Vacation Rentals By Owner In Sarasota, FL

Best kept secret! Uniquely suited for guests who requires both luxury and privacy, this gulf front home offers picture postcard views all day from all rooms. Located directly on the beach via private, gated road, it features beach to bay water access. Enjoy the famously beautiful Siesta Key sunsets nightly right from the lanai or upper level decks. Stroll on the unmatched private beach or take your coffee in the lush tropical gardens on the bay side. Launch a water adventure from the dock--boating, fishing, kayaking with access to Inter-coastal Waterway. Kayaks and stand-up paddle boards are provided. brWide open spacious kitchen and living area with en suite king bedroom on main level along with additional full bath, laundry on main level and on upper level--double full-size stackable units in master closet. Elevator access from the ground level to every floor. The main level lanai spans the gulf front side and can be enjoyed in all weather as it features sliding glass windows. A romantic and spacious gulf front primary suite plus another gulf front king + twin and third queen garden view bedroom are upstairs which share spacious hall bath. Main level primary with en suite bath plus full hall bath for living area access. All bedrooms feature walk out terrace or lanai for peaceful outdoor relaxation anytime. Since these photos, the upstairs and bedroom carpet has been replaced with beautiful luxury vinyl plank. The staircase has been revamped to include a lovely solid aluminum handrail and new carpet runner. The comfort and peace this home affords are beyond explanation in just a few words. brbrAptly named The Patient Heron for the oft sited Great Blue Herons which walk slowly along water's edge, this unique and luxurious home has only just been made available in the last four years. Many of our guests have become repeat guests. This is a very special place. It is exclusively offered for minimum one month stays January through March, two-week minimum April through December. Book your stay in paradise now! You will not regret it! Book this and score major points with the family!

Exclusive Private Residence on the Gulf of Mexico, a Premier Vacation Retreat

Sarasota, Florida, United States

Bed

Bath

Sleeps

$188.71

You'll have a great getaway at this intimate and peaceful space next to Siesta Key. Just minutes away from Siesta Key! Great location very close to downtown and beaches, with lots of stores and restaurants. This property is about a 5 minute drive from the beach, it is not walking distance. brbrThis space sleeps a total of 5 people. 1 bedroom which has a king bed and a huge sectional sofa. Also there is a queen pullout sofa in the living space. 1 bathrooms with shower/bath. Self check-in with keypad lock. There is self parking available for free right in the driveway in front of the house.brbrThere is a kitchen available for your use. It includes brand new appliances as well as all the necessities you may need for them. The refrigerator will always be stocked with fresh and cold water bottles for our guests. When you walk in you will also find a welcome basket with snacks. In the cabinets you will find everything you will need for dining and all the baking and cooking utensils you could possibly need. brbrThere is a laundry area inside of the master bathroom as well. brbrThere is a TV in the living room that has Netflix, Hulu, Disney+, and ESPN+ all provided for you. brbrThe home does have wifi which will be provided to you when you book. brbrThe master bedroom has a TV as well that includes all of the streaming services above. Your bed will always have fresh linens when you arrive. brbrThere is a lanai area in the front of the space with outdoor seating for you to enjoy. There is also a white gate to the right of the home that leads to a beachy hang out spot including a fire pit with chairs, lots of seating, and games. On the side of the home there is also an outdoor dining area on the deck and a barbecue grill available for your use. brbrThis home is very close to the water. Just minutes away from some of the best beaches in Florida.

Cozy Getaway Home near Siesta Key

Sarasota, Florida, United States

Bed

Bath

Sleeps

$207.92

This wonderful home in Sarasota offers 3 cozy bedrooms - 2 with queen beds and 1 with a full bed. With amenities like heating, brand new A/C (2025), WiFi, and a washing machine/dryer, guests can relax and unwind after a day of exploring. The 2 bathrooms feature a shower and a bathtub for added convenience. Cool off in the private in-ground pool. Only 20 minutes from Siesta Key Beach! Beach chairs and umbrella are on property for use. Fully fenced in yard for a private relaxing atmosphere and so the dog can run around. Within minutes to I-75, shopping, and restaurants. Experience what Sarasota has to offer with a stay at our lovely home.

Gorgeous 3/2 in Sarasota. Dog friendly, inground pool. 20 Minutes to Siesta Key!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$230.13

Welcome to your dream retreat! This beautifully adorned 3-bedroom rental unit is the epitome of comfort and style. Need an extra sleeping space No problem – we provide a blow-up mattress for your convenience. With a sprawling 1700 square feet of living space, including a dedicated computer and smart TV in the master bedroom, you'll have all the amenities you need for a truly indulgent stay. There is parking for up to 2 cars on the left side of the driveway.brbrIndulge in the ultimate relaxation with our amazing hot tub, perfect for soaking away the stresses of everyday life. With three TVs scattered throughout the unit and two fully equipped kitchens, you'll have plenty of entertainment options and culinary freedom.brbrRest assured, cleanliness is our top priority – our rental unit is meticulously cleaned by professionals, ensuring a pristine environment for your enjoyment.brbrNestled in the historic Pinecraft neighborhood, just a short 5-mile jaunt from the breathtaking Siesta Key beach, and within walking distance of local markets, restaurants, and cafes, this is the perfect location for your getaway.brbrGet ready to unwind and rejuvenate in style at our enchanting rental unit – your ultimate relaxation destination awaits!

