Vacation Rentals By Owner In Longboat Key, FL

Experience the ultimate beach lifestyle with this ground-floor condo at Silver Sands Resort, where your back lanai steps directly onto the white sands of Longboat Key's private beach. Enjoy unparalleled access for shell collecting, sandcastle crafting, snorkeling, and the thrill of spotting dolphins right from your doorstep.brbrUnit Features:br- Master Bedroom: Private, with a king-size bed and flat-screen TV for ultimate relaxation.br- Living Area: Cozy with a queen sleeper sofa and another smart TV, seamlessly flowing into a fully-equipped kitchen perfect for dining at home or enjoying meals with the ocean breeze on your screened lanai.br- Outdoor Living: The lanai offers an unobstructed view of the Gulf of Mexico, ideal for leaving the doors open to enjoy the sound of the waves while cooking, reading, or sleeping.brbrResort Amenities:br- Heated Saltwater Pool: Just ten steps from your door, equipped with complimentary chaise lounges and umbrellas for your sunbathing pleasure.br- Recreational Activities: Engage in shuffleboard or mini-golf right on the property, ensuring fun for all ages.brbr- Conveniences:br - On-site laundry facilities for your convenience.br - Maid services available to keep your stay as relaxing as possible.br - On-site management to cater to your needs.br - Wagons: Provided for easy hauling of luggage or groceries from your car.br- Free Wi-Fi: offering unlimited internet access in your unit and throughout the resort for work, entertainment, or staying connected with loved ones.brbrNearby Attractions with Driving Distances:br- Busch Gardens: About an hour's drive north in Tampa, offering thrilling rides and animal encounters.br- Anna Maria Island: Just a 20-minute drive north, known for its quaint charm and beautiful beaches. Don't miss the shops on Bridge Street, where you can find unique boutiques, art galleries, and local eateries.br- Ringling Museum of Art & Ca' d'Zan: Approximately 15 minutes away in Sarasota, a must-visit for art and history lovers.br- Lido Key: A quick 10-minute drive south, perfect for beach days and local exploration.br- Sarasota Bradenton International Airport: Only 10-15 minutes away, making your arrival or departure seamless.br- Myakka River State Park: About a 30-minute drive east, offering a deep dive into Florida's natural beauty.br- MacDill AFB: Around an hour north in Tampa, an excellent opportunity to visit a family member serving at the base, or for those interested in aviation and military history.br- Aquarium of Florida (Florida Aquarium): Roughly an hour's drive north in Tampa, educational and fun for all ages.br- St. Armand's Circle- About 10 Minutes South with shops and restaurantsbr-Joan Durante Park: A short drive away, this park features scenic trails ideal for walking or biking, offering a serene escape into nature.br-Bayfront Park: Also nearby, this park provides basketball and pickleball courts along with kayak rentals, making it a hub for both sports enthusiasts and water adventurers.br-Dining Options: Numerous restaurants are within walking distance, offering a variety of cuisines to satisfy any palate right after your day by the beach or in the parks.br-Harry's Convenience Store: Located on Longboat Key, this store is perfect for grabbing beach essentials, snacks, or a cold drink, just a short distance from your condo.br-ABC Baby Rentals: For families traveling with young children, ABC Baby Rentals offers all the necessary baby gear from cribs to strollers, located in Sarasota but serving the surrounding areas, ensuring a comfortable and hassle-free vacation.br-Backyard Bike Rental: Explore the island in style with rentals from Backyard Bike Rental, offering a range of bicycles for all ages, conveniently located near the resort.brbrThis condo isn't just a place to stay; it's your personal gateway to the Florida beach experience where every moment is filled with luxury, leisure, and the soothing sounds of the sea, surrounded by a wealth of attractions easily accessible by car.

Beachfront 1-bedroom condo in Longboat Key, Private beach in your backyard.

