Vacation Home Rentals By Owner In Longboat Key, FL

Showing 150 Of 150 Vacation Rentals

$2013.02

Steps to Beach-Full gulf views infinity pool-EXQUISITE! Ask @ seasonal specials!

Longboat Key, Florida, United States

Endless gulf views in newly constructed spectacular home with private infinity pool. This unit features a brand new modern kitchen with duel sinks, a 48 inch range, 2 indoor eating areas and 1 outdoor table. There is a fire table and a grill on the main deck overlooking beautiful views. All bedrooms are ensuite with beautiful tiled showers. It is located on the white sand beaches of Longboat Key with easy beach access. This home was designed for modern comforts. Guests will stay in new beds with fine linens and enjoy gorgeous views and deluxe accommodations. Tastefully decorated with luxury appointments, this house is sure to please. Located on the beautiful gulf coast of Longboat Key, the house is an oasis with a chef's kitchen, gorgeous finishes and easy beach living. Ask about flexibility in stay requirements. Arrangements can be made for private chef, cleaning and concierge services.

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$231.55

/ Nightly

Private Vacation Home

Sutton Place with Private Beach, Pavilion with Grills/Showers, 2 Pools

Longboat Key, Florida, United States

Escape to paradise with this beautifully furnished 2-bedroom, 2-bathroom townhome on Longboat Key, Florida. With a beachy vibe, fantastic amenities, and a prime location, this coastal retreat offers the perfect setting for a memorable vacation.brbrSituated in a quiet community, this townhome provides access to a gated Gulf Beach pavilion just across the street. Here, you can enjoy the convenience of picnic tables, restrooms with hot showers, a car wash area, and lockers for your beach chairs. Spend your days basking in the sun and feeling the sand between your toes on the stunning Gulf Coast beaches.brbrBack at the townhome, you'll discover two swimming pools, one of which overlooks Sarasota Bay. Take a refreshing dip in the sparkling waters, soak up the sun on a comfortable lounge chair, or simply relax and admire the breathtaking views. The pools offer a serene oasis where you can unwind and escape from the worries of everyday life.brbrStep inside the townhome, and you'll find a cozy living room adorned with coastal accents. It features a comfy sofa, a large flat-screen TV, a love seat, and a small den with a glass-top dinette and a desk. This space is perfect for lounging, watching your favorite shows, or catching up on work while enjoying the beachy atmosphere.brbrThe dining room offers a wooden table with seating for four, providing a delightful spot to savor delicious meals. Additionally, three barstools at the kitchen counter offer additional seating options. The fully stocked kitchen boasts granite counters, white appliances, and all the necessary amenities to prepare and enjoy home-cooked meals. From casual breakfasts to gourmet dinners, this kitchen has everything you need.brbrThe primary bedroom is a tranquil haven, complete with a king bed, a SMART TV for entertainment, and an ensuite bathroom. The ensuite is equipped with a large walk-in shower, ensuring a luxurious and refreshing experience. The primary bedroom also features a light and bright sitting area, furnished with comfortable chairs where you can relax and unwind.brbrThe guest bedroom offers another inviting space, featuring a king bed, a SMART TV, and tastefully designed white dressers and end tables. It provides a comfortable retreat for your guests or family members. The guest bathroom includes a shower and tub combination, catering to everyone's needs.brbrAdditional amenities within the community include two heated swimming pools, with one conveniently located across from your unit. A clubhouse with a kitchen is available for community social activities or private gatherings. Three BBQ areas are scattered throughout the complex, providing a perfect spot for outdoor grilling and picnics. For those looking to explore the waters, kayak storage and launch facilities are also available.brbrExperience the best of Longboat Key living in this meticulously furnished 2-bedroom townhome. With its beachy vibe, array of amenities, and proximity to the Gulf Coast beaches, this vacation rental promises an unforgettable retreat in paradise. Come and make memories that will last a lifetime in this coastal gem.brbrSutton Place CommunitybrbrCentrally located on Longboat Key, Sutton Place offers guest a quiet and relaxing stay. Built in 1972, the community is home to 80 condominiums and townhomes Amenities include: two heated swimming pools with one located to the front of the complex, club house with kitchen for community social activities or your private party. Three BBQ areas are located throughout complex, kayak storage and launch are available. There is a gated Gulf Beach pavilion with picnic tables, restrooms/hot showers, car wash area and lockers for your beach chairs is located across the street.brbrLongboat Key Life brbrLongboat Key is a quieter gulf-side retreat located between Lido Key and Anna Maria Island along Florida's southwest coast. The barrier island is surrounded by the beautiful Gulf of Mexico and Sarasota Bay. The island's eastern shoreline is covered in mangroves with hidden canals and marinas. On the western shoreline, you can walk for miles on the white sandy beaches and swim in the gentle gulf. Imagine spending your days beachcombing, snorkeling, kayaking, paddle boarding, fishing, sailing, golfing, or cycling along the island's winding bike path.brbrLongboat Key is known for its abundance of dining options. With the Gulf and Sarasota Bay in its backyard, many restaurants focus on serving local, fresh seafood while visitors enjoy amazing waterfront views.brbrJust south and across the bridge is bustling St. Armand's Circle, a popular destination filled with boutiques, cafes, restaurants and tropical landscaped courtyards. Head north on Longboat Key, cross the Longboat Pass bridge, and find yourself on Bradenton Beach, Anna Maria Island and Holmes Beach. This area offers gorgeous, white sandy beaches, crystal clear water, fun waterfront bars, restaurants and a variety of shops.brbrTown of Longboat Key: RRR-00691.2025

