Home Vacation Rentals By Owner In Sarasota, FL

Showing 880 Of 3494 Vacation Rentals
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$550.18

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Private Vacation Home

Tropical Sarasota Retreat - 2 Historic Bay Homes - 4 BR Total

Sarasota, Florida, United States

Experience the ultimate botanical garden retreat in the exclusive Sapphire Shores / Indian Beach neighborhood of Sarasota, Florida. This unique property offers two beautifully restored craftsman homes on a spacious 1/2 acre lot, providing the perfect combination of historic charm and modern comfort. Located just minutes from the Ringling Museum, New College, Downtown Sarasota, St. Armand's Circle, and the stunning beaches of Lido Key and Siesta Key, this property is ideal for families, groups, or remote workers seeking a serene and luxurious getaway.brbrProperty 1: The CottagebrCharming and beautifully restored, this craftsman cottage on prestigious Bay Shore Rd dates back to 1939. Retaining its original charm, the cottage features a working stone fireplace, vaulted ceilings, crown molding, original hardwood floors, and craftsman tile work in the kitchen. Modern updates include lightning-fast WiFi throughout the property. The cottage offers 2 bedrooms, making it a great vacation home for a family or a perfect tropical paradise for remote work. The screened-in porch, shaded by a giant Banyan Tree, provides a relaxing space to unwind. Enjoy the tropical garden setting with mango trees right outside the door.brbrProperty 2: The Main HousebrThis botanical garden retreat, also built in 1939, has been fully updated while maintaining its original craftsman details. The main house features 2 bedrooms, each with a private ensuite bathroom. The master bathroom includes a dual-head shower and a spa bathtub with jets. Additional spaces include a home office, library, separate reading room, and a working fireplace. The private screened lanai is surrounded by lush tropical plants and offers a tranquil place to relax.brbrCottage Amenities:brbr Fireplacebr Fully Stocked Kitchenbr Screened Lanaibr 1 King Bedbr 1 Queen Bedbr Beach SuppliesbrbrHouse Amenitiesbrbr Fireplacebr Fully Stocked Kitchenbr Home Officebr Screen Lanaibr Fire pitbr Beach SuppliesbrbrFeatures:br- Both homes offer beautifully landscaped tropical gardens with mango, lemon, lime, grapefruit, fig trees, and more.br- Easy access to Sapphire Shores Park and Indian Beach Park for sunset views, outdoor yoga, and kayaking.br- Proximity to Sarasota's cultural attractions, dining, and shopping at St. Armand's Circle, and the beaches at Lido Key and Siesta Key.br- Located in one of Sarasota's most prestigious neighborhoods, surrounded by multi-million dollar homes and the scenic Sarasota Bay.brbrWhether you're looking for a quiet retreat, a family vacation spot, or a place to work from paradise, this combined property offers the best of Sarasota's natural beauty and cultural amenities. Enjoy the privacy and tranquility of this unique botanical garden setting with the convenience of being just minutes away from all that Sarasota has to offer.brbrPet PolicybrSarasota Banyan Tree is Pet friendly for dogs up to 60lbs. Guests are allowed up to a maximum of 1 dog. There is an additional pet fee of $35/night/pet.brbrWhat's provided for your stay. Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. brbr**Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. br**Your inquiry on our property will be responded directly to your personal email. Please keep a lookout for our response so we may best serve your request.
Bed 5

