Vacation Rentals By Owner In Longboat Key, FL

$531.37

Sea Grape Inn #5- Beachfront Property

Longboat Key, Florida, United States

BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbr** Need to stay less than the minimum required nights Please contact us **brCheck out our online Reviews!brbrThe Sea Grape Inn is a boutique-style resort complex with 8 private condominiums located beachside, on the shores of the Gulf of Mexico, on Longboat Key. A perfect beach getaway!brbrBEACH VIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.brbrBeautifully remodeled and upgraded; condo 5 sits directly on the Gulf of Mexico Beach and benefits from its prime block location offering optimum views of the pool and the gulf.brbrThis fabulous 2nd floor 2 BD/2 BA condo has been exquisitely upgraded to the highest specification. A completely re-designed and updated kitchen, featuring new cabinetry, stainless steel appliances, beautiful quartz counters, new sink and faucet and increased open area with a breakfast bar for 4. The refreshed living room area has a flat screen TV, sofa bed and new furniture throughout. A private screened lanai off of the living area provides the most outstanding views of the pool, Gulf of Mexico, and stunning sunsets. The beautifully appointed primary suite offers a king bed, flat screen TV, and an improved private bathroom. The refreshed second bedroom suite has two twin beds, a flat screen TV and an improved private shower room. New tiled floors throughout the living areas, plenty of new storage, stylishly re-decorated to create a cozy and elegant home 'with a from home feel' at the beach.brbrThe Following *Required Fees are included in the total cost.br*Required $150 Departure Cleaning Fee. brbr*Required Conservation Fee of $10 per night will be charged due to Longboat Key Ordinances to protect Turtles.brbr*Required Damage/liability insurance fee $70 is mandatory and will cover any damages or missing items in the guest rental unit or property, as needed. This damage/liability enables The Sea Grape Inn to rent to guests without requiring a refundable damage deposit. brbrCANCELLATION POLICY:br~Cancel 91 days or more prior to arrival date, guest will receive a full refund less a $250 admin fee.br br~Cancel 31-90 days prior to arrival receive full reservation credit for a future booking valid for 1 year (less any booking fees). Original reservation pricing is not guaranteed. Guest will be required to pay the difference if there is a price increase for new booking dates.br br~Cancel 30 days or less prior to arrival, or a No-Show; No Refund Or Booking Credit will be provided.brSee house manual in rental

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2

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6

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$158.79

/ Nightly

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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4

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$231.55

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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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$184.03

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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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3

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$541.08

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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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Condo

Beachplace 4 - 304 by FGC

Longboat Key, Florida, United States

Beautiful beachview unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. This unit has large beds in both bedrooms. Great for 2 couples. Kitchen recently remodeled and all new windows and doors. brbrThe online system will only book 12 months out, so please call us directly if you wish to book further in advance.brbrOn the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility.brbrThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brRental includes Cable tv, Wifi, parking, water and electric.br1 Month minimum requiredbrbrRRR-00583.2023

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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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$182.62

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Condo

DIRECT Gulf Front view from the 4th floor condo at Tiffany Plaza

Longboat Key, Florida, United States

Looking to work remotely during the summer and fall Why not consider working right on the beach Direct Gulf Front Rental available for August through to November 2023 along with the month of March 2024. Gorgeously renovated custom condo, 2 bedrooms, 2 baths. The renovated kitchen is complete with marble countertops and a wine refrigerator! This beach retreat has everything you need to get away from it all. The master bedroom has king accommodations, closets.The guest room offers queen accommodations with a desk overlooking the Gulf of Mexico. In unit washer/dryer and high speed WI FI complete the picture. You will love sitting on the Lanai overlooking the turquoise waters of the Gulf for morning coffee or sunset cocktails. This stellar location is close to dining, shopping and cultural venues, either north or south! (Two minutes north of Publix). The community amenities include a lovely sheltered heated pool, BBQ grills, club room with ping pong table, lending library. One covered parking space included, and plenty of guest spaces. Bayfront Park is also just a short stroll south and has fitness classes, yoga, tennis and pickleball courts, basketball, playground and is a great place to watch the sunrise!