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$158.79

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Private Vacation Home

LBK Whitney Beach Retreat 1

Longboat Key, Florida, United States

Highlightsbr• Three-minute Walk to Whitney Beachbr• 1 Bedroom, 2 Bathroombr• 1 King, 1 Queen sleeper sofabr• Two heated community poolsbr• Community tennis, shuffleboard, and pickleball courtsbr• BBQ Grillbr• Built in wine/beverage fridgebr• In-unit washer and dryerbr• One assigned parking spot. Additional spots available on first come first serve basisbr• Beach chairs and a cart includedbr• Close to popular dining options and local shopsbrbrWhitney Beach Retreat 1 by Reel Coastal Propertiesbr6700 Gulf of Mexico Dr unit 140brLongboat Key, FL 34228brbrExperience the charm and tranquility of northern Longboat Key at Whitney Beach. Nestled in a sought-after bayside community with deeded beach access just across the street, this 1-bedroom, 2-bathroom condo offers the perfect balance of comfort, relaxation, and coastal living.brbrSpend your days unwinding by the community pool, playing a friendly match of tennis, or enjoying a cool drink under one of the shaded tiki huts on the private stretch of white sand beach. For the boating or fishing enthusiast, a community dock and boathouse are situated directly on the canal just steps from the unit offering a peaceful backdrop of Florida wildlife, where manatees and fish can often be spotted.brbrInside, the condo is completely renovated with luxury finishes, bright and airy beach-inspired style. The spacious living area flows seamlessly to a Florida room overlooking the lush grounds and canal, creating the perfect spot for your morning coffee or evening glass of wine. The full-size kitchen is fully equipped for home-cooked meals, while the two bathrooms—complete with modern updates—add convenience and privacy for guests.brbrWith Whitney Beach Plaza just steps away, dining and shopping are always close at hand. Beach chairs and umbrellas are provided for your use, making it easy to enjoy the legendary Gulf sunsets just a short stroll from your door.brbrWhether you’re seeking peaceful mornings, active afternoons, or romantic evenings, this Whitney Beach retreat has everything you need for an unforgettable Longboat Key getaway.brbrThe Whitney Beach Association offers additional amenities such as grilling stations, and kayak launch, making every day an adventure or a peaceful escape.brbrRoom Detailsbr- Master Bedroom: King bed, tv, and ensuite bathroombr- Living Room: Queen Pullout SofabedbrbrThere are no pets allowed in this home.brbr*Please note: 1 assigned spot with 140 painted on the ground. Additional spots available on first come first serve basisbrbrPlease Remember:brYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrRules:br • This condo requires an HOA application to be completed and emailed back to ReelCoastalProperties within 3 days of booking.br • No dog(s) are permitted in this home. No other animals are allowed without specific ReelCoastalProperties approval.br • No Parties/Unauthorized Events and absolutely No Smoking or VapingbrbrLBK Rental Permit: RRR-01430.2025 (30-day minimum rental period)

