrorbrbr* Ensuite BathroombrbrbrbrPineapple Paradise #3 brbrBEDROOM 3:brbr* Full-sized Bedbrbr* Nightstand and Lampsbrbr* Mirrorbrbr* Ensuite Bathroombrbrbrbr– 3 BATHROOMS –brbr* Full Bathroom with Walk-in Showerbrbr* Ensuite Bathroom with Walk-in Showerbrbr* Ensuite Bathroom with Walk-in Showerbrbrbrbr– CHEF’S KITCHEN –brbr* Fully Stockedbrbr* High-end Appliancesbrbr* Large Refrigeratorbrbr* Ample Cabinetrybrbr* Coffee Maker: Drip & Keurigbrbrbrbr– LIVING ROOM –brbr* Smart TVbrbr* Plush Sofa + Seatingbrbr* Dedicated Workspacebrbr* Open Floor Planbrbr* Queen Size Sleeper Sofa (Pineapple Paradise #3)brbrbrbrGuest Access:brbrThe guest has access to the entire home minus the locked cleaners' closet.brbrbrbrThe Neighborhood:brbrNearby Attractions:brbrMarie Selby Botanical Gardens – ~2 miles away. A lush 15-acre riverside oasis of orchids, bromeliads, koi ponds, and butterfly gardens.brbrbrbrJohn and Mable Ringling Museum of Art – ~1.5 miles. Florida’s official state art museum, offering European, American, and Asian artworks, the Circus Museum, and the Ca’ d’Zan Mansion.brbrbrbrBayfront Park / Downtown Sarasota – ~0.5 miles. Perfect for strolls, kayaking, or grabbing coffee in the heart of the city.brbrbrbrSt. Armands Circle – ~2 miles. A vibrant shopping and dining district full of boutiques, galleries, and eateries.brbrbrbrSiesta Key Beach – ~3.6 miles. Famous for its powdery white quartz sand that stays cool underfoot—perfect for beach lounging.brbrbrbrRestaurants:brbrDry Dock Waterfront Grill – ~0.5 miles. A casual spot offering seafood with a waterfront view—ideal for sunset dinners.brbrbrbrFork & Hen – ~0.3 miles. Cozy, casual comfort food just around the corner—great for relaxed breakfasts or lunches.brbrbrbrOwens Fish Camp – ~1 mile. A beloved local seafood grill with Floridian flair—“grilling fresh every day.”brbrbrbrDrift Kitchen & Bar – ~1 mile. Contemporary coastal cuisine in a chic setting—perfect for intimate evenings.brbrbrbrCafé on St. Armands – ~2 miles. A convenient café for breakfast or lunch while exploring boutiques at St. Armands Circle.brbrbrbrGetting Around:brbrBy Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area.brbrRideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you'll be on your way to your destination in no time.brbrbrbrOther Things to Note:brbrCheck-in is at 4pmbrbrCheck-out is at 10ambrbrbrbr- 1 dog is allowed for $125 per stay, no cats please. We kindly ask that your dog be trained and that you pick up after your dog.brbr- No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors.brbr- Parking in the street for 3 cars. Street parking allowed: yesbrbr- If you're interested in a long-term stay, please reach out to inquire about availability.brbr- Guests must be 25 years or older to book this property.brbr- Please note that the backyard is a shared space, so other guests may also be enjoying the area during your stay.brbrbrbrGUEST VERIFICATION:brbrTo ensure a smooth and secure stay, we require the primary guest listed on the reservation to complete a simple screening process within 48 hours of booking confirmation. Please note that your reservation is not confirmed until these steps are completed.brbrbrbrOnce verified, and prior to check-in, guests will be asked to sign a Rental Agreement that includes:brbr- Agreeing to our rental terms and conditions.brbr- Providing a valid government-issued ID and a matching credit card before check-in.brbr- Paying a non-refundable $60 damage waiver. The damage waiver provides coverage for accidental damage during your stay, as long as it is reported prior to your check-out. This is collected either at the time of payment through the booking platform or afterward, depending on which platform you use to book.brbrbrbrThe damage waiver covers accidental damage that may occur during your stay. To ensure coverage, all damage must be reported promptly while you’re still at the property. We understand there is normal wear and tear at houses but should anything accidentally break or get stained during your stay please just let us know. Thank you!