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$352.82

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Condo

Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access

Longboat Key, Florida, United States

Looking for a winter glow-up Welcome to Longboat Key—where sandy beaches, soft breezes, and that “I could really get used to this” island vibe turn even the coldest months into sunshine season. Your home base: a spacious 1600+ sq. ft. 2BR condo perched right over Crane’s Bay with front-row seats to postcard-perfect views (and the occasional surprise manatee cameo).brbrInside, you’ll find all the comforts of home—only sunnier.brMain Bedroom: King bed + private bath with a jetted tub worthy of vacation-level bubble bathsbrGuest Room: Two twin beds (aka the cozy kid zone or bestie bunk room)brLiving Room: Sleeper sofa for extra guestsbrSecond Bathroom: Easy access for everyone—no vacation “line for the shower” chaosbrbrA Kitchen Built for Vacation ModebrFully equipped with full-size appliances, roomy countertops, a breakfast nook made for slow mornings, and all the essentials—dishes, pots, pans, toaster, coffee pot, and utensils.brPlus, in-unit washer + dryer to keep swimsuits fresh and sandy footprints in check.brbrResort Perks to Keep the Good Times RollingbrHeated Outdoor Pool & Whirlpool (Dawn to Dusk)brPerfect for cold-weather refugees and sunset soakers.brTennis & Pickleball CourtsbrServe up some friendly competition—or just look sporty, no judgment.brBeach + Gear AccessbrAsk at check-in for our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing equipment.br(First come, first sun-kissed.)brPicnic & BBQ AreabrGrill, chill, and dine under the Florida sky.brLobby EntertainmentbrBooks, games, and videos—because even paradise has cozy indoor days.brbrBefore You Book, A Few Helpful NotesbrbrParking: No campers, motorhomes, or trailers. (We’ve got storage options—call us.)brSmoking: Allowed only on balconies or designated areas. Not inside.brPets: We love them too, but this property is pet-free.brOccupancy: Max of 6 guests, kiddos included.brHouse Rules: No pets, no smoking/vaping inside, no parties.brViews: your view may vary.brAge Requirement: 21+ to rent and check in.brMaintenance: If anything pops up, our team is quick on the fix.brbrOn-Site Office HoursbrMon–Fri: 8 AM – 4 PMbrSat: 9 AM – 5 PM

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$346.08

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Condo

Find Your Sunshine Sanctuary on Longboat Key

Longboat Key, Florida, United States

Welcome to your sunshine-soaked escape on Crane’s Bay—where every condo gives you room to breathe, stretch, and settle into full vacation mode. With spacious layouts of 1,600 sq. ft. or more, these two-bedroom, two-bath retreats are designed for families, friend groups, and anyone craving a little extra elbow room.brbrYour Home Base in ParadisebrMain Bedroom: King bed + private bath = your personal recharge zonebrSecond Bedroom: Two twins bedsbrLiving Room: Sleeper sofa for the extra tagalongsbrFully Equipped Kitchen: Full-size appliances, cookware, blender (hello, smoothies), toaster, teapot, and coffeepot—because vacation fuel mattersbrIn-Unit Washer/Dryer: Stackable, convenient, and ready for sandy swimsuitsbrbrResort Perks Worth Packing ForbrHeated Outdoor Pool + Whirlpool (Dawn to Dusk)brRelax, float, soak—repeat. Winter who brTennis & Pickleball CourtsbrPlay a friendly match or unleash your inner Serena—your call.brGear on DeckbrAsk at check-in about our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing poles.br(First come, first vacationed.)brbrLobby Fun ZonebrBooks, games, and videos for rainy days, quiet nights, or the kid who always needs “one more thing to do.”brPicnic + BBQ AreabrGrill up something delicious under the Florida sky.brbrGood-to-Know DetailsbrParking: No campers, motorhomes, or trailers. Call us for storage options.brSmoking: Allowed only on balconies and designated spots—not inside.brPets: We love them, but not here. No pets permitted.brMax Occupancy: Six guests total (yep, kids count).brHouse Rules: No parties, no pets, no smoking/vaping inside.brViews: Balcony views vary by unitbrbrAge Requirement: 21+ to rent and check in.brMaintenance: Things happen—our team works quickly to make it right.brbrOn-Site Office HoursbrMon–Fri: 8 AM – 4 PMbrSat: 9 AM – 5 PM