Apartment

Spacious 3/3 Apt w/Hot Tub/75in TV/Mac Computer

Sarasota, Florida, United States

Bed

Bath

Sleeps

$233.6

Fling off your flip flops! Bungalow #2, lovingly called Boho is part of a private oasis of three separate bungalows. This 3 bedroom, 2 bathroom cottage has a new and fresh bohemian feel. Tucked away on the property , surrounded by oaks and nature, but only steps away from the pool and by-the- door parking. Enjoy a quiet setting, peace and solitude even though you're right in the city! brJust a 15-minute drive from the stunning Lido Beach and a 16-minute drive from the renowned Siesta Key Beach. Unwind in the inviting outdoor pool or explore the nearby St. Armands Circle, just a 9-minute drive away. Inside, you'll find a fully stocked kitchen with a stove, oven, refrigerator, grill, and all the essentials you need to prepare delicious meals. Enjoy the convenience of a washing machine and dryer, and stay connected with the property's high-speed WiFi and smart TV. When it's time to relax, cozy up in the living room, lounge by the pool or recline in the nature area. With two bathrooms, air conditioning, and all the necessary linens and toiletries, this vacation home offers the perfect blend of comfort and convenience. Embrace the great outdoors with the peaceful outdoor area, and make lasting memories in this charming Sarasota retreat.Comfortable, serene, clean and quiet. Come experience the boho bungalow life, Sarasota style! Close and convenient to the best Sarasota offerings!

Cool cottage in a Private Oasis. Boat Parking. Nature and seclusion.