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Exceptional(62)

$184.03

/ Nightly

Private Vacation Home

Beach Cottage with a Private Hot Tub

Longboat Key, Florida, United States

Welcome to this beach cottage on Longboat Key directly across the street from beautiful white sand beach with private beach access and new hot tub! A great getaway for a peaceful beach vacation. Relax on the beach or soak in our private hot tub. Close walk to fine dining and a gourmet deli/grocery! A short drive to St. Armand's Circle, Anna Maria Island and downtown Sarasota. brbrIf you are looking for a beach getaway, our cottage is the place for you!

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$541.08

/ Nightly

Private Vacation Home

Private Heated Pool & Hot Tub Retreat - Longboat Key Coastal Living

Longboat Key, Florida, United States

Looking for a 3 month renter for January, February, and March or atleast January 2026. Limetree House. This fabulous newly constructed 4 bedroom 3 bath, saltwater pool home is located on the south end of Longboat Key. Spacious with an open floorplan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy flooring, this home has it all. The upper deck with a view of the refreshing pool during breezy afternoons or the covered deck downstairs which offers great shade.brbrRinse off in the enclosed, poolside, outdoor shower. Dock your boat at the end of the street and cook up your fresh catch in the outdoor kitchen. The high end, natural gas grill has a side burner and countertop with a refrigerator to chill your beverages. Ping pong and bocce ball complete the picture for hours of fun. Have cocktails on the pool deck while you wait for your table at the highly rated Dry Dock restaurant which is literally behind the trees across the street.brThe dining table sits (6) with (4) breakfast bar seats nearby. Two bedrooms have (1) Queen and (1) twin XL each, one quest bedroom has a Queen and the master has a King bed, all with large screen televisions. The home is equipped with a full house water filtration system and an additional reverse osmosis faucet in the kitchen. If you would like to use bicycles during your stay, pleas let us know and would be more than happy to help!brbrWe are in Sarasota and available by phone to help with any issues. There is a pool heat fee that we had to classify as `management fee`. There is also a non refundable pet fee.brbrIn lieu of a damage deposit, guests will be charged a fee of $14.00 a night to cover any damages up to $3,000.brbrA three minute walk takes you to the Quick Point Nature Preserve where you can explore the mangroves and secluded beach on the boardwalks or in a kayak. There are 12 public beaches on Longboat Key. The parking is limited making crowds unusual. The prime location of Limetree House makes it easy to walk, bike, Uber or just drop off. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events..Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack’s, Florida`s Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, MLB Spring training with the Orioles and the brand new Braves Stadium, Museum of the Circus, Children`s fountain at Island Park, Myakka River and Park, Sarasota Ballet (Oct-Apr), Van Wezel Performing Arts, Florida Studio Theatre, Sarasota Opera House, The Asolo Theatre, and Players Theatre. Leisure time can be spent on shops, galleries, golfing, tennis, ice skating, water sports like, fishing, snorkeling, kayaking, diving, jet skis, water skiing or leisure boating. You can spend the entire day at our famous St. Armands Circle with its award winning indoor or outdoor dining, upscale shopping, and galleries. Enjoy the south end of Anna Maria island as it offers several locations for live music most nights. People from around the world come to choose from one of our many famous beaches: Siesta Key, Longboat Key, Lido Key, Bradenton Beach, and Anna Maria Beach. The famous white sands of Lido Beach are just steps away, offering sunsets of a lifetime! Vacation here once and you`ll be back!brbrThis property is leased on a first come, first serve basis. If we reply the property is available, it is at that moment but may become unavailable before you can book it. We suggest you book as soon as possible to not lose your favorite vacation rental.brbrCovid-19 Cancellation PolicybrIn the event guests are unable to reach their rental destination due to Florida State or US Federal Government Travel Restrictions within 60 days prior, owner will offer the choice of a credit or full refund. In the event of a full refund there will be an 18% service fee on rent cost. A request for credit will only be considered between 59 days and 30 days prior to the arrival date. The credit or refund will only be available if the travel restrictions are current at the time of request. A credit or refund will not be considered if travel restrictions are imposed after the arrival date.brThere must be a minimum of (2) adults overbrthe age of 30 as named tenants. We do not lease to young adults without adults over the age of 30 on the premises. brbrIn lieu of a damage deposit, guests will be charged a fee of $14.00 a night to cover any damages up to $3,000.