Pineapple Paradise - 13 min to Beach - Fire Pit

Sarasota, Florida, United States

Bed

Bath

8

Sleeps

$249.3

Summary:brbrEscape to sunny Sarasota with this one-of-a-kind 2-unit retreat, perfect for families, friends, or multi-generational travelers! Rent both 2-bedroom units for extra space, enjoy flexible accommodations, and experience the ultimate vacation filled with relaxation, fun, and memorable moments together.brbrbrbr• Shared Outdoor Patiobrbr• Fire Pitbrbr• Hammockbrbr• Dedicated Workspacebrbr• Fully Stocked Kitchenbrbr• Drip & Keurig Coffee Makerbrbr• Plush Bedsbrbr• High Speed WIFIbrbr• Family Friendly - High Chair & Pack ’n Playbrbr• Dog Friendlybrbr• Street Parking - 2 carsbrbrbrbrThe Space:brbrWelcome to Pineapple 1 & 2, a charming combo listing in the heart of Sarasota—ideal for couples, friends, or a small family traveling together while still enjoying a bit of privacy. This thoughtfully designed retreat offers 2 bedrooms and 2 full bathrooms, comfortably accommodating up to 4 guests. Each unit features a cozy coastal vibe and all the essentials for a relaxing, effortless stay.brbrbrbrLocated just minutes from downtown Sarasota, you’ll be close to beautiful Gulf beaches, top dining spots, shopping, and the area’s vibrant arts and culture scene. Whether you’re soaking up the sun, exploring the city, or unwinding after a beach day, Pineapple 1 & 2 is the perfect home base. Experience the best of Sarasota—comfort, convenience, and coastal charm all in one place!brbrbrbrMAIN SPACES OF THE HOME:brbrbrbr– 2 BEDROOMS & 2 BATHROOMS –brbrbrbrBEDROOM 1 (Pineapple 1):brbr* Full-sized Bedbrbr* Nightstand and Lampsbrbr* MirrorbrbrbrbrBEDROOM 2 (Pineapple 2):brbr* Full-sized Bedbrbr* Nightstand and Lampsbrbr* Mirrorbrbr* Ensuite Bathroombrbrbrbr– 2 BATHROOMS –brbr* Full Bathroom with Walk-in Shower (Pineapple 1)brbr* Ensuite Bathroom with Walk-in Shower (Pineapple 2)brbrbrbr– CHEF’S KITCHEN –brbr* Fully Stockedbrbr* High-end Appliancesbrbr* Large Refrigeratorbrbr* Ample Cabinetrybrbr* Coffee Maker: Drip & Keurigbrbrbrbr– LIVING ROOM –brbr* Smart TVbrbr* Plush Sofa + Seatingbrbr* Dedicated Workspacebrbr* Open Floor PlanbrbrbrbrGuest Access:brbrThe guest has access to the entire home minus the locked cleaners' closet.brbrbrbrThe Neighborhood:brbrNearby Attractions:brbr• Marie Selby Botanical Gardens – A lush 15-acre riverside oasis of orchids, bromeliads, koi ponds, and butterfly gardens.brbr• John and Mable Ringling Museum of Art – ~1.5 miles. Florida’s official state art museum, offering European, American, and Asian artworks, the Circus Museum, and the Ca’ d’Zan Mansion.brbr• Bayfront Park / Downtown Sarasota – Perfect for strolls, kayaking, or grabbing coffee in the heart of the city.brbr• St. Armands Circle – A vibrant shopping and dining district full of boutiques, galleries, and eateries.brbr• Siesta Key Beach – Famous for its powdery white quartz sand that stays cool underfoot—perfect for beach lounging.brbrbrbrRestaurants:brbr• Dry Dock Waterfront Grill – A casual spot offering seafood with a waterfront view—ideal for sunset dinners.brbr• Fork & Hen – Cozy, casual comfort food just around the corner—great for relaxed breakfasts or lunches.brbr• Owens Fish Camp – A beloved local seafood grill with Floridian flair—“grilling fresh every day.”brbr• Drift Kitchen & Bar – Contemporary coastal cuisine in a chic setting—perfect for intimate evenings.brbr• Café on St. Armands – A convenient café for breakfast or lunch while exploring boutiques at St. Armands Circle.brbrbrbrGetting Around:brbrBy Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area.brbrRideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you'll be on your way to your destination in no time.brbrbrbrOther Things to Note:brbrCheck-in is at 4pmbrbrCheck-out is at 10ambrbrbrbr- 1 dog is allowed for $125 per stay, no cats please. We kindly ask that your dog be trained and that you pick up after your dog.brbr- No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors.brbr- Parking is available for 2 vehicles in the street. brbr- If you're interested in a long-term stay, please reach out to inquire about availability.brbr- Guests must be 25 years or older to book this property.brbr- Please note that the backyard is a shared space, so other guests may also be enjoying the area during your stay.brbrbrbrGUEST VERIFICATION:brbrTo ensure a smooth and secure stay, we require the primary guest listed on the reservation to complete a simple screening process within 48 hours of booking confirmation. Please note that your reservation is not confirmed until these steps are completed.brbrbrbrOnce verified, and prior to check-in, guests will be asked to sign a Rental Agreement that includes:brbr- Agreeing to our rental terms and conditions.brbr- Providing a valid government-issued ID and a matching credit card before check-in.brbr- Paying a non-refundable $60 damage waiver. The damage waiver provides coverage for accidental damage during your stay, as long as it is reported prior to your check-out. This is collected either at the time of payment through the booking platform or afterward, depending on which platform you use to book.brbrbrbrThe damage waiver covers accidental damage that may occur during your stay. To ensure coverage, all damage must be reported promptly while you’re still at the property. We understand there is normal wear and tear at houses but should anything accidentally break or get stained during your stay please just let us know. Thank you!