Sarasota, Florida, United States

3

Bed

Bath

6

Sleeps

$297.44

BNB Breeze Presents: Diamond's Legacy!brSituated in the heart of Sarasota, this inviting Florida home offers a relaxing retreat with beautifully updated interiors and welcoming outdoor spaces. With its screened-in pool and thoughtfully designed layout, this property provides a serene setting perfect for unwinding, entertaining, and enjoying everyday comfort. Your amenity list includes:br- Private Heated Pool - heated at NO extra cost from Nov 21 - Apr 1stbr- Putt Puttbr- Pet Friendlybr- Kids Play Areabr- & More!brbrDiamond's Legacy offers a welcoming retreat designed for comfort, relaxation, and effortless Florida living. Step into the backyard and you're greeted by a sparkling private pool framed by sunset skies, a spacious patio, putting green, and a charming covered gazebo lounge—perfect for unwinding, dining outdoors, or enjoying long, easy evenings with family and friends. The home sits on a well-kept property that blends indoor and outdoor living seamlessly. The windows fill the interior with natural light, highlighting the open living spaces and creating a bright, inviting atmosphere. Thoughtfully arranged seating areas make it easy to gather, relax, and feel right at home. Whether you're soaking up the sun by the pool, enjoying a peaceful night under the gazebo lights, or relaxing inside after a day in Sarasota, this home offers a warm and comfortable escape designed for both connection and rest.brbrWe know, contracts aren't the most exciting part of your getaway, but to keep our home safe, we'll need you to sign a quick rental agreement upon booking (this will be sent to you, after you book) — then it's all fun from there! You can see what the contract looks like in the House Rules section. Note, check in details will not be sent until that contract has been signed.brbrTHE INTERIOR SPACEbr- One Story Homebr- Blazing Fast Wi-Fibr- Laundry Area w/ Washer + Dryer (Detergent Provided)br- Our home is stocked with clean and sustainable products and toiletries to give you and your loved ones a toxin-free stay!brbrKITCHENbr- Fully-Equipped Kitchen w/ Cooking + Baking Essentials (No Food)br- Coffee Machinebr- Dining Area w/ Table + Chairsbr- Stove + Ovenbr- Fridge + Freezerbr- Microwavebr- Toasterbr- Dishesbr- Silverwarebr- Glassesbr- Wine Glassesbr- Coffee MugsbrbrLIVING ROOM br- Spacious Living Roombr- Large Smart TVbr- Large Sofa + Recliners br- Coffee Table (Perfect for Game Nights!)br- Throw Pillows + BlanketsbrbrSLEEPING ARRANGEMENTS | 3 Bedrooms |br• Bedroom 1: King Bedbr• Bedroom 2: King Bed br• Bedroom 3: Two Twin BedsbrbrBATHROOMS | 2 Bathrooms |br• Bathroom 1: Full Bath located through Bedroom 1 with standing showerbr• Bathroom 2: Full Bath with shower/tub combobrbrThe property also offers a charming outdoor retreat perfect for both relaxation and family fun. A private pool provides a refreshing place to unwind, while the outdoor dining and lounge areas create inviting spaces to gather and enjoy the Florida sunshine. The gazebo (glowing softly with string lights) sets the perfect ambiance for evening conversations or quiet moments of rest. A gas grill makes outdoor meals effortless, and the dedicated kids' play area ensures little ones have plenty to enjoy as well. Thoughtfully designed and welcoming, this backyard oasis is ideal for creating lasting memories throughout your stay.brbrTHE EXTERIOR SPACEbr• Spacious patio with 6 person dining table. br• Gas grillbr• Gazebo with comfy cushioned lounge areabr• Sun Loungersbr• Putt Puttbr• Private yard with play area for kidsbr• Twinkling string lights to brighten up the outdoor, evening activities br• Private Pool (Heated seasonally: see below for more info)brbrDon't miss out on the opportunity to experience a memorable getaway at Diamond's Legacy. Book your stay today!brbrNAVIGATING THE AREA brThe Bay Runner is a new, open-air trolley that provides complimentary service seven days a week, until midnight, with multiple stops along the way between Lido Key, St. Armands Circle, and downtown Sarasota!brbrSEE HOW WE ARE GOING GREEN!brWe love the environment, and are doing everything that we can to minimize our carbon footprint. Sarasota has been voted one of the cleanest and greenest cities in the US! Here are a few ways that we are loving on the beautiful Florida environment, and welcoming you to join us!br• This stay is central to beaches, restaurants, and shops! We encourage you to use our loved public transportation system to make traveling easy, and eco-friendly!br• We use high-quality, sustainable mattresses and linens.br• All of our toiletries are eco-friendly, clean products that come with reusable dispenser bags to eliminate waste.br• We use LED lighting throughout the home to minimize electricity usage. br• Thanks to the natural Florida sunshine, you can soak in the sun that floods this home through all of the large windows, without using excessive home lighting during the day!br• Our home is in a great location for Instacart! Make grocery shopping for the family easy while saving on gas!brbrHere are a few of our favorite local attractions:brbrLOCAL ATTRACTIONSbr1. Pompana Park for Pickleball Courts!br2. Legacy Trailbr3. Siesta Key Beachbr4. Lido Key Beachbr5. Downtown Sarasotabr6. St Armands Circlebr7. AquariumbrbrGOLFbr1. The Meadowsbr2. University Park Country Clubbr3. Tatum Ridgebr4. The Founders Club (Private Club)br5. Longboat Key (Private Club)br6. The Ritz (Private Club)br7. IMG Academy Golf Clubbr8. Esplanade Golfbr9. WaterleafbrbrRESTAURANTSbr1. The Shore: Trendy waterfront restaurant with amazing seafood!br2. Connors: High-end restaurant without the high price tag!br3. Grillsmith: If you go here, you MUST get the plank grilled salmon!br4. Dry Dock: Waterfront Seafoodbr5. The Fish Camp: Wonderful seafood, but often very busy!br6. Baker + Wife: You will just love this fantastic restaurant.br7. Riverhouse Reef + Grill: Further away in Bradenton, but fantastic!br8. Der Dutchman: Fantastic home-cooked meals just down the road from you!br9. Summer Tap Juice Bar: The BEST A ai bowl in town!brbrCOFFEEbr1. Breaking Wave Coffeebr2. Perq: Do not expect syrups, just great coffee :)br3. Project Coffee (2 Locations)br4. Out About Coffee (O A)br5. Postal 98 CafebrbrGROCERYbr1. Detwilers Farm Markets: The best place to buy organic fruits and vegetables!br2. Publixbr3. Trader Joesbr4. Whole Foodsbr5. Fresh Marketbr6. Walmart GrocerybrbrADDITIONAL AMENITIES:brLinens for each BedbrTowels and WashclothsbrRoll of Paper TowelsbrBottle of Dish SoapbrTrash BagsbrCoffeebrLaundry Detergentbr2 Rolls of toilet paper, per bathroombrBath essentials - Body soap, shampoo conditionerbr*Please be prepared to bring any additional supplies that you will need during your stay.brbrPlease Note:brbr1. Upon booking, each guest will receive a guest rental agreement. This must be signed before the Guide Book (which includes access instructions for the property) is sent.brbr2. Pet Policy: We love your furry friends! A fee of $150 per dog must be paid BEFORE the guest arrival date. There is a max of 2 dogs on the property and a max weight of 50 lbs. per dog. Sorry, but no cats or exotic animals are allowed in the home. If evidence of an unapproved (or unpaid for) pet is located on the property, there will be a $500 non-refundable fine. Please clean up after your pet in the yard (bring your own doggy waste bags) and in the home. Additionally, any pet brought to the property must not be left unattended in the home. If they are left at the property alone, they will need to be kept in a pet crate.brbr3. No Smoking: If any signs of smoking are documented, the renter agrees to pay a $200.00 / per day.brbr4. Quiet hours for the property are between 10:00 PM and 8:00 AM. Please keep the noise levels down over this time.brbr5. There are NO LONG CHECK-OUT INSTRUCTIONS! We want for you to be able to fully enjoy every minute of your stay!brbr6. We offer complimentary 24/7 communication to ensure that your stay exceeds your expectations! Please feel free to reach out to us day or night, and we will provide you with a swift response.brbr7. Pool Heat: This property is equipped with pool heat. Heat is turned on from November 21st through April 1st and is included with your stay at no extra costs. The FL sunshine does an incredible job at warming the pool for stays outside of these dates. Any request for pool heat outside of these dates will be considered individually and will incur an extra fee.brbrCity of Sarasota Vacation Rental License #25-VR-000072.