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$374.22

Welcome to Little Gull Cottage—your laid-back coastal escape with just the right touch of charm. The spacious main bedroom features a king bed made for slow mornings, while the guest room offers a cozy queen bed for additional comfort. The living room includes a queen sleeper sofa, perfect for extra guests, along with a fireplace and plenty of seating for relaxing after a day in the sun.brbrStart your mornings with coffee from the well-equipped kitchen and enjoy it out on the porch, soaking in the peaceful surroundings.brbrPlease note: stairs are required for access, and parking is conveniently located underneath the cottage.brbrInside, you’ll find classic Cape Cod-inspired touches, while outside, Longboat Key brings the magic—think tortoises wandering by, egrets in the distance, wild parrots overhead, and even the island’s famous peacocks making an appearance. It’s all part of the experience.brbrAdditional Information:brbrHouse Rules: No pets, smoking/vaping, or partiesbrAge Requirement: Must be 21+ to rent and check inbrSecurity Deposit: Refundable hold at check-in, subject to inspectionbrAmenities: Occasional maintenance may occur; our team responds promptlybrbrOn-Site Office Hours:brbrMonday–Friday: 8 AM – 4 PMbrSaturday: 9 AM – 5 PM

Longboat Key Cottage Steps to Pool and Bay Dock

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$374.22

Escape the daily hustle and embrace tranquility at this charming cottage with breathtaking bay views. The spacious main bedroom features a king bed for ultimate relaxation, while the living room, with its cozy fireplace and queen sofa bed, offers additional comfort and ample space to unwind. Start your mornings by preparing a fresh coffee in the well-equipped kitchen and savor it on the porch, surrounded by serene bay vistas.brbrFor a complete relaxation experience, this cottage captures the essence of Cape Cod style, with its classic fireplace and inviting beach ambiance. Enjoy picturesque surroundings with tiki huts, straw roofs, and brick-paved walkways. brbrImmerse yourself in Longboat Key's natural beauty, where you might encounter vibrant wildlife like tortoises, egrets, wild parrots, and even the famous local peacocks. br*Please note that the cottage requires stairs for access. brParking is conveniently available under the cottage.brbrAdditional Information:brHouse Rules: No pets, smoking/vaping, or parties.brAge Requirement: Must be 21+ to rent and check in.brSecurity Deposit: А refundable hold at check-in, subject to inspection.brAmenities: Maintenance may occur; our team works promptly to resolve issues.brbrOn-site office hours:br8 am -4 pm Monday through Fridaybr9 am - 5 pm Saturday.

2BR Cottage Bayside Time for Relaxation

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$427.62

This spacious retreat features a king bed in the main bedroom, ideal for recharging after a day of beach adventures. The living room is your ultimate chill zone, with a queen sofa bed for extra guests, a cozy fireplace, and tons of seating for your crew. Whip up your favorite morning brew in the well-equipped kitchen and sip it on the porch while soaking in bay views.brbrReady for adventure The resort has you covered with a game room (pool and ping-pong, anyone , BBQ grills for your next cookout, bikes to explore the area, and even a boat dock for some serious fun on the water. Kids will love the playground, and who knows Maybe you'll spot some local wildlife like tortoises, egrets, or even the famous peacocks of Longboat Key.br*Stairs are needed to access the cottage.brbrWhether you're here to unwind or explore, this spot blends classic Cape Cod style with those iconic beach vibes for an Insta-worthy vacationbrbrAdditional Information:brHouse Rules: No pets, smoking/vaping, or parties.brAge Requirement: Must be 21+ to rent and check in.brSecurity Deposit: А refundable hold at check-in, subject to inspection.brAmenities: Maintenance may occur; our team works promptly to resolve issues.brbrOn-site office hours:br8 am -4 pm Monday through Fridaybr9 am - 5 pm Saturday.

