Vacation Home Rentals By Owner In Sarasota, FL

Family-Friendly Home Near Siesta Key & Downtown SarasotabrbrWelcome to your home away from home! This beautiful and spacious house is perfect for families or small groups, comfortably sleeping up to 6 guests:brbr Bedroom 1 – King-size bedbr Bedroom 2 – Queen-size bedbr Additional sleeping – Two foldable twin-size bedsbrbrEnjoy your own private heated pool, automatically maintained at a comfortable 85°F daily — perfect for morning swims or relaxing evenings under the stars.brbrWe also provide beach towels, an umbrella, 4 beach chairs, and a beach cooler so you're fully prepared for your Siesta Key adventures.brbr Located in a quiet neighborhood just:br10–15 minutes from Siesta Key Beach – ranked the #1 beach in the U.S.br10 minutes from Downtown Sarasota – full of restaurants, shops, arts, and local culturebrAt the property, you’ll find a welcome book with all necessary information for your stay — how to contact the host, places to visit, and more.brWasher and dryer are also available for your convenience.brbrFor your peace of mind, a Ring doorbell camera is installed at the front entrance.brbrThis is the perfect spot for beach getaways, city adventures, or simply relaxing poolside with loved ones. A fantastic home base offering comfort, convenience, and all the essentials for your Sarasota stay.brbrHouse Rulesbrbr-No smoking inside the house.br-Pets allowed with a $150 fee per pet (max 30 lbs). Please notify us before booking.br-Unauthorized pets will incur a $500 penalty.br-No events, parties, or large gatherings.br-Quiet hours: 10:00 PM – 7:00 AM. Respect neighbors.br-Check-out by 11:00 AM. Late check-out requires approval.br-Please report damages immediately.br-Use the pool at your own risk. Not responsible for accidents or injuries.br-In case of emergency, dial 911.br-Must be at least 25 years old to book.br-Additional fees and taxes may apply.

Stunning 2BR/2BA Home with Private Heated Pool, Minutes from Siesta Key

Sarasota, Florida, United States

Bed

Bath

Sleeps

$310.75

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to many restaurants, grocery stores, Trader Joe’s, and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!brThe large bedroom has a super comfy California king bed and a single bunk. The family room is equipped with a leather sofa with a pull out full bed. The house is fully equipped with all basic cooking supplies, plenty of sheets, towels and beach towels even a cute beach bag. The kitchen has bench seating for 4 around a large island. The outdoor patio has a gas grill and seating for 4. On site parking for one vehicle is provided. The property landscaping is beautifully designed with natural limestone and palms. The mango house is the front house in a duplex. Each house has their own private entrance, parking and yard space.brThe property has perfect access to the center of Sarasota but is far enough away from the highway for peace and quiet. The neighborhood and region of the house is very safe and well kept.brbr