Private Pool + Kid's Play Area | Diamond's Legacy

Sarasota, Florida, United States

Bed

Bath

Sleeps

$256.67

Welcome to our newly renovated and modern coastal home. Your family will be close to everything when you stay at this centrally-located home. Explore our #1 top-rated Siesta Key Beach just 15 minutes away, discover downtown Sarasota with its amazing art, restaurant, and local shops just 14 minutes away, or venture out to Sarasota-Bradenton’s University Town Center just 10 minutes away- full of restaurants, shopping, and Tiger Wood’s new mini golf experience: PopStroke. This home is the perfect home away from home to experience with your friends and family!

Sunny Relaxing Getaway Home - Central to Everything!

Sarasota, Florida, United States

3

Bed

Bath

6

Sleeps

$123.9

This is a cozy fully furnished condo of 553 sq. ft. that is equipped with colorful taste. It will be perfect to enjoy your stay in Sarasota!brbr** THE MEADOWS GOLF: Please note, golf course is not currently open to tenants **brbrJust renovated, it offers 1 bedroom, 1 bathroom, a patio, a fully equipped kitchen and a comfortable living room with a beautiful view of the surrounding vegetation, the pond, and the putting green.brbrEnter the condo (ground floor unit, like a townhome) and you will have a nice view through the unit.brbr★Bedroom:brBedsheets provided.brThe first room is the bedroom with artful decoration, tile floors, 2 night stands and light. The queen sized bed is comfortable and the windows are surrounded by vegetation for a restful night of sleep.brbr★Living Area:brFollow the hallway to the luminous living room with a peaceful view of the vegetation, the trees, a small pond and the putting green in the back.brYou will like the quaint decoration with vivid artwork, a comfortable couch, an armchair and TV.brbr★Kitchen:brPods and trash bags provided to start you off.brThe open-plan kitchen was fully renovated with a stove, oven, microwave, dishwasher, and fridge. The bar can comfortably seat 2 guests.brbr★Bathroom:brThe renovated bathroom features a large walk-in shower, sink and toilet.brbr★Laundry:brThe washer and dryer are located in the entrance of the condo.brbr★Pool:brResidents and guests can enjoy the communal heated pool.brbr★Outdoor Space:brOpen the sliding door to the patio with outdoor furniture and enjoy the view with the sunlight, peace and quiet.brbr★Parking:brYou can park your car outside, there's a designated outdoor parking. (no carport)brbr★Amenities:br The Meadows community is known for its scenic trails, which are perfect for walking, biking, and bird watching. For those seeking additional recreational options, the prestigious Meadows Country Club offers a separate membership that includes an 18-hole golf course, 18 Har-Tru tennis courts, a lap pool, dining options, and a variety of social events.brbr**Please note that these memberships are not currently open to tenants. Alternatively, Bobby Jones Golf Course is conveniently located just 2 miles from the condo, offering easy access to a premier golfing experience!** brbr★Location:brDowntown Sarasota is a 15 min drive. Lido Key and Siesta Key are a 25 min drive.brbr★ High Season Booking Policy (January 1 – March 31)brThis rental is available by calendar month only, with check-in on the 1st of the month. Guests may book 1, 2, or more consecutive calendar months. Thank you for your understanding!brbr★Additional Info:brThis rental is subject to Homeowners Association (HOA) approval, which may take up to one week.brPlease note that the HOA application fee is not included in the booking total. For U.S. applicants, the fee is currently $50 for a single applicant, $65 for a married couple, and $96 for two unmarried co-applicants.brbrFees for international applicants are higher. All amounts are subject to change.brbr★Important Notes & Rules:br- No pets allowed per the HOA rulesbr- No trucks, no commercial vehicle, no motorcycles - per the HOA rulesbr- No parties, non smokingbr- Ac cannot be lower than 70 F and heat cannot be higher than 77 F - Don't leave doors/windows open when AC/Heat is runningbr- Use pool at your own risk, no lifeguard on duty. Supervise children at all timesbrbr★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.brbrYour unforgettable getaway awaits!

Condo

NEW! Cozy 1/1 condo The Meadows Peaceful Pond View

Sarasota, Florida, United States

Bed

Bath

Sleeps

$137.34

Condo Association Approval Required. Application Will be sent after property is bookedbrbrWelcome to your new getaway in The Meadows, a beautiful and serene community in Sarasota! This spacious 2-bedroom, 2-bathroom villa is perfect for those seeking a comfortable and convenient living experience. As you step inside and down the hallway, you'll be greeted by the bright and airy living space with plenty of natural light. The fully-equipped kitchen is perfect for cooking up delicious meals while overlooking the beautifully decorated dining and living room. The master bedroom features a luxurious king-size bed and an en-suite bathroom, while the guest bedroom has two twin beds and ample storage space. There is a set of full size washer and dryer to make laundry day easy. Step outside onto the lanai and soak up the beautiful Florida weather, surrounded by lush greenery and the sounds of nature. As a resident of The Meadows, you'll have access to a variety of amenities, including golf, tennis, fitness, and dining options, ensuring that there's always something to do. The community is conveniently located just a short drive from Sarasota's world-renowned beaches, UTC shopping, and dining destinations, making it the perfect place to call home for those seeking the ultimate Florida lifestyle experience. Book this vacation rental today and get ready to fall in love with this beautiful villa!