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Condo

2-Bedroom Beachfront Condo on Private Beach Longboat Key

Longboat Key, Florida, United States

Available for long-term rental, this 2-bedroom, 2-bath beachfront condo is located on a private beach in Longboat Key, ideally situated between Anna Maria Island and Sarasota. The community offers resort-style amenities while maintaining a peaceful coastal setting.brbrThe primary bedroom features a queen-sized bed. The guest bedroom includes a bunk bed with a full-size bed on the bottom, a twin on top, and a twin trundle.brbrThe unit includes air conditioning, an in-unit washer and dryer, and an open patio for enjoying ocean breezes. Residents have access to a community pool, on-site workout room, and beach chairs provided on the private beach. This well-maintained condo provides comfortable beachfront living for an extended stay.

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2

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6

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$189.98

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Apartment

Longboat Snowbird Getaway • Beach & Bay

Longboat Key, Florida, United States

Summary:brEscape winter in style at this beautifully updated 2-bedroom, 2-bath condo located in the intimate, bayfront Longboat Arms community. Designed with snowbirds in mind, this sun-filled residence offers deeded beach access across the street, scenic water views, and resort-style amenities—perfect for extended seasonal stays (60-night minimum).brbrKey Featuresbr- 2 Bedrooms / 2 Bathroomsbr- ~1,187 sq ft of open, comfortable living spacebr- Large picture windowsbr- Private screened lanai with tranquil bay viewsbr- Full-size washer & dryer in unitbrbrCommunity Amenitiesbr- Deeded Gulf of Mexico beach access directly across the streetbr- Heated swimming pool, clubhouse, and tennis courtsbr- Boat docks and private ramp for kayaks, canoes, and small boats (subject to availability)br- Shuffleboard court, BBQ area, and covered carport parkingbr- Quiet and friendly 45-unit community ideal for seasonal livingbrbrRental Termsbr- 60-night minimum stay (ideal for snowbirds)br- Fully furnished and turnkey readybr- No pets per community guidelinesbrbrAvailable seasonally (Winter, Spring, Fall availability – inquire for dates)brbrLocation Perksbr- Direct access to Longboat Key’s pristine beachesbr- Minutes to St. Armands Circle, Publix, and Sarasota’s arts and diningbr- Serene bayfront setting with views of Sarasota Bay and beyondbr- Perfect for snowbirds seeking sunshine, tranquility, and convenience

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$777.93

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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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12

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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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$194.53

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Condo

Charming 2-bedroom fully renovated condo on Longboat Key with bay/ocean views.

Longboat Key, Florida, United States

Make yourself at home in this terrific 2-bedroom Longboat Key retreat. Fully renovated in 2025 with a king bed, queen bed, and full bed, this condo is perfect for a relaxing getaway. Enjoy the soothing ambiance of the space, complete with modern amenities like WiFi, AC, and washer/dryer. The 2 bathrooms are equipped with a hair dryer, iron shampoo and linens for your convenience. brbrEnjoy our private beach access just 100 yards from the front door. The pool comes heated and kept at a nice 85 degrees year round. Enjoy our kayaks for exercise or fishing. Speaking of exercise, our complex offers a full tennis court.brbrFor your dining experience, we are 5 miles from Armands Circle. If you like French cuisine, you will enjoy Maison Blanc a Michelin star restaurant just across the road. brbrBook now and enjoy everything this condo has to offer.