2BR Swap Frost for Blue Skies at Little Gull

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$362.36

Step onto the porch, take a deep breath, and let the salty sea air remind you—you’re officially on beach time. Whether it's a sunrise coffee or a sunset cocktail, the soft breeze and sound of waves set the scene for true relaxation on the Gulf.brbrThis Cape Cod-style 2-bedroom cottage offers old-school beach charm with thoughtful modern touches. It’s cozy, comfortable, and full of personality—perfect for couples, families, or small groups looking to slow down and soak up the Florida coast.brbrInside the Cottage:brPrimary Bedroombr• King bed for restful, breezy nightsbrbrLiving Roombr• Queen sleeper sofabr• Fireplace for a cozy touch on cooler eveningsbr• Smartly furnished with just the right beach vibebrbrKitchenbr• Galley-style, equipped with full-size appliances and all your essentialsbr• Ideal for whipping up snacks, simple meals, or your morning brewbrbrThe Resort Perks:br• Game room with pool table and ping pongbr• BBQ grills and shaded picnic areasbr• Complimentary bikes for island cruisingbr• Kid-friendly playgroundbrbrWildlife, Waves & Island WhimsybrLocated on Longboat Key, a laid-back island known for its natural beauty and vibrant wildlife. Keep your eyes out for gentle tortoises, graceful egrets, chattering parrots, and if you’re lucky, one of the island’s famous peacocks strutting by.brbrLittle Gull Cottage fits right in—charming, welcoming, and full of character.brbrKnow Before You Go:br• Stairs are required to access the cottagebr• No pets, no smoking, no vaping, no partiesbr• Must be 21+ to rent and check inbr• Refundable security hold due at check-in (subject to inspection)br• Occasionally, maintenance happens—but we handle it fast and hassle-freebrbrOffice Hours:br• Monday–Friday: 8 AM–4 PMbr• Saturday: 9 AM–5 PMbrbrIf you’re looking for a classic Florida beach experience with heart, soul, and a view worth the steps, Little Gull Cottage is waiting.

1BR Gulfside Cottage Charming, Quiet, and Warmer Than Your Forecast

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$378.97

Experience the charm of this cottage, featuring a generously sized main bedroom with a king bed, providing a comfortable and spacious retreat. Additional sleeping options are available with a queen sofa bed in the living room, offering flexibility for your accommodations. The living room is enhanced with a fireplace and ample seating, creating a cozy and inviting atmosphere. A well-equipped kitchen allows you to prepare a delightful morning coffee to savor on your porch, surrounded by the tranquility of the bay. brbrPlease note that a refundable security hold will be taken at the time of check-in. brbrImmerse yourself in the timeless Cape Cod style, as these cottages are adorned with fireplaces. Longboat Key's quintessential beach vibes are seamlessly woven into the surroundings, featuring a tiki hut, straw roofs, and brick-paved walkways for a picturesque setting. Fun for everyone is the promise, with total relaxation at the core of your vacation experience.brbrAdditional Information:brHouse Rules: No pets, smoking/vaping, or parties.brAge Requirement: Must be 21+ to rent and check in.brSecurity Deposit: А refundable hold at check-in, subject to inspection.brAmenities: Maintenance may occur; our team works promptly to resolve issues.brbrOn-site office hours:br8 am -4 pm Monday through Fridaybr9 am - 5 pm Saturday.

Your Winter Reset: Gulf Breezes + Good Vibes

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$374.22

Longboat Key is a haven for wildlife lovers, where you might spot tortoises, egrets, wild parrots, and even the island's famous peacocks. Little Gull Cottage blends seamlessly with the area's natural charm and style. This bayside cottage features a spacious main bedroom with a king bed and a private ensuite. The guest room includes two twin beds, and the living room offers additional sleeping space with a queen sofa bed. A shared hallway bathroom is conveniently located for all guests. The cozy living room, complete with a fireplace, is perfect for relaxing, while the well-equipped kitchen allows you to brew a fabulous morning coffee to enjoy on the porch.brbr**Stairs are required to access the cottage.brbrEmbrace the classic Cape Cod-style charm, with fireplaces and inviting beach vibes. brbrAdditional Information:brHouse Rules: No pets, smoking/vaping, or parties.brAge Requirement: Must be 21+ to rent and check in.brSecurity Deposit: А refundable hold at check-in, subject to inspection.brAmenities: Maintenance may occur; our team works promptly to resolve issues.brbrOn-site office hours:br8 am -4 pm Monday through Fridaybr9 am - 5 pm Saturday.