Condo

Lovely 2 Bed 2 Bathroom Condo in a quiet lush area near the golf course

Sarasota, Florida, United States

Bed

Bath

Sleeps

$181.72

All-New & Updated Hotel Room-Condo at the Ramada Inn on 41. Upper Floor, Two large & comfy Queen beds, 70 Smart TV w/ cable channels, strong WIFI. All-New Shower, Vanity, Coffee/Tea bar w/ fridge and microwave. Heated Pool, Tiki Bar and Grill with daily meal and drink specials. Live music too! Beautiful Marina steps from your door...Bring your boat or rent one! Minutes drive to SRQ airport, USF, New College, IMG Academy, Downtown Sarasota, St. Armand's Circle & All area beaches!brbrThe spacebrEnjoy your trip with the hotel-vibe being part of the Ramada Inn. Tiki Bar and Grill with Huge heated pool is literally just outside your front door.brbrThis adorable room features all the amenities you can think of for your beach vacation and offers an unbeatable location. This home is ideal for families, business travelers, students or singles.brbrThis property can accommodate up to 4 guests with a bedding configuration as follows:brbr• Bedroom # 1: Queen Bed (2)brbrExclusive Amenities Include:brbr• Heated Poolbr• Onsite Tarpon Bay Grill & Tiki Bar w/ Live Music!br• Marina - Boat rentals availablebr• Secure parking in front of roombr• Free WIFI and Cable channelsbrbrApprox. drive times to airport and major attraction cities:br5 to 15 min - beaches, theater, restaurants, shopping, SRQ airportbr20 min - Outlet mallbr50 min - St Petebr60 min - TPA Airport/Port of Tampabr2hr - Disney WorldbrbrOther things to notebr- Breakfast is NOT includedbr- Daily housekeeping NOT includedbr- Dock Fee NOT included. $1.85 linear foot per night paid to front desk.br-Check out is by 11am. A check out after 12pm will be considered “late” and a $100 late check out fee shall apply.

Hotel

All-New, Private, 70 TV, Heated Pool, Tiki Bar & Grill

Sarasota, Florida, United States

1

Bed

1

Bath

4

Sleeps

$210.14

Located in the heart of Sarasota, this home boasts 3 bedrooms and 2 bathrooms. Enjoy a peaceful get away from the craziness of life at our beautifully renovated home. A fully stocked kitchen and coffee bar helps to make it easier for meals at home. Parking for 2 cars, wifi, and Smart Tv's add to the home away from home feel.brbrCome and relax at Ingram House!

Ingram House 2

Sarasota, Florida, United States

Bed

Bath

Sleeps

$600.74

The KingfisherbrBay-View unit with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bayfront lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moorsbr∙ The Balcony – bay views from balcony connecting bedrooms and living areabr∙ The Grounds – fishing causeway, private bay and beach access, lined by royal palmsbr∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sandsbr∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainmentbr∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balconybr∙ Activities – scooter, golf cart, bike and kayak rentals nearby br∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – perfect fit for all with resort amenities and trolley to all top attractionsbr brbrThe BeachbrOur beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.brbrThe LocationbrWith so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bayfront pool.brbrBedroom DetailsbrThis is a 2nd-floor unit with an elevator. This unit is newly remodeled and has two master bedrooms with bathrooms en suite plus a third bedroom. This includes one king bedroom, and two bedrooms containing two queen beds each (5 beds in total). The balcony runs the length of the living area and two of the bedrooms. Note - because two master bedrooms have bathrooms inside them, guests sleeping in the third bedroom have to enter either the first or second bedroom to access a bathroom. In the past this has not been an issue for our guests, but let's make sure it's not an issue for you.brbrBeach Gear ProvidedbrWe provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrImportant Resort Limitsbr1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional emergency parking space is available 1 mile away. 3) Baths are location inside two of the three bedrooms. If any of these limits are not a fit for you, please let me know, I have other properties available.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, private laundry, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Apartment

Gertrude's Siesta | Bayview Unit w/ Balcony, Pools & Private Beach!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$330.93

We are Matt and Val, and we purchased this home with a vision to create a warm, inviting space for individuals, couples and families to escape to and enjoy the Sarasota area, one of our favorite places in the world to vacation. Come see why we love it and stay in our spacious 2 bedroom, 1 bath home with a heated, private swimming pool in a quiet Sarasota neighborhood. Backyard has a large private pool as well as grass to play or enjoy the Florida weather. brbrEnjoy walking to nearby local restaurants, or hop in the car for a short drive to world famous Siesta Key beach. Lots of dining, shopping and entertainment within a 15-minute drive. Master bedroom has a queen bed, second bedroom has two twin beds and the living space has a pull-out bed, to sleep a total of 6. High-speed WIFI internet plus a desk in the living room area makes working remotely a breeze. The large kitchen is fully stocked for all of your cooking needs. brbrThis home is our family vacation home, so we stock and care for it with extra care. We know you will find everything you need to enjoy this home away from home!