Pineapple Paradise - 2 Units - 13 min to Beach

Sarasota, Florida, United States

Bed

Bath

Sleeps

$174.8

Forget your worries and cold in this spacious immaculate and serene place, surrounded by nature. Located in a dead-end street with a big fenced yard.brCharming 3 bedroom/2 full baths house, minutes away from pristine beaches of Lido Key and Siesta Key (rated #1beach in the nation). Very Close to beautiful and vibrant downtown Sarasota an Saint Armands.br5 minutes away from worl-class performing and art galleries such as the Van Wezel Performing Arts Hall and the Ringling Museum of Art.br5 starts, guest favorite at abnbbr

Close to beaches and downtown, Quiet, Impeccable home

Sarasota, Florida, United States

Bed

Bath

Sleeps

$234.55

NAMED #1 BEST VACATION RENTAL WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE MAGAZINE FOR 2022. br This is a nicely remodeled 650 square foot one bedroom apartment in a historic home located in the coveted safe Northwest Sarasota neighborhood. Outside is your small but quaint front porch. Your front door leads directly into a funky well equipped ovenless galley kitchenette with mini-fridge / freezer. Beyond there you will enjoy tropical-chic decor, original artwork, quality furnishings, petite chandelier over comfy king bed and clean vintage En-Suite bathroom. OUT BACK IS YOUR PRIVATE LANAI, HEATED POOL and OUTDOOR SHOWER. All CLOTHING OPTIONAL. Totally private and not shared with anyone. brThe vibe in this apartment will either relax or entice you. Alternative lifestyle friendly allows you the freedom to totally be yourself away from your home town. Create some new memories. A short one block stroll will reward you with awesome sunsets at our tiny waterfront park where local neighbors and college students gather at sunset. You will have 24 hour access to your villa apartment. You will have access to Florida beach chairs free to use. Northwest Sarasota is safe and friendly and truly Old Florida. The vegetation is old growth and awesome. Very tropical. Houses are an eclectic mix of modern to over 100 years old and modest to mansion. There are three colleges in the neighborhood, a word class museum, micro-brew pub, and Starbucks is in walking distance. Downtown Main Street is 1.5 miles for excellent restaurants, shopping and night life without fighting traffic. Sarasota is mainly a car reliant city. However, the public bus stop is a two block walk. Taxis and Uber are readily available. SRQ airport is a ten minute drive.brbrThe sugar white sands of Lido Beach (my favorite) is a short 10 minute drive. World famous Siesta beach is a 20 minute drive. 1 block walk to Sarasota Bay.