2BR Cottage Bayside of Property, Full Resort Amenities

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$344.56

Step back in time to the golden days of beach vacations—think breezy porches, tiki huts, and palm-fringed paths that lead straight to relaxation. Nestled in the heart of Longboat Key, this cheerful cottage combines retro charm with modern comforts for a truly memorable coastal escape.brbrYour private retreat is full of character and comfort, with a galley kitchen featuring full-sized appliances for easy meals and morning coffee rituals. The primary bedroom offers a king bed, while the cozy living room includes a queen sleeper sofa, creating space for up to four guests. A shared bath and beachy décor make it feel like home—only better.brbrEnjoy side and diagonal Gulf views right from your porch as you soak in the salty air and laid-back island vibe.brbrLongboat Key is alive with wildlife—tortoises, egrets, wild parrots, and if you’re lucky, one of the island’s famous peacocks might strut by. Little Gull Cottage fits right in, with its timeless style and natural surroundings.brbrPlease Note:brStairs are required to access this unitbrNo pets, no smoking or vaping, and no partiesbrMust be 21+ to rent and check inbrRefundable security hold due at check-inbrbrWhile we keep amenities in tip-top shape, maintenance may occur—and we strive to handle it swiftly.brbrOnsite Office Hours:brMonday–Friday: 8 AM – 4 PMbrSaturday: 9 AM – 5 PMbrbrReady to trade screen time for sunshine This cottage is the perfect blend of retro fun and modern-day comfort—just steps from the sand.

Throwback Charm Meets Beach Bliss 1BR Cottage

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$344.56

Step into a simpler time with this cozy Cape Cod-style cottage, where beach vacations feel timeless and the pace is set to relax. Located on the Gulf side of beautiful Longboat Key, this cottage offers a quiet coastal escape filled with old Florida charm.brbrWildlife lovers, take note: Tortoises, egrets, wild parrots, and even Longboat Key’s famous peacocks may wander by, adding a splash of nature to your stay.brbrEnjoy the resort’s classic beach ambiance, from tiki huts and straw roofs to brick-paved walkways that invite barefoot strolls. Whether you’re here to unwind or play, there’s something for everyone.brbrInside the Cottage:brPrimary bedroom with a king bedbrbrQueen sofa bed in the living roombrbrShared hallway bathroombrbrGalley kitchen with full-size appliances and essentialsbrbrCozy porch perfect for your morning coffee or evening winebrbrThis cottage comfortably hosts up to 4 guests. While it doesn’t offer a direct Gulf view, it’s just a short walk to the beach on the Gulf side of the property.brbrPlease note: Stairs are required to access this unit.brbrKnow Before You Go:brNo pets, no smoking or vaping, no partiesbrMust be 21+ to rent and check inbrRefundable security hold due at check-inbrbrWhile we aim for a seamless stay, maintenance may occur, and our team responds quickly.brbrOnsite Office Hours:brMonday–Friday: 8 AM – 4 PMbrSaturday: 9 AM – 5 PMbrbrThis is the kind of place where memories are made—slow mornings, sunny days, and peaceful nights by the sea. Welcome to Little Gull Cottage.

Salt Air, Sunlight, and Old Florida Flair

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$193.66

This Beachplace condo, situated on the sands of Longboat Key, Florida, offers a breathtaking, panoramic view of the Gulf of Mexico’s aquamarine waters! The 2-bed/2-bath direct oceanfront and RECENTLY UPDATED corner unit has new hurricane-impact glass doors and windows, new floorings throughout, completely renovated bathrooms, new custom closets, remodeled kitchen with new fingerprint-resistant stainless steel appliances, freshly painted walls, and new beach décor... brRelax inside, enjoying the soothing rhythm of the waves and the views of the glistening sunshine from the master bedroom, living room, and kitchen; Wine and dine on the wrap-around Lanai while admiring the sunset; Take a stroll along finely-combed, soft sands of the private beach, which is only steps away, and you might even catch dolphins dancing by... So, come enjoy this sensational paradise and an unforgettable getaway!br brBeachplace is a 24/7 gated and guarded community. It also features a luxurious club house with a fitness room, Club room, Olympic-sized heated swimming pool, children's pool, hot tub, Sauna, well-maintained tennis courts, pickle ball courts and a short drive to St. Armand’s Circle, where you can dine and wine at one of the many magnificent restaurants or shop for nifty items at those unique boutiques...br***RRCR#: RRR-00030.2023br***IMPORTANT:br1. Booking is by calendar month, exceptions may be made by the Owner.br2. Cancellation Policy varies depending on the Season and the duration of rental. PLEASE ASK OWNER for details!br3. Once reservation is made, Owner will provide a Lease, Welcome Guides, etc. br4. Condo Association has a No Pet, No Smoking Policy.