The Mango House Cozy Beach Cottage

Sarasota, Florida, United States

1

Bed

1

Bath

5

Sleeps

$104.5

Bay Street Bungalow-East is a stylish well-equipped studio and one half of a duplex located in the heart of downtown Sarasota within walking distance to shops, restaurants, museums, the City's largest park (featuring 12 Har-Tru tennis courts), and the Legacy bike/run/walk Trail that spans 20 miles. It is situated in the tree-lined artistic and emerging neighborhood of Alta Vista. The studio features a Murphy bed, convertible couch, full kitchen, marble shower, AC/HEAT, W/D and a private patio.brbrThe spacebrThe East Studio is a light-filled and peaceful studio sanctuary boasting all of the conveniences of home in an efficient space. It is approximately 350 square feet open plan and features a fully stocked kitchen, a Queen Murphy bed, a convertible couch, a cafe table for 2, a marble shower, private off-street parking (one car), and a private outdoor patio with a dining table (4). It can be rented by itself or with the West Studio (a mirror image in layout and style to the East Studio) should you want to travel with friends or family and be in close proximity. brbrThe East Studio gets plenty of light and also has up/down room darkening shades to protect you from the FL sun and provide additional privacy. The windows are hurricane-grade which creates a sound barrier. The East Studio does share an interior wall and exterior patio privacy wall with the West Studio so you may see other guests on property.brbrTo be clear, the unit does not have a separate bedroom area.brbrWe provide starter/limited toiletries (bath gel, shampoo, conditioner), paper towels, toilet paper, limited spices/oil, coffee filters, garbage bags, sponge and cleaning products. We ask that you clean as you go and keep the unit in good order. You can also hire our cleaning service should you wish to have interim cleaning services.brbrThe kitchen is fully stocked and features, pots, pans, dishware/glasses/flatware, bowls, a toaster, microwave, 12-cup drip coffee maker, a small oven/stove combo, and outdoor gas grill and more....brbrThere is a dedicated washer/dryer for each unit on site (outside and covered) for guest use.brbrWhile we love all pets, the space is suitable for and we can allow here: one dog (only) of less than 35lbs.brbrGuest accessbrGuests will have access to their portion of the Duplex (East Side), including the outside back patio (East Side), and East driveway & parking area.brbrOther things to notebrWhile each interior unit and back patio is private, please respect other guests throughout the exterior boundaries. Please avoid accessing areas beyond the East side front entrance, private driveway, and the hedging around the East back patio. We ask that each unit respects quiet hours, limits visiting guests to a total of 2 (no overnights for guests other than those renting the space via the platforms).brbrPlease avoid hanging clothes/towels or setting up chairs/tables in the front of the home or any boundary area of the home (not private to the interior or patio of the East unit), since this is a shared space for entry/exit for both units. While the interior wall between the units is concrete, it may be possible to hear some noise so we ask that each party be mindful of their sound when inside their respective units. We do not allow smokers or smoking inside or on the exterior of the property.brbrThere is a K-5 school across the street so be mindful of children that may be coming/going from school. At times there are announcements from the speaker and you can hear children playing while outside (inside the windows buffer most sounds).brbrWe store materials and vehicles on property in the far back yard and sometimes need to access this area during guest stays (via East driveway easement). This back storage and lawn area is off limits to guests. We will do our best to minimize any disruption when accessing this area. We also access the area to maintain the grounds.

Bungalow on the Park-East

Sarasota, Florida, United States

Bed

Bath

Sleeps

$447.97

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

3

Bed

3

Bath

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

4

Bath

10

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

$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

$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

$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

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

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

$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

$407.47

Welcome to my 4B/2BA luxurious coastal home right on a golf course, minutes to the best beaches in the world, airport and downtown areas.brbr• Pickleball courtbr• ️ Pool br• ⛳️ Putting greenbr• ️‍♂️ Backyard on the golf course, acclaimed Sara Bay Country Club br• Professional Basketball Hoopbr• ️ Minutes to the beachbr• Minutes to downtown Sarasota and Bradenton br• ✈️ 10 min to the Airport br• ️ Serene, quite, safe neighborhoodbr• High speed Wi-Fibr• ⭐️ Top community *Whitfield Estates*brbrMy home has a unique backyard, complete with a pool, pickleball court, putting green, professional basketball hoop, and BBQ, all right on Sara Bay Country Club golf course. 1,855 sq ft, it’s open and airy layout can accommodate up to 8 people. brbrShort drive to the beach, airport, downtown Sarasota and Bradenton. brbrThe pool heat can be turned on Oct-June for an additional daily charge. The home has been refurnished with brand new MLILY mattresses, an Article sofa, and decor throughout. brbrInside the kitchen, you’ll find new stainless steel appliances, silverware, pots, pans and plates for your stay. brbrAll bedrooms and the living room have new Roku TVs. brbrAmenities also include fast Wi-Fi, towels, soap, paper towels, shampoo, conditioner, and body wash. brbr2 King Beds, 1 Queen Bed, and 2 Twin Beds. The home is one story.brbrSecurity cameras are in place to ensure the safety of the guests and secure the property. They are located outside the front door, driveway, pool area, and garage. The garage is not part of the Vrbo - it is off limits, and guests can’t go inside the garage or park there.