The Coral Cottage close to all that Sarasota has to offer

Sarasota, Florida, United States

Bed

Bath

Sleeps

$363.67

Discover your dream vacation rental in the heart of Siesta Key, Florida, where coastal charm meets modern luxury. This stunning home offers the ultimate getaway, just a short walk to the pristine Siesta Key Beach and vibrant village with dining, shopping, and nightlife.brbrStep inside to find a spacious, light-filled living area designed for comfort and relaxation. The main floor features a dining area with towering 20+ foot ceilings and massive windows, a gourmet kitchen equipped with stainless steel appliances, wood cabinetry, and granite countertops, plus a breakfast bar overlooking the cozy living room. Here, you'll enjoy leather sofas, a streaming-ready TV, and views of your private heated pool and patio.brbrThe outdoor area is your personal oasis, complete with a dining set, lounge chairs, and the perfect spot to soak up the Florida sun or enjoy an evening under the stars.brbrThe home's layout is ideal for groups or families. The split level boasts a loft with a queen-size Murphy bed, a guest bedroom with a queen bed, and a full bathroom. The top floor features a luxurious master suite with a king-size bed, ample closet space, and an ensuite bathroom with a soaking tub, separate shower, and dual vanities.brbrConvenience is key with an in-home laundry room and half bath, while entertainment abounds with streaming TVs in every bedroom, the loft, and the living room.brbrThis Siesta Key vacation home combines modern amenities, prime location, and unbeatable comfort. Whether you're planning a family getaway, group retreat, or romantic escape, this Airbnb-style accommodation offers everything you need for an unforgettable stay. Message us with any questions or to book your slice of paradise today!brbrMINIMUM STAY REQUIREMENTS: 1 week, usually Saturday to Saturday minimum with the exception of 3 nights a maximum of 30-day in advance or during low season.brbrOptional Fees:brbrPool Heating: $105/week

Walk to the Beach & Village, Heated Pool Oasis, Spacious

Sarasota, Florida, United States

Bed

Bath

Sleeps

$187.88

Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very large open layout with plenty of space for entertaining. In the back this vacation rental home has a large private screened-in solar heated pool and lanai. Kids can play outside on the grass backyard. The master suite is furnished with King-size bed, 32 flat-screen LED TV, walk-in closet, and large tub. There is a separate living room, dining room and family room w/ 55 flat-screen LED TV. The two additional bedrooms offer one Queen-size bed and two twins among the two which share a bathroom. Slide open the grand sliding glass doors in the family, kitchen, and living rooms to open the home up to the pool and fresh breeze off the gulf.brbrMINIMUM STAY REQUIREMENTS:brOne month minimum with the exception of 2 week reservations a maximum of 30-days in advance.brbrOptional Fees:brbrPets: $200/pet Non-refundable fee and prior approval required.

1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool

Sarasota, Florida, United States

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Bath

Sleeps

$249.54

Whether you're looking to spend time by the pool or at the beach, 'Siesta Jewel’ is perfect for travelers on a memorable Floridian adventure and snowbirds seeking to escape the winter! Lounge in the home’s pleasant lanai or prepare a delicious meal on the patio’s gas grill. This 2-bedroom, 2-bathroom Sarasota vacation rental is also located in a quiet neighborhood just minutes away from golf courses, Marie Selby Botanical Gardens, Bayfront Park, and some of America's most beautiful beaches!brbr-- THE PROPERTY --brbrLanai | Gas Grill | Quiet Neighborhood | 4 Mi to Marie Selby Botanical Gardens | Near GolfbrbrBedroom 1: King Bed | Bedroom 2: King BedbrbrOUTDOOR LIVING: Private outdoor pool, pool toys, lounge seating, patio, beach chairs/umbrellas, boogie boardsbrINDOOR LIVING: Flat-screen TV w/ cable, leather sofa, ceiling fans, en-suite bathroom brKITCHEN: Stove/oven, refrigerator, microwave, dishwasher, dishware/flatware, cooking basics, coffee maker, Crockpot, toaster, blender, expansive counters, breakfast barbrGENERAL: Free WiFi, central air conditioning, towels/linens, washer/dryer, laundry detergent, hair dryer, trash bags/paper towels, keyless entrybrACCESSIBILITY: Single-story home, 1 step to enterbrFAQ: Quiet hours starting at 9:00 PM, 2 exterior security cameras (facing out), optional nightly pool heat fee (paid pre-trip, applied to entire stay)brPARKING: Garage (2 vehicles), driveway (2 vehicles), street parking (first-come, first-served)brbr-- THE LOCATION --brbrSAND & SUN: Public Beach Access (4 miles), Crescent Beach (5 miles), Sarasota Beach (6 miles), Siesta Beach (6 miles), Indian Beach Park (7 miles), Lido Key Beach (8 miles)brATTRACTIONS: Marie Selby Botanical Gardens Downtown Sarasota (4 miles), Bayfront Park (4 miles), Mote Marine Laboratory & Aquarium (8 miles)brGOLF: Village Green Golf Club (1 mile), The Palms Golf Club at Forest Lakes (2 miles), Bobby Jones Golf Club (5 miles), The Highlands Golf Course (7 miles), The Groves Golf Course (7 miles)brDAY TRIPS: Walt Disney World Resort (119 miles), Universal Studios Florida (126 miles)brAIRPORT: Sarasota Bradenton International Airport (8 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This single-story home requires 1 step to enterbr- NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the street, and a Ring spotlight exterior security camera located on the garage facing the street. The cameras do not look into any interior spaces. The doorbell camera records video and sound for 30 seconds when motion is detected by the device. The spotlight camera will turn on the spotlights and walkway lights for 3 minutes when activated by motion; it will also record video and sound for 60 secondsbr- NOTE: Please observe quiet hours after 9:00 PMbr- NOTE: There is an optional pool heat fee of $35/night (+ fees & taxes, paid pre-trip, applied to entire stay)