REMODELED!!! Enjoy a Taste of Paradise from an Oceanfront Condo on White Sands!

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$216.97

Welcome to this exquisite top-floor, 3 bedroom, 2 bath, end-unit condo at Bay Harbour by FVC. Newly furnished in 2022 and equipped with elevator access for your convenience. Start your mornings with a breathtaking view as you sip coffee overlooking the ocean, canal, and lush surroundings. Enjoy stunning vistas of the bay, meticulously landscaped grounds, and the inviting swimming pool.brbrAdventure awaits! Charter a yacht or pontoon or take a leisurely walk or ride to nearby restaurants and shops. Dive into paddleboarding, kayaking, swimming, golfing, or savor a home-cooked meal in a fully equipped kitchen. This exclusive island destination offers endless ways to relax and recharge, just a short causeway from the mainland.brbrInside, unwind with four new big-screen smart TVs, high-speed WiFi, a reclining leather sofa and bar area. The flexible bedroom with a Murphy bed doubles as a home office, perfect for combining work with a luxurious escape. BONUS, washer and dryer are conveniently located in-unit!brbrEach bedroom is designed with comfort in mind. The spacious king bedroom includes a daybed with two twin beds, while the queen master suite boasts an adjustable electric bed. Every room features private seating and a TV for maximum relaxation, whether you're traveling solo or with friends and family.brbrEnjoy the welcoming, safe, and upscale country-club atmosphere of Longboat Key. Spend your days lounging by the pool, exploring the neighborhood, and experiencing the beauty of ocean sunsets. From fresh ocean air to world-class dining, friendly locals, and boutique shopping, this destination has it all.brbrMake the most of your evenings with a two-minute stroll to Dockside Restaurant. Savor gourmet cuisine and cocktails on the water, all while watching a spectacular sunset. Whatever you desire, you’ll find a magical experience waiting for you in this luxurious Longboat Key condo!brbrLongboat Key RRR-01213.2024

Bay Harbour A306 by FVC

Longboat Key, Florida, United States

3

Bed

Bath

Sleeps

$381.69

Experience resort-style living in this beautifully updated sixth-floor condo at Promenade. The expansive open floor plan connects a modern kitchen to a spacious great room, leading to a large terrace with breathtaking ocean and bay views and unforgettable sunsets.brbrEnjoy exclusive access to 400 feet of private beachfront, a fully equipped fitness center, oversized heated pool and spa, private boardwalk to pristine white sands, and on-site management for added convenience. Just minutes from the shops and restaurants of St. Armands Circle.brbrRental requires a minimum stay of 3 consecutive months, making it perfect for seasonal getaways and long-term relaxation.

Luxury Coastal Escape in Longboat Key, Florida-Beachfront Condo for Rent!

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$543.12

Experience the Ultimate Getaway at Our Brand New Villa on Longboat Key!brNO HURRICANE DAMAGE!!!brbrEscape to paradise in our stunning brand new villa on Longboat Key, where luxury meets comfort! This exquisite retreat features two beautifully appointed bedrooms, including a master suite with a king-sized bed, a walk-in closet, and a private bathroom complete with a relaxing tub overlooking the tranquil canal. The second bedroom offers a cozy queen-sized bed and its own private bathroom, making it perfect for families or friends.brbrIndulge in the spacious living and dining area, or whip up a delicious meal in the fully equipped kitchen. Step outside to our beautiful porch, featuring a dining area and a lounge space with an outdoor kitchen—ideal for al fresco dining under the stars!brbrBring your boat and dock it right by the house, surrounded by a beautifully landscaped garden and private parking. Enjoy ultimate privacy with stunning canal views, and catch a glimpse of the gorgeous Gulf of Mexico from the hallway.brbrOur villa is equipped with high-end finishes, a washer/dryer, ample storage, and all the essentials you need for a perfect stay. We provide linens, towels, beach chairs, umbrellas, and games for both kids and adults. Plus, upon request, we can arrange kayaks for an additional fee.brbrUnwind in the outdoor living space by the newly built large heated pool, shared with the other unit on the property. With two gates and separate areas for entering the water, there’s plenty of room to relax and soak up the sun. Lounge chairs and umbrellas are provided for your comfort. (Please note: Pool heating is available for a charge.brbrDuring your stay, enjoy the delightful company of our resident manatees, who love to visit the Boathouse!brbrLongboat Key offers pristine beaches with limited public access, ensuring a peaceful retreat. The closest public beach access is at 6399 Gulfside Road, with parking available at General Harris Street. Please remember to use only public beach access points.brbrYour safety and security are our top priorities. Our property is equipped with RING and NEST surveillance devices for your peace of mind.brbrDon’t miss out on the best dining options in Sarasota! brCheck out this link for the top restaurants: Best Restaurants in Sarasota (https://www.sarasotamagazine.com/eat-and-drink/best-restaurants-sarasota utm_campaign=Newsletter%20-%20SAR%20Biz%20Daily&utm_medium=email&_hsmi=107418908&_hsenc=p2ANqtz-86vaCriuyscrrDtMB-bvHWnb3LerJSx9FnIDAW6kjLUfzU-Grgk0xemQgEsI_zvJ_h0LdjHUZ1XUlCF1480v5tN5Uf1Q&utm_content=107418908&utm_source=hs_email).brbrBook your unforgettable vacation today! We can’t wait to welcome you to your dream home away from home on Longboat Key!