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$467.75

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Condo

Charming 2 BR Longboat Key condo with ocean view - Flirty Flamingo

Longboat Key, Florida, United States

Located in the highly sought-after Beachplace on Longboat Key and professionally managed by Gulf Coast Vacation Rentals, this beautiful 2 bedroom, 2 bath condo is located on the top floor in Building 3 and is absolutely stunning! With a pleasant view from the balcony, you can relax with your morning coffee listening to the waves or enjoy a glass of wine and toast to the spectacular sunset. The master bedroom features a king-size bed, ensuite bath, flat-screen TV, and a lovely view. The spare bedroom offers twin accommodation, flat-screen TV, and access to the guest bath. This unit has been outfitted with all the comforts of home including cable TV and Wi-Fi.brbrAmenities at BeachPlace include a large Olympic size heated lap pool, a whirlpool spa, a clubhouse with a fitness center and wireless internet, 4 tennis courts, and miles of white sand beach. Looking for restaurants, shopping, and the arts... St Armand's Circle is just a five-minute drive and downtown Sarasota is less than 15 minutes away.brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties. No pets per HOA. Beach furniture is for the exclusive use of Beachplace residents/guests and their accompanied guests, and may not be used to store extra towels, beach bags, or other material. Tennis hours are 8 am to 10 p.m. Lights go out automatically at 10 p.m., so please plan accordingly. Tennis courts are for the exclusive use of Beachplace residents and their invited guests. Reservations/registration is required during the October to May season. Players may reserve one court per unit through the pool attendant, up to 24 hours in advance. A picnic area with a gas grill is available next to the pool area and tennis courts for residents and their guests. The grill may be used between the hours of 12:00 Noon and 10:00 p.m. Users are responsible for cleaning the grill and disposing of all trash. Pets of any kind are not permitted on Beachplace property. The only exception is guide dogs which are protected under the Americans with Disabilities Act. All Day guest's names and planned arrivals must be called into Security to inform the guards so their entrance can be assured.brbrYour reservation may require you to fill out a Home Owners Association application that may request personal details. Any application fees required by the HOA are non-refundable.

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Condo

Newly Remodeled! Directly Across from Beach ~ Condo

Longboat Key, Florida, United States

The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. The island has very little commercialization and there are no fast food chain, but yet still has all the conveniences wanted. brbrNo crowds, only a peaceful and relaxing beach that will feel as if it is your piece of heaven. This is a ground floor condo with one bedroom, one bath and ample parking. brbrThe condo contains a full kitchen, king bed, bath/shower, washer/dryer (coin operated), wood deck with dining table. We have a pack and play for the kids. We do not provide an air mattress for the unit, but you are welcome to bring one. We also do not have a sleeper sofa. brbrWe request no more than 4 people staying in the unit. Beach chairs and linens are provided. Enjoy watching a Live TV or Netflix on a 55 inch and 42 inch LCD TVs.brbrKeywords: condominium, one bedroom, great value. brbr

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$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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$475.54

/ Nightly

Condo

Gulf Front 1 BR with Great Room Awesome View End Unit 227 with 42' TV

Longboat Key, Florida, United States

Spend some time in paradise! Relax in a comfortable Laz Boy Recliner overlooking the Gulf. Enjoy breakfast while watching the dolphins play. Come see picturesque sunsets that seem surreal. Newly remodeled beach front two story condo offers an awesome full gulf view with private terrace. This one bedroom, KING size bed(amazing mattress), one bath condo, has a fully equipped kitchen (cherry wood cabinets, granite countertops, stainless steel appliances)2 flat screen TV's (1 TV in Bedroom & 1 in Living room 42') with DVD. There is also an extremely comfortable Murphy bed (queen size) in a cherry wood cabinetry along with a pull out sofa. brbr For convenience a washer/dryer is located in your condo. Free Wireless Internet, Beautiful heated pool equipped with comfortable lounge chairs, umbrella and Weber grill all offering the full gulf view for you to enjoy. A wonderful place to sit back, relax and enjoy the natural beauty of Longboat Key.br

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6

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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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4

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