GOLF COURSE BACKYARD, Heated Pool, Pickleball, Putting Green, BBALL

Sarasota, Florida, United States

Bed

Bath

Sleeps

$236.03

Relax in our bright, comfy beach house—just 10 minutes from Siesta Key Beach! We’ve got you covered with all the beach-day gear: chairs, umbrella, cooler, toys, and a wagon to haul it all. After a day in the sun, fire up the grill, play cornhole, or relax in the spacious backyard with a drink in hand. Guests rave in their reviews—this is the perfect spot for families, couples, and business travelers looking for comfort, fun, and a slice of Florida paradise.brbrLiving RoombrbrBright and open, the living room is perfect for family time. Enjoy DirectTV with Live TV, fast Wi-Fi, and 5 TVs throughout the house so everyone can watch what they like.brbrKitchenbrbrCook with ease in the fully stocked kitchen, now with brand-new pots, pans, and bakeware. Whether it’s a quick bite or a family feast, you’ll have everything you need.brbrDining RoombrbrGather for meals at the dining table or take it outside to the picnic table with umbrella for backyard dining.brbrBedroomsbrbrThe home features 3 bedrooms with queen-size beds, plus a Pack-n-Play for little ones. Each room has a TV for added comfort.brbrBathroomsbrbrWith 2 full bathrooms, mornings and evenings are a breeze. Fresh towels and essentials are always ready for you.brbrBonus Room / OfficebrbrWork or unwind in the dedicated office/TV room—great for remote work, kids’ TV time, or hosting an extra guest with the queen air mattress provided.brbrBackyard & Outdoor FunbrbrUnwind by the pond with its tropical birds and turtles, grill dinner on the gas or charcoal BBQ, or challenge the family to a game of cornhole.brbrBeach Gear & LocationbrbrSkip the stress—we’ve got chairs, umbrella, cooler, toys, and a wagon for the perfect beach day. Just a 10-minute drive to Siesta Key Beach, with local cafes, groceries, and restaurants nearby.brbrThe entire house and garage is for guest use.brbrWe are available by text and phone whenever you need us.brbrThe house is located in a quiet neighbor while centerally located between Sieta Keyes and DT Sarasota. Its with in minutes to the several grocery stores and great restaurants. Guests have said it is great for families with young kids.brbrRecommending renting a car if you are staying in Sarasota. We found that Budget has good prices. Groceries stores and restaurants are minutes from the house. The closest beach is about 10 minutes away.brbrPlease note that the home does not allow booking by guest under 24. There is no smoking or parties allowed, and all guests must be registered.brAbsolutely no parties or underage drinking.brbrAll adult guests must be registered.brbrNo SMOKING of any kind in the house.brbrNo cats, all dogs must be fully vaccinated and house (potty) trained.brbrPlease do not have your personal mail sent to our home address.brbrPlease do not put food, coffee grounds, or grease down the sink.brbrPlease turn off back porch & side garage light by 10 p.m. (The light shines in the neighbors window).brbrIf you have any questions, feel free to reach out any time.

Bright, Clean Paradise 10 mins to Siesta Key

Sarasota, Florida, United States

Bed

Bath

Sleeps

$242.41

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to the Happy Gecko! brbr brbrEnjoy a memorable stay at a spacious 3-bedroom, 2-bath pool home located just 2.5 miles from Siesta Key Beach. This renovated property features a screened-in heated pool, fenced yard, and an outdoor shower, making it perfect for family gatherings. brbr brbrLOCATION HIGHLIGHTS: brbr- 2.5 miles from Siesta Key Beach brbr- Close to restaurants, grocery stores, and fresh produce market brbr- Quiet residential neighborhood brbr brbrPROPERTY FEATURES: brbr- 3 bedroom/ 2 bathroom pool home (1529 sq ft) brbr- Screened-in heated pool with outdoor shower, fenced yard brbr- Pool heat available upon request (extra fee) brbr- Pool door alarm for safety brbr- Outdoor dining area and BBQ grill brbr- Game room with ping pong table brbr- Laundry room brbr- Pet-friendly with prior approval (dogs only, pet fee applies) brbr brbrLIVING ROOM: brbr- 50 Smart TV with streaming options brbr- Comfortable seating with big windows brbr- High-speed internet brbr brbrKITCHEN AND DINING: brbr- Updated kitchen with stainless steel appliances brbr- Dining table for family meals, seats 4-5 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, wall-mounted TV brbr- Master ensuite bathroom: vanity with tub/shower combo brbr- Guest bedroom: two twin beds brbr- Guest bathroom: accessible by separate entrance from pool, vanity with step-in shower brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- Nearby restaurants brbr- Local grocery and fresh produce market brbr- Close to Siesta Key attractions brbr brbrIMPORTANT INFO: brbr- Family rentals only, no corporate or contractor rentals brbr- Monthly bookings required for January–March, start at beginning of month brbr- No mid-month to mid-month winter bookings brbr- No cats allowed brbr*Please note that we have a plumbing repair scheduled for Monday, April 13, 2026 between 8 - 12 pm. brbr brbrSOAK UP THE GULF COAST SUN AND RETURN EACH DAY TO THE COMFORT AND CHARM OF YOUR SARASOTA RETREAT!brbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Beach Living: 2.5 Miles to Sand! | Private, Fenced Home with Screened Pool