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Bath 3

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Sleep 12

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$547.87

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Private Vacation Home

Charming 2-bedroom house in superb Sarasota with WiFi, AC

Sarasota, Florida, United States

The Modern Sandbar | Your Mid-Term Luxury Oasis in SarasotabrDiscover The Modern Sandbar, a contemporary, fully furnished 2-bedroom, 2.5-bathroom home designed for comfort, convenience, and luxury. Perfect for mid-term stays (30+ days), this upscale retreat is ideal for corporate professionals, traveling nurses, snowbirds, and remote workers looking for a sophisticated space to call home.brbrProperty Highlights:brbrPrivate Outdoor Haven: Relax in your private oasis featuring a sparkling pool, shaded seating area, BBQ grill, and outdoor dining space—perfect for unwinding after work or enjoying weekend downtime.brbrSpacious & Stylish Bedrooms: Two serene bedrooms with plush linens, light shades, and ample storage for extended stays. Each room is designed to offer maximum comfort and privacy.brbr2.5 Modern Bathrooms: Immaculate and spa-like, with premium fixtures and luxurious touches to enhance your stay.brbrChef’s Kitchen: Fully equipped with high-end stainless-steel appliances, dual ovens, and a sleek island with bar seating—ideal for cooking and entertaining.brbrWork-From-Home Ready: Stay productive with fast Wi-Fi, smart TVs, and an ergonomic workspace. Perfect for remote professionals balancing work and leisure.brbrPrivate Parking & Secure Entry: Driveway parking and gated entry offer added security and convenience.brbrPrime Sarasota LocationbrConveniently located just minutes from Siesta Key Beach and Lido Key Beach, The Modern Sandbar is positioned to offer easy access to everything Sarasota and Manatee counties have to offer.brbrBeaches & Outdoor Adventures:brbrSiesta Key Beach: 10 minutes away – World-renowned for its powder-soft white sand and crystal-clear waters.brbrLido Key Beach: 12 minutes away – Ideal for sunbathing, swimming, and kayaking.brbrLongboat Key & Anna Maria Island: 30-40 minutes away – Explore pristine beaches, local dining, and boutique shopping.brbrBike, Boat & Jet Ski Rentals:brbrSiesta Key Watersports: Jet ski and parasailing rentals for adventure seekers.brbrBike SRQ Rentals: Explore Sarasota’s scenic trails and neighborhoods by bike.brbrBayfront Yacht Works: Boat rentals and charters for exploring Sarasota’s waters in style.brbrTop Dining & Nightlife NearbybrSarasota is home to an eclectic mix of culinary experiences and nightlife just minutes from your door.brbrLocal Favorites:brbrThe Shore: Chic waterfront dining with fresh seafood and craft cocktails.brbrColumbia Restaurant: An iconic Spanish eatery with rich history and vibrant flavors.brbrOwen’s Fish Camp: A local gem offering Southern-style seafood in a laid-back setting.brbrIndigenous: A farm-to-table favorite serving inventive American cuisine.brbrBars & Nightlife:brbrPangea Alchemy Lab: Innovative cocktails in a speakeasy-style setting.brbrThe Gator Club: Sarasota’s top live music and nightlife destination.brbrThings to Do & ToursbrWhether you're seeking adventure or culture, Sarasota offers endless opportunities.brbrThe Ringling Museum: Explore world-class art and the stunning Ca' d'Zan Mansion.brbrMote Marine Laboratory & Aquarium: Perfect for marine life enthusiasts.brbrSunset Cruises & Dolphin Tours: Witness breathtaking Gulf Coast sunsets on the water.brbrGolf Courses: Enjoy renowned courses such as TPC Prestancia and The Ritz-Carlton Golf Club.brbrProximity to Major HospitalsbrIdeal for traveling nurses and medical professionals, The Modern Sandbar is located near leading healthcare facilities:brbrSarasota Memorial Hospital: 5 minutes awaybrbrDoctors Hospital of Sarasota: 15 minutes awaybrbrLakewood Ranch Medical Center: 20 minutes awaybrbrNearby Airports for Easy AccessbrTravel is effortless with these nearby airports:brbrSarasota-Bradenton International Airport (SRQ): 15 minutes awaybrbrTampa International Airport (TPA): 1 hour awaybrbrSt. Pete-Clearwater International Airport (PIE): 1 hour awaybrbrPerfect for Mid-Term StaysbrWhether you're on a corporate assignment, a travel nursing contract, or relocating to the Gulf Coast, The Modern Sandbar offers a tranquil, design-forward space that blends work and relaxation effortlessly.brbrBook your stay and experience Sarasota’s best in comfort, style, and convenience!
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$191.62

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Condo

Charming 2-bedroom, 2 story unit within a short walk to Siesta Key!

Sarasota, Florida, United States

Within a short walk to Siesta Key Island, this beautiful newly furnished and decorated condo in a boutique setting is a superb vacation rental for guests seeking an enjoyable and comfortable stay. The seamless flow from the dining, kitchen, living and 2 story enclosed lanai makes this unit perfect for entertaining or relaxing. brThe heated outdoor pool is steps away from the private screened in 2 story furnished lanai with an electric grill. With 2 bedrooms, including a king bed, attached bathroom and outdoor balcony, and a second bedroom offering both queen and full beds, this gorgeous property provides for ample relaxation. The dining area offers a large table with seating for up to 7. The full kitchen provides all of your essentials for many family meals. The living room includes a flat screen tv, cozy sofa bed, recliner and chair for plenty of seating. Have a seat at the kitchen bar or prepare drinks from the unique built in living room bar that includes a wine refrigerator. You'll find all the necessary amenities like a hair dryer, iron, washing machine, dryer, AC and heating. There are beach chairs and 2 brand new cruiser bikes ready for biking to the beach, bars and restaurants. brbrWe love our condominium and think it will help you experience everything Sarasota and Siesta Key has to offer.brbr*Bookings must be made a minimum of 30 days prior to arrival*br* First time renters at Key Point Village are required to submit an application for rent to the HOA which includes a background check. Fees for this application are $100.00 for the first two renters and $40.00 per additional adult. (Information and paperwork will be sent once rental is confirmed) br*Peak months January, February and March require minimum monthly stay**brbrbrbr
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Exceptional(9)