Villa

Stunning Modern Villa with Private Pool&Dock on Longboat Key.Your Dream Getaway!

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$400.21

Newly Renovated!! Sunny southern exposure abounds from this charming 2 bedroom 2 bath get a way at Beachplace. This third floor residence has wonderful Gulf beach views from the balcony. It is tastefully furnished with a spacious split bedroom plan. Flat screen TVs in the living room and both bedrooms, DVD players and wireless internet all for your enjoyment. The master bath, has a rain shower head and bench for seating. The spare bathroom, has a bath tub/shower combo. The kitchen includes a 36 inch induction range, and is fully stocked with all your cooking needs. Tropical landscaping and peaceful setting make it hard to ever leave. Beachplace, located on a prime stretch of perfect sandy beach of the Gulf, offers residents first-rate amenities. Heated pool and spa, stylish clubhouse, fitness center, and just steps to the beach and the pool. Close to the renowned shops and world-class dining at St. Armand's Circle and downtown Sarasota. One premium under-building parking space is included.

Relaxing Beachside Retreat on Longboat Key

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$404.87

Exclusive Gulf View Condo – Sand Cay Beach Resort, Unit 206, Longboat Key brbrWelcome to Longboat Key, one of the most beautiful and exclusive islands in Florida – ranked as the 2nd most favored island in North America by a leading travel magazine. Here, the authentic Florida beach lifestyle blends seamlessly with an elegant, upscale environment: miles of soft white sand, turquoise waters, refined dining, boutique shopping, and the tranquility of island life.br brAt the heart of the island lies the Sand Cay Beach Resort, a boutique beachfront property with just 60 privately owned condominiums. With its direct beach access, tropical gardens, heated pool, tennis & pickleball courts, BBQs, and on-site office, the resort combines relaxed Floridian charm with the comfort of a well-managed community.brbrbr✨ Condo Highlights – Unit 206 (Gulf View Category)brbr• 2nd floor condo with elevator access – perfect vantage point with panoramic Gulf views and unforgettable sunsetsbr• Fully renovated & modernized – updated bathrooms, hardwood floors, fresh paint, Caribbean-inspired décorbr• Premium equipment: 2024 Samsung Smart TV, BOSE Bluetooth sound system, Royal Doulton dishes, Villeroy & Boch kitchen accessoriesbr• Spacious 2BR / 2BA layout – ideal for families or couples traveling togetherbr• South-facing orientation – natural light fills the condo all daybrbrbr ️ Everything You Need for the BeachbrbrTo make your beach days effortless, we provide:br• Tommy Bahama portable beach chairsbr• Towelsbr• Umbrellasbr• Coolers for cold drinks and snacksbrbrbr☀️ Living & Comfortbrbr• Beach Style Interior: Bright, airy design with hand-picked furniture, coastal artwork, and stylish accessories that create an authentic Floridian atmosphere. Every detail, from the colors to the décor, reflects the charm of the Gulf Coast