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Private Vacation Home

581 Yardarm Lane by FGC

Longboat Key, Florida, United States

Rental located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 sq ft and contains 3 bedrooms and 3 bathrooms and a private swimming pool. Dining room has views to the water. Canal connects directly to the Bay and the neighborhood is located on the southern end of Longboat Key, convenient to St Armand's Circle and Sarasota. Bring your boat as a lift is included. Come stay a month or more. Master bedroom has a King bed, second bedroom has 2 twin beds and third bedroom has a queen.brbrNo pool cagebrbrBring your boat - Boat dockage included. No trailer parking available. brbrDogs may be allowed but must be approved at the time of booking. brbrbrRRR-00602.2023

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Exceptional(1)

$777.93

/ Nightly

Private Vacation Home

Paradise–Pool Home Close to Beach Jessmyth Estate on Longboat Key by RVA

Longboat Key, Florida, United States

Welcome to Jessmyth Estate compliments of RVA, on Longboat Key. Only three houses away from the beach, this home is located directly on a canal overlooking Sarasota Bay. The spacious floorplan allows the entire family to gather in one room, whether watching TV in the living room or having a snack in the kitchen. Enjoy your morning coffee on one of the numerous decks and catch a glimpse of a manatee floating by or tropical birds cascading through the sky. The luxurious master suite features a spacious sitting area with views of Sarasota Bay from the large king-size bed. The guest suite includes a kitchenette and sitting area – the perfect place to retire after spending a day exploring Longboat Key. Each bedroom of Jessmyth Estate includes a deck overlooking the bay, a TV, and a full-size bathroom for added privacy and relaxation. With four bedrooms, four bathrooms, two half baths and a den, Jessmyth Estate has everything you need for an upscale escape to paradise for the entire family! Beach access is located directly across the street, so you're never far from the pristine beaches of Longboat Key. Free pickleball courts are located next door at Bayfront Park as well as kayak rentals.brbrbrbrAccommodations: Four-bedrooms plus den, four full-bathrooms, two-half bathroomsbrbrbrbrLocation: 578 Jessmyth Estate, Longboat KeybrbrbrbrAmenities: Boat Dock, Grill, Private Pool, Washer/Dryer, Kitchen, Decks Off Bedrooms, Wireless Internet, Beach Access, Guest Suite with Kitchenette, Full bathroom off each bedroombrbrbrbrBedding: Master: 1 King + 1 Twin Sleeper Sofa | Bedroom #2: 1 Queen | Bedroom #3: 1 Queen + 1 Twin Sleeper Sofa | Bedroom #4: 2 Full + 1 Queen Sleeper Sofa | Den: 1 Queen Sleeper SofabrbrbrbrView: Bay ViewsbrbrbrbrMinimum Night Requirements: MonthlybrbrbrbrOther: Additional electric and/or pool heat charges may apply; please call our local offices for details.