$216.59

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Condo

Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA

Sarasota, Florida, United States

This 2 BR/2 BA condo is located on the quiet end of Siesta key with beautiful direct views of the Gulf and Blind Pass located on the Inter-Coastal Waterway. Sit out on your lanai, listen to the sound of the surf and enjoy watching the boats pass by or, if you prefer, join in on the fun! The local marina offers various boat rentals including kayaks, paddleboards, and jet skis. Pull your boat right up to our community dock equipped with cleaning stations. Convenient launch area for paddleboards and kayaks also located on-premise. Walk just a few minutes to beautiful Turtle Beach or enjoy upscale waterfront dining just steps from your condo. brbrFree local shuttle allows you to explore Siesta Key with its many beaches (Siesta Key Beach ranked #1 in the US), restaurants and shopping areas. Take a short drive off the key and visit the world-famous St. Armands Circle located in Sarasota, known for its sophisticated shopping and dining with over 100 boutiques, specialty shops, galleries, and restaurants. Return just in time to watch spectacular sunsets over the ocean from the comfort of your own lanai. brbrThe condo has 2 bedrooms (1 king, 2 twin beds) and 2 full baths, fully equipped kitchen (everything you need to bring out the chef in you), living room with queen sleep sofa, 50” HDTV, Bluray player and printer for your business needs. WiFi and cable included. Additional TV located in the master bedroom. A pocket sliding glass door leads out to fully furnished lanai with ceiling fan. Direct views of the ocean and Inter Coastal Waterway as well as a view of heated swimming pool. Stackable wash/dryer located in the unit with additional washing facilities on-premise.brbrEverything you need to feel at home is provided including toiletries, cleaning supplies, dishes, iron/ironing board, hairdryer, vacuum, linens, pillows, beach towels, beach chairs, beach bag. We provide plastic ware for your convenience should you decide to grill outside and enjoy a meal poolside. brbrPlease note the winter high season, January - March, is a minimum three-month rental. All other dates can be rented on a monthly basis.br
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Exceptional(12)

$202.97

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Private Vacation Home

Chic downtown gem-The cocoanut hut , hot tub and bbq night

Sarasota, Florida, United States

WELCOME TO THE COCOANUT HUTbrbrWelcome to The Cocoanut Hut, a newly built three-bedroom, two-bathroom home designed for comfort, privacy, and relaxed coastal living. The entire house is yours to enjoy.brbrThe backyard is a true highlight, featuring a 50-jet hot tub set beneath a romantic pergola with flowing white curtains, offering a spa-like experience ideal for unwinding at the end of the day. Enjoy outdoor dining at the large table for six under a generous umbrella, relax on the lounge chairs, or prepare meals on the grill with built-in stovetop. Morning coffee, a book, and the gentle Florida breeze complete the experience.brbrThe home is centrally located just a short drive from Lido Key and Siesta Key beaches, Sarasota Bay, downtown Sarasota, and St. Armands Circle for dining, shopping, and evening strolls.brbrSet in a genuine downtown residential area with a mix of historic homes and newer development, the neighborhood reflects real Sarasota living. Once inside the home, guests enjoy a calm, private atmosphere designed for quiet evenings and effortless stays.brbr⸻brbr THE SPACEbrbrWe’ve carefully designed the home to ensure comfort and ease throughout your stay.brThe primary bedroom features a king-size bed with a high-quality memory foam mattress, 100% cotton sheets, and a cotton duvet. Towels are new, plush, and quick-drying—ideal for Florida’s climate.brbrThe kitchen is fully equipped for home cooking and includes a coffee maker and electric kettle. Beach chairs, beach towels, and umbrellas are available in the garage for your convenience.brbr⸻brbr GUEST ACCESSbrbrGuests have full access to the entire property, including washer and dryer. Entry is via an electronic smart lock at the front door.brbr⸻brbr♨️ HOT TUB & OUTDOOR USEbrbrThe hot tub is a premium feature and intended for relaxation.br • Showering before use is mandatory to remove sunscreen, oils, or soapsbr • Children must always be supervisedbr • Please follow the posted hot tub guidelinesbrbrIf the hot tub is left excessively dirty, an additional $50 cleaning fee will apply.brbrThe grill must be cleaned after use; failure to do so will result in a $25 cleaning fee.brbr⸻brbr HOUSE POLICIES (PLEASE READ CAREFULLY)br • Primary guest must be 25 years or olderbr • Maximum occupancy: 6 guestsbr • Quiet hours: 9:00 PM – 8:00 AMbr • Smoking or vaping is not permitted anywhere on the property ($500 fine)br • No illegal activities or partiesbr • Unauthorized guests are not permittedbr • Pets: small/medium dogs only (under 30 lbs), max 2, $100 non-refundable fee per petbrDogs are not allowed on furniture or beds and must be leashed outdoorsbr • Commercial photography or video recording is not permittedbr • A gardener may periodically access exterior areas only
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Exceptional(17)