Sarasota, Florida, United States

Bed

Bath

Sleeps

$213.05

Welcome to Gulf Gate Poolside Retreat! brbr brbrA renovated 3BR/2BA home with a heated private pool, outdoor dining with a smart TV, and a quick drive to Siesta Key Beach. Sleep easy with a king, queen, two twin bunk sets with a trundle, and two queen sleeper sofas. The kitchen is fully stocked, there’s central A/C, and a washer and dryer. Pet friendly for up to two well-behaved dogs. brbr brbrLOCATION HIGHLIGHTS: brbr- Gulf Gate neighborhood in Sarasota brbr- Short drive to Siesta Key Beach, Lido Key, St. Armands brbr- Close to Downtown Sarasota and shops brbr- 12 miles from SRQ Airport brbr brbrPROPERTY FEATURES: brbr- 3 bedroom/ 2 bathroom pool home (1780 sq ft) brbr- Heated private in-ground pool (pool heat available for a fee) brbr- Fenced yard, outdoor dining with grill brbr- Driveway parking for two, garage space for one brbr- Central A/C and ceiling fans brbr- Washer and dryer brbr- Pet-friendly up to two well-behaved dogs (prior approval needed, fee) brbr brbrLIVING ROOM: brbr- Bright, comfortable space, couch doubles as a queen sofa bed brbr- Streaming-ready TVs, all you need is your log in brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with modern appliances brbr- Breakfast bar seats 4 and dining table seats 6 brbr- Outdoor dining by the pool seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, queen sleeper sofa, closet, wall-mounted TV brbr- Master ensuite bathroom: double vanity with walk-in shower brbr- Guest bedroom #1: queen bed, sliding doors to the pool, wall-mounted TV brbr- Guest bedroom #2: two twin bunk beds, one with trundle twin bed brbr- Guest bathroom: double vanity with tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbr- Close to Gulf Gate shops and restaurants brbr- Minutes to Siesta Key sugar-sand beaches brbr brbrIMPORTANT INFO: brbr- Quiet hours start at 10 pm brbr- No parties allowed brbr- No glass in or near pool, swim at your own risk brbr brbrCLEAN, MODERN, AND SET UP FOR EASY FAMILY TIME BY THE POOL WITH SIESTA KEY'S SUGAR-SAND BEACHES CLOSE BY. SEND US YOUR DATES AND WE'LL TAKE CARE OF THE REST.brbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Gulf Gate Poolside Retreat | Heated Pool | Space for the entire Family + Dog | Short drive to Siesta

Sarasota, Florida, United States

Bed

Bath

Sleeps

$376.66

New Listing. Check out our rental across the street Amazing Waterfront Home with Private Dock to see our over thirty 10/10 star reviews.brbrMid-century 2 bedroom/2 full bath home on very large corner lot lined with palm trees for added privacy. The open floor plan creates a seamless flow between the living room, dining area and pool. The newly finished terrazzo floors add a touch of elegance to the home while maintaining the original character. Home is air conditioned/heated and both bedrooms have king size beds and 55” 4k smart televisions. The full kitchen is well-equipped with newer appliances and brand-new washer and dryer.brbrThe house is designed to be spacious and airy, with large windows that let in plenty of natural light. The heated pool provides a refreshing escape backing up to a tranquil pond. This home is perfect for those who want to enjoy the best of both worlds - the privacy of a large lot and the convenience of being close to Downtown and Siesta Key Beach.brbrThe home also has a fitness room equipped bikes and equipment.brbr15% discount for bookings 30 days or more. $25/day for pool heating.

Remodeled Mid-Century Pool Home Close To Beaches and Downtown

Sarasota, Florida, United States

Bed

Bath

Sleeps

$147.4

Charming updated duplex villa where you can enjoy beaches, shopping, restaurants and downtown Sarasota nightlife! Recently updated with porcelain tile throughout. Updated main bath with new vanity, cabinet and toilet. Bring the kids and dog and create special memories. One car garage, modern amenities, fast fiber internet, fully equipped kitchen and an enclosed backyard. There are many sights to see and experience all within a short distance; aquariums, fishing charters, a comedy club, Selby Gardens and of course Siesta Key, Casey Key, Longboat Key and Anna Maria!! Enjoy your fun in the sun.

Get To the Beach! Only 5 miles to Siesta Key Beach!

Sarasota, Florida, United States

3

Bed

1

Bath