Sarasota House w/ Private Pool - 4 Mi to Beach!

Sarasota, Florida, United States

Bed

Bath

4

Sleeps

$217.75

Welcome to Your Dream Beachfront Oasis! Nestled on the coveted shores of Lido Key, this impeccable contemporary furnished beach condo Imagine waking up to the sound of waves and the scent of saltwater breeze every morning in this modern,brbr1 bed, 1 bath condo that spans over 1,100 sq ft of bright indoor space and a grand 30-foot long 200 sq ft Private balcony that spans the living room and the bedroom and accessible from both.brbrThis stylish unit has extensive upgrades and most importantly, the Lido Beach Club is considered one of the best on Lido Key. Seamless Indoor-Outdoor Living: *Enjoy a seamless blend of indoor comfort and outdoor serenity with an open-concept living area *Electric fireplace *View of dense foliage, tall palm trees, and the beach and Gulf views invoking a true tropical oasis *Fully equipped kitchen with stainless steel appliances, including: *Convection oven with a warming drawer *55-bottle wine cooler *Reverse osmosis water tap *Thoughtfully Furnished for Comfort and Style: *Three custom-designed closets *Impact floor-to-ceiling sliding glass doors*Queen-size sofa bed with a memory foam mattress and a large storage area *Iconic ‘Cherner’ style dining chairs for comfort and easy maintenance *48” round glass dining table that easily sits 6 *White leather contemporary recliner in mint condition for a perfect reading haven. Spacious bedroom features: *Versatile built-in desk/vanity table *King-size comfort-adjustable bed with high-quality mattresses *Custom-designed walk-in closet with lockable drawers and a wall safe for added security *Luxurious Bathroom and High-End Finishes: Spacious bathroom with 2 separate rooms featuring: *Quartz countertops *Walk-in shower with a rainfall shower head *Spacious linen closet *Gorgeous porcelain tile throughout the kitchen, living room, hallways, and bathroom Lido Beach Club Lifestyle | Highly sought-after community.brbr*Direct beach access *Tropical feel heated pool with exotic palapas. *Well-equipped fitness center. *Library room at the lobby with Pool table or ping pong table *Two separate storage units: -Lockable one conveniently located a few feet from the entry door of the unit. -Additional storage space for beach chairs *Designated sheltered parking spot Enjoy a drink next door at the Ritz Carlton Tiki Bar where you can relax with your feet in the sand Short walk down the beach to The Lido Beach Resort for: *Poolside lunch *Elegant dining at the beautifully redesigned Drift Kitchen and Bar on the top floor with sweeping views *3-minute walk to kayaking through the mangrove. * Free trolly that will take you to the world-famous St Armand's Circle and downtown Sarasota. *Fun shopping *Delicious dining *Entertainment brbrPrice shown is for 3 months. Discounts for 6 month, 12 months, and off-season rental. We hope you'll enjoy your stay at our luxurious beach condo.

Condo

Beachfront Oasis Lido Key Sarasota, 1-bedrm furnished condo WiFi, fitness rm.