$476.59

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Private Vacation Home

Casa Bella Vita | Walk to Crescent Beach, Semi-Private Heated Pool, & Four Balconies

Sarasota, Florida, United States

Casa Bella Vita | Walk to Crescent Beach, Semi-Private Heated Pool, & Four Balconiesbrbr Why You'll Love This HomebrStep inside Casa Bella Vita, where contemporary design and coastal charm come together to create a welcoming atmosphere. The spacious living area is the heart of the home, featuring stylish furnishings and an airy ambiance, perfect for spending time with loved ones. The open layout invites effortless conversation, whether you're lounging in the living room or enjoying meals in the dining area.brWith four balconies, a bright living space, and a two-car garage stocked with beach essentials, this home is designed for easy transitions between sand, pool, and time together indoors.brbr ‍ ‍ Perfect ForbrLarge families and groups of friends seeking close beach access, walkability to dining, and a spacious layout with multiple bathrooms.brbr ️ Imagine ThisbrStart your morning with coffee on one of the four balconies before making the short walk to Crescent Beach. Grab the provided beach chairs, towels, cooler, and caddy from the garage and settle in for a day on the sand. After the beach, cool off in the semi-private heated pool or gather inside in the open living and dining area. The fully equipped kitchen makes it easy to prepare meals, whether you're cooking for the whole group or keeping things simple between outings. In the evening, take a stroll to South Siesta Key Village for dinner and live music, or head back home for a few rounds of ping pong in the garage. When the day winds down, retreat to your private bedroom space, each thoughtfully designed for comfort after a full day in the sun.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath – Sleeps 2br• Bedroom 2: Queen Bed – Sleeps 2br• Bedroom 3: Two Full Beds + Two Twin Trundles – Sleeps 4br• Living Area: Queen Sleeper Sofa – Sleeps 2brbrAccommodates up to 10 guests.brbr Explore the Areabr• 0.1 Miles to Point of Rocksbr• 0.4 Miles to South Siesta Key Village – Dining, Shops & Entertainmentbr• 0.6 Miles to Captain Curt's Crab & Oyster Bar Siesta Keybr• 1.2 Miles to Crescent Beachbrbr⌛ Don't wait—Your stay includes peace of mind through our CottageClean™ program, featuring a six-hour deep clean followed by a detailed 35-point inspection prior to arrival.brbr Need To Know: Casa Bella Vita is part of a duplex property and may share a dividing wall, outdoor areas, and/or amenities with another unit. Guests have access to the right-side garage and driveway spaces, along with the second-floor living area. Contact us directly for more information regarding any shared space for this vacation home. This home has stairs. If anyone in your group has difficulty with stairs, please contact us prior to booking to discuss accommodations.brbrThe pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather.
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Bath 3