ROYS PLACE Romantic / Private Near Downtown and Beaches. Private Heated Pool!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$180.25

Enjoy the entire 2-bedroom, 1-bath home filled with vintage charm and thoughtful modern updates. Relax in cozy bedrooms, take advantage of a dedicated work space, and enjoy free Wi-Fi and TV.brbrUnwind on the patio by your private pool and tiki bar, perfect for gathering with friends and family. Centrally located just 6 miles from world-famous Siesta Beach and 6.5 miles from Downtown Sarasota and its attractions, this home is ideal for exploring the area — then coming back to a peaceful, relaxing evening.brbrPet-friendly, too

Private Heated Pool 2BD/1BA Just 6 Miles to Siesta

Sarasota, Florida, United States

Bed

Bath

Sleeps

$289.49

Best price for Gulf Front property, on ground floor walk directly out to beach front with spectacular view of Gulf and Siesta Key Sunsets. This unit is 100% renovated with everything new. You will love it!brbrSiesta Key Sunset Family Rentals is family-owned and proud to offer our beach-front Siesta Key (Sarasota) vacation rentals. As a family business, we take great personal pride in ensuring that our condos meet your standards of quality and cleanliness, and we are but a phone call away if you aren't satisfied with anything. brbrSiesta Key has 3 main beaches: Siesta Beach (white powdery sand), Turtle Beach (quieter area/less people/traffic, a great shelling beach) and Crescent Beach (snorkeling/fishing area). brbrSiesta Key Sunset Family Rentals are located at the Fisherman’s Cove Condominium directly next to Turtle Beach on the southern end of Siesta Key, right next to Casey Key. It is not crowded and more of an Old Florida environment.brAll units are direct Gulf Front property no more than a 15 feet walk to and facing the Beach from the lanai to enjoy Siesta Key’s beautiful sunsets, thus our name. We have three ground floor units for easy walk out to the beach and one 3rd floor with elevator for those who prefer an upper view. You will fall asleep each night to the sound of the waves.brbrOn the other side is the parking and Fisherman’s Cove Lagoon with boat docks for those who bring their own boats, (boat trailers are not allowed on premises but we can find you off lot parking) fishing piers, fish cleaning station, BBQ grills. You are literally surrounded by water! Fisherman’s Cove Lagoon leads out to Roberts Bay and the Intercostal waterway.brbrAlthough it is a 10-minute walk to local grills and fine restaurants, this area is quieter and less congested than Siesta Beach and Siesta Village which is only 4 miles away. For those who don’t want to drive, they can take the free Siesta Key Breeze Trolly around the island. For details see:brSiesta Key Association Have questions about the Siesta Key Breeze Trolley - Siesta Key AssociationbrbrEach unit is tastefully furnished and fully equipped with all your kitchen appliances and utensils needs. There is a washer dryer in each unit along with fast wireless internet and cable tv. br brFor outdoor activities each unit has beach chairs, towels, children’s play toys, an umbrella, in addition to limited fishing gear. Shared with 3 other units on a first come first available basis is a canoe, several Kayaks and Paddleboards. Upon request we also have available a pack-n-play and highchair. You do not have to bring anything but your vacation attitude.brbrFisherman's Cove Condominium provides a library, meeting room, shuffleboard court and heated pool. brbrAll units are two bedrooms (king bed in master, 2 twins in 2nd bedroom. , 2-bath, and Sleeper Couch.brbrGuests are responsible for obtaining vacation Insurance at their own discretion.brWe only give refunds if the condominium is not suitable for occupancy, i.e., no water or electricity for an extended period. If an event occurs while guest has arrived, then the refund will be prorated per night.brWe do not give refunds for medical issues, inclement weather, hurricanes, or red tide. Again, we advise getting vacation insurance.brbrHere is an example of the type of reviews we receive.brbrEnjoyed Very Much. Highly recommend!brI came down with my daughter and three little granddaughters. I communicate with the owner a few times before the trip, and they were very quick at replying back. They were the only owners in this complex that worked with us so we could stay from Monday to Monday. We stayed in unit B102. The unit was clean and had everything we needed and more. The girls loved the beach toys and my daughter, and I enjoyed the beach chairs. The first day we saw dolphins in the ocean out the back door and manatees in the bay out the front door, one morning we were at the beach and a manatee swam right by us. We also enjoyed the kayaks, we took 3 of them out through the mangrove trees and stopped at the beach and saw a biologist with some baby sea turtles, it was a great experience for my granddaughters who are home schooled. We enjoyed our trip tremendously and will be back. Thank you very much for sharing your beautiful place with us.brbrWe'd love to serve you and will do our very best to ensure a great vacation stay. We know that our renters may get one vacation a year and hope to make it as promised and stress free.brbrSincerely,

Condo

Fisherman's Cove Gulf Front totally renovated and new furnishings

Sarasota, Florida, United States

Bed

Bath

Sleeps

$407.47