Sarasota, Florida, United States

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Bath

Sleeps

$318.29

Escape to this thoughtfully remodeled midcentury home nestled in a waterfront neighborhood on the Little Sarasota Bay, where modern comfort meets the timeless allure of the past. Located just minutes from the pristine Siesta Key and Turtle Beaches, and the vibrant city of Sarasota, this is the perfect destination for those seeking relaxation, exploration, and the best of coastal living. Five minute drive or a short walk to local stores, shops and restaurants including Publix, Target, Starbucks, Costco, Total Wine, Sprouts, and Chick Fil A.brbrKey Features:brbrChic Midcentury Design: Step into a world of sleek lines, warm wood accents, and an aesthetic that pays homage to the golden era of design. This homes interior blends midcentury flair with contemporary amenities, creating an atmosphere of effortless elegance. Have your dinner and relax at night in the screened lanai. Stunning sunsets provide the backdrop for unforgettable moments of relaxation and reflection. At night you can hear the gulf lapping of waves across the bay on Turtle beach and see countless stars.brbrWaterfront neighborhood: You can bring your watercraft. Access to the intracoastal waterway for kayaks, canoes and stand up paddle boards is located within the neighborhood. A public launch for boats and jet skis is nearby. brbrBeach Enthusiast's Paradise: With pristine beaches just a drive or paddle away, sun-soaked days and salty breezes are yours to enjoy. Whether you're a beachcomber, a sunbather, or an avid water sports enthusiast, the options are as endless as the horizon.brbrProximity to Sarasota: Immerse yourself in the cultural riches of Sarasota, renowned for its arts scene, dining, shopping, and vibrant atmosphere. Discover galleries, theaters, and historic sites before returning to the tranquility of your private retreat.brbrAmenities:br • Spacious living areas with ample natural light br • Fully equipped kitchen with modern appliances and dining areabr • Cozy bedrooms designed for restful nightsbr • Outdoor seating, dining areas, and a barbecue grill for al fresco gatheringsbr • High-speed Wi-Fi, smart TVs, and entertainment options for downtime enjoymentbrbrNearby Attractions:br • Siesta Key Beach: A world-renowned beach with powdery sand and azure watersbr • Lido Key Beach: A blend of natural beauty and lively amenitiesbr • Sarasota Jungle Gardens: Explore lush landscapes and exotic wildlifebr • St. Armands Circle: Quaint boutiques, dining, and entertainment hubbr • Ringling Museum of Art: A cultural treasure trovebrbrYour Midcentury Haven Awaits!brWhether you're seeking a serene escape, a beach lover's paradise, or an adventure in Sarasota's vibrant scene, this midcentury retreat is your perfect home base. Book your stay now and embark on a journey of relaxation and discovery.

Midcentury Waterfront Neighborhood Oasis: Beaches and Sarasota Charm

Sarasota, Florida, United States

Bed

Bath

Sleeps

$300.34

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Private Home 2 Miles from Siesta Key! brbr brbrThis newly renovated 2-bedroom, 2-bath private home in Sarasota is perfectly located just 2.2 miles from Crescent Beach (access #12) and close to local favorites like Captain Curt's Sniki Tiki and Jake’s Ice Cream. Enjoy modern comforts, a single-car garage, and ample driveway parking for extra vehicles or a trailer/RV. Perfect for a relaxing beach getaway with everything you need at your fingertips! brbr brbrLOCATION HIGHLIGHTS: brbr- 2.2 miles to Crescent Beach, Access #12 brbr- 3.7 miles to Siesta Key Beach & Pavilion brbr- 2.2 miles to Captain Curt’s Sniki Tiki Bar & live music brbr- .7 mile to Phillippi Creek & Oyster Bar, local favorite brbr- .6 mile to Phillippi Estate Park brbr- 2.2 miles to Walt’s Fish Market, local favorite brbr- 1.5 miles to Publix at Sarasota Pavilion brbr- 2.1 miles to Trader Joe’s brbr- 4.2 miles to Arlington Public Park, outdoor pool, tennis, gym brbr brbrPROPERTY FEATURES: brbr- Newly renovated 2-bedroom, 2-bath home (1316 sq ft) brbr- Single-car garage with opener, plus ample driveway parking brbr- Whole house water softener brbr- Outdoor hot/cold shower brbr- Large screened back patio with ceiling fan brbr- Open backyard and patio, outdoor electric grill brbr- Dedicated WIFI, central AC brbr brbrLIVING ROOM: brbr- Comfortable sofa and leather chair with ottoman brbr- Reading area with swivel rocker chairs and side table brbr- Smart Sony TV with YouTube included brbr- Airy sunroom with queen sleeper sofa (air mattress included) brbr brbrKITCHEN & DINING: brbr- Stainless steel appliances, soft white & gray stone countertops brbr- Mission-style dining table for six, plus 2 seats at the breakfast bar brbr brbrBEDROOMS & BATHROOMS brbr- Master bedroom: King bed (low profile), en-suite bath, rain shower, hand-held wand, solid stone countertop, ample storage brbr- Guest bedroom: Queen bed, wall-mounted Smart Sony TV, large closet brbr- Guest bath: Solid stone countertop, vanity, tiled shower with soaking tub brbr- Queen sofa sleeper in sunroom for additional guests brbr brbrEXTRA PERKS brbr- Beach items included: a couple of beach chairs, a beach umbrella, and beach towels brbr- Twinkle lights on screened patio for evening ambiance brbr- Private washer & dryer in garage brbr- Ample space for trailer or RV parking (RV cannot be occupied, or hooked up to home's electricity) brbr brbrIMPORTANT INFO brbr- No pets, no smoking/vaping inside, garage, or screened patio brbr- Monthly rental minimum in season—book whole months only brbr- AC maintenance scheduled for Nov 17, between 1 - 3 pm. brbr brbrSAND, SUN, AND RELAXATION AWAIT—SECURE YOUR DATES TODAYbrbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Fully Renovated Refined Home, Tastefully decorated, Centrally Located, 2.2 Miles to Beach!

Sarasota, Florida, United States

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