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Sleep 10

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$427.87

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Condo

Brand New Luxury Townhouse in Downtown Sarasota w/Elevator, Kayaks, and bicycles

Sarasota, Florida, United States

Perfect for the whole family, this beautifully appointed, three-bedroom condo is situated within walking distance of the exclusive boutiques, art galleries, and restaurants that downtown Sarasota has to offer. You'll enjoy all of the entertainment, nightlife, and shopping of the city from this convenient, yet secluded, location overlooking the Hudson Bayou.brbrIf you enjoy kayaking, there is no better location! Skip the parking costs and rental fees and take the kayaks that are provided for you down the canal, which is conveniently located in the backyard. Prefer riding a bike Take our bikes for a ride instead. Afterwards, feel free to take the beach chairs and umbrellas also provided to nearby Lido beach in order to soak up the warm Florida sun and calming ocean breezes.brbrAbout the property:brbrThe main entry door is located on the left side of the building with a second entry door located inside of the parking garage. The condo has an elevator, but guests must be able to walk up the steps leading to either entry door in order to enter the building. The first floor includes a bedroom with a full bathroom and access to the patio. The second floor includes the kitchen, a full bathroom, and the living room with balconies overlooking the canal. The third floor includes the master bedroom with its own balcony and full bathroom, the laundry space, as well as another bedroom and full bathroom.brbrParking Garagebrbr2 bikes, 2 kayaks, 4 beach chairs, and 2 beach umbrellas available for guests in garagebrbrShared pool access with neighboring condosbrbrPropane grill located in backyardbrbrWireless Internet Accessbrbr***Guest pets are not permitted.brbr***By booking this property, guest acknowledges that use of the swimming pool, adjacent bayou, and any watercraft including boats or kayaks is entirely at their own risk. The property owner assumes no responsibility or liability for accidents, injuries, or loss of life related to swimming, fishing, boating, kayaking, or any other water-related activities on or near the premises. No lifeguard or supervision is provided, and children must be supervised at all times. Guests are kindly asked to exercise caution and good judgment, and understand they are responsible for their own safety and that of their group while enjoying these amenities.
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$266.89

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Private Vacation Home

New! Waterside Lakewood Ranch, Tennis, Pool, Walk to Restaurants and More!

Sarasota, Florida, United States

Experience the best of Sarasota and Lakewood Ranch in this newly built, coastal-modern townhome in the sought-after Nautique at Waterside neighborhood. With serene lake views, top-notch community amenities, and walking access to the vibrant Waterside Place, this vacation rental offers the perfect mix of relaxation and convenience.brbrHighlights of the Homebr• Large well-designed open floor plan ideal for family gatherings with a seamless flow from the main living area to the kitchen and dining space.br• Beautifully decorated in a coastal-modern style, creating a fresh and inviting atmosphere for your stay.br• Spacious living room featuring a large sectional sofa, plush pillows, and a SMART TV for cozy movie nights and streaming your favorite shows.br• Gourmet kitchen fully stocked for all your culinary needs, with stainless steel appliances, ample storage, and a large kitchen island with two high-top chairs.br• Dining area comfortably seats four for family meals or casual gatherings.br• Private outdoor courtyard with a sectional sofa and dining table—perfect for alfresco meals, morning coffee, or unwinding under the stars.brbrBedrooms & Bathroomsbr• Primary suite with a king bed, seating area, SMART TV, ensuite bathroom, and luxurious finishes for ultimate comfort.br• Guest bedroom with a queen, whimsical bedding, and playful artwork.br• Third bedroom/office featuring a twin daybed, desk, and chair—ideal for remote work or extra sleeping space.br• Guest bathroom with a shower/tub combo, sleek vanity, and plush towels.br• Powder room conveniently located on the first floor.br• Full-size washer and dryer for your laundry needs.brbrCommunity Amenities & Locationbr• Lakefront community pool for refreshing swims.br• Tennis courts for active fun.br• Walking and biking trails that circle the lake with gorgeous views of the Waterside community.br• Two-car garage plus beach essentials provided for enjoying Siesta Key or Lido Key Beach.br• Steps from Waterside Place, where you’ll find coffee shops, restaurants, boutiques, a weekend farmer’s market, live music, and plenty of entertainment.brbrThis vacation rental combines modern luxury with a prime Sarasota location, making it perfect for families, couples, business travelers, or anyone seeking a stylish retreat near everything Lakewood Ranch and Sarasota have to offer.brbrPet Fee: This is a pet friendly home and allows 1 dog. Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $250 pet fee is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup!brbrAbout the NeighborhoodbrYou'll find plenty of family fun activities and entertainment at the pet-friendly Waterside Place! From the Sunday Farmer's Market providing local fresh veggies and shopping, to Ranch Night Wednesdays where the streets are lined with the best food trucks around and the area’s most talented local musicians at the pavilion overlooking the lake, along with exciting cornhole tournaments that make it ideal for fun and socializing with the locals. Just across the bridge from the pavilion you'll find Waterside Park with volleyball courts, hammocks, playgrounds, a waterpark, walking paths and Fitness in the Park with morning yoga. Every 2nd Friday the park also hosts a free family-friendly movie night.
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