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Select Dates for Price

Private Vacation Home

Coastal Elegance by FVC

Longboat Key, Florida, United States

Welcome to Coastal Elegance managed by Florida Vacation Connection! brbrExperience unparalleled luxury in this magnificent 4-bedroom, plus office, den, and fitness room, 5.5-bathroom estate located on the highly sought-after Putter Lane in the prestigious Country Club Shores on Longboat Key. Managed by Florida Vacation Connection, this property spans over 5,300 sq. ft. and is designed to impress from the moment you arrive.brbrThe grand paver driveway, surrounded by lush, meticulously maintained landscaping, leads you to the stately double-door entrance. This residence features double garages with tiled floors, accommodating up to six vehicles.brbrStep inside and be captivated by the meticulous attention to detail. Architectural elements such as sleek curves, stately columns, and soaring ceilings create an ambiance of timeless elegance, while expansive glass walls frame breathtaking water views. The crown jewel of the home is the two-story glass wall that overlooks the infinity-edge pool, where playful manatees and dolphins are a common sight, making this home a nature lover’s dream.brbrThe open floor plan is perfect for entertaining. A large circular bar seamlessly connects the sophisticated living area to the gourmet kitchen, which boasts stone countertops, rich wood cabinetry, two wine fridges, and top-of-the-line stainless steel appliances. The adjacent dining area offers panoramic views through floor-to-ceiling glass walls, ensuring every meal is accompanied by a stunning backdrop.brbrRetreat to one of two primary suites—one on each floor—each offering luxurious walk-in closets and spa-inspired bathrooms with dual vanities, spa tubs, and separate showers. The guest accommodations are equally lavish, providing comfort, space, and privacy for all.brbrBoating enthusiasts will appreciate the direct bayfront access, complete with a private dock and a floating kayak launch, offering seamless access to the Bay (Please note boat lift is for owner use only.). The elevated pool area is a tropical oasis, perfect for lounging or entertaining, with ample space to enjoy the stunning water views.brbrLocated just moments from the world-class shopping and dining of St. Armands Circle and a short drive to downtown Sarasota's vibrant cultural scene, this property is ideally situated for those seeking the pinnacle of coastal living. Indulge in this extraordinary vacation rental where luxury meets the serene beauty of the Suncoast.brbrRRR# RRR-01224.2024

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Exceptional(21)

$327.7

/ Nightly

Private Vacation Home

Island Living on Longboat Key 3 minute walk to the beach!

Longboat Key, Florida, United States

Longboat Key Island Fun in a newly updatedbrbeautiful property!brNewly updated 3 story townhouse on beautifulbrLongboat Key with two bedrooms and two and abrhalf bath sleeps 5 guest comfortably on King,brQueen and pullout single beds. This wellbrequipped property is ready and stocked withbrbeach chairs, a cooler, a beach umbrella, and pullbrbuggy for your convenience. brRelax in this calm, stylish space that’s also walking distance from the beach!

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$885.06

/ Nightly

Private Vacation Home

Villa Sereno Summary:

Longboat Key, Florida, United States

Summary:brWelcome to the picture-perfect, social media dream that is Villa Sereno by LUXVP. brThis 5-bedroom, 4.5 bathroom canal-front home is elegantly decorated and thoughtfully curated to include everything needed for a relaxing Florida retreat. The owner has thought of every detail from the comfortable furnishings to the personal device outlets by each bed, and everything in between to ensure every guest of Villa Sereno has the vacation of a lifetime. When you enter the home you step into the spacious living room area with vaulted ceilings and open concept viewing. Your formal dining room to the left is large enough to seat a crowd with ample space. The kitchen area is just off the dining room with every kitchen amenity one could possibly need. A family room is located off the kitchen with a comfortable couch -- the kind you can melt into for a relaxing evening. Off the back of the kitchen is the laundry room and a half bathroom. Traveling back through the kitchen and breakfast dining area your eyes immediately take in the breathtaking pool and canal-front views. Off the kitchen is a set of stairs leading up to a private guest bedroom with bathroom en-suite and a private balcony overlooking the front of the property. Back through the living room to the right is a fully-stocked office complete with printer capabilities, a desk and everything needed for a home office space. The next door includes the guest-accessible non-usable single-car garage (located on the west end of the property) but this garage is no ordinary garage. It comes stocked with bicycles and kayak supplies for the athletic members of your group. Still traveling down the hallway is another guest bedroom with en-suite bathroom, a separate full-size bathroom and a third guest bedroom with direct pool access and views. Traveling up the beautiful main staircase includes a game room with ample activities and TV watching with water views that might distract you from anything electronic. To the front of the house is another guest bedroom with bunk beds and supplies that make it the perfect spot for traveling kids. Another half bathroom is off the main hallway, with the master bedroom located upstairs to the back of the house. As you would expect, the master bedroom spares nothing in its pursuit of being amazing including a spacious layout, walk-in closet with ample storage plus an en-suite bathroom with a Jacuzzi tub and walk-in shower. The best feature of the master bedroom may be the private, open air patio located off the back of the house with canal, distant bay and pool views. We guarantee this will be a spot you retreat to unwind and relax. The outdoor pool is just as luxurious as the inside - including a full-size kitchen, large TV and plenty of seating. A private dock is available for fishing and viewing use along with 2 kayaks, paddles and life vests are provided. The boat lift is not available for guest use. Stop dreaming of your perfect vacation and start packing -- Villa Sereno is calling. Answer the phone!brAccommodations: 5-Bedroom, 5.5-BathroombrLocation: 524 Outrigger Lane, Longboat KeybrAmenities: High End Decor, On the Canal with Bay Access, Full-Size Kitchen with Wine Cooler, Office with Printer and Phone, Several En-Suite Bedrooms, Several Private Patios, Open-Air Pool with Removable Safety Gate, Hot Tub, Outdoor Kitchen, Grill, Outdoor TV, Driveway Parking, Wireless Internet, Audio System, Upstairs Game Room, Private Washer/Dryer, Fishing Dock (no boats permitted), 2 Kayaks for Guest Use, 4 Bikes for Guest Use, Keyless Entry, Private Assoc Beach Access less than 12 Min Walk Away, Outdoor Security SystembrBedding: 2 King Beds (Master and Off Kitchen Guest Suite) + 2 Queen Beds (Downstairs Guest Bedrooms) + 1 Full-over-Full Bunk BedbrView: Canal ViewbrGarage Note: Guests will not have use of the 1-car garage on the west end of the home. for parking but accessing the kayaks and bikes. The garage on the east end of the home is locked and not accessible.brbrThe Space:brA 4 digit door code will be provided prior to your arrivalbrbrGuest Access:brPrivate entrance. Driveway parking onlybrbrThe Neighborhood:brLocated in the highly desirable Country Club Shores residential community on the south end of Longboat Key.brbrGetting Around:brThe property is 12 minute walk the deeded beach access with pedestrian crosswalk. 10 minute drive to St. Armand's Circle. 20 minutes into downtown SarasotabrbrOther Things to Note:brThere is an instruction book kept in the kitchen on the bar countertopbrbrInteraction with Guests:brHost is available any time if needed.

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Most popular vacation rentals in Longboat Key

$884.08

/ Nightly

Private vacation home

Hidden Bay/Beach Paradise

Longboat Key, Florida, United States

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$746.18

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Private vacation home

Canal Front Home - 8 min walk to beach. RRR-00953.2023

Longboat Key, Florida, United States

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$747.69

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Private vacation home

Longboat Key home on the canal and a 5 minute walk to the beach

Longboat Key, Florida, United States

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$755.36

/ Nightly

Condo

LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach along the turquoise Gulf of Mexico.

Longboat Key, Florida, United States

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$767.89

/ Nightly

Condo

Beachfront 4th floor 4BR Longboat Key Condo With Stunning Gulf Views Paradise Sur Mer

Longboat Key, Florida, United States

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$861.14

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Condo

3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!

Longboat Key, Florida, United States

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$1148.84

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Condo

Beach Front Condo on Gulf of Mexico

Longboat Key, Florida, United States

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$2112.85

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Condo

Luxury Beachfront Living - St Regis Waterfront Residency - Longboat Key - Sunset Reflections

Longboat Key, Florida, United States

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$1196.70

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Condo

Renovated Beachfront 2 Bedroom Condo by FVC

Longboat Key, Florida, United States

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$739.37

/ Nightly

Condo

Stunning gulf front 6th floor Longboat Key Condo with endless views - Once Upon A Tide

Longboat Key, Florida, United States

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Vacation Home Rentals By Owner In Longboat Key, FL

$2013.02

$231.55

$158.79

$184.03

$541.08

$777.93

$327.7

$885.06

Rent a place that suits your needs

Most popular vacation rentals in Longboat Key

$884.08

$746.18

$747.69

$755.36

$767.89

$861.14

$1148.84

$2112.85

$1196.70

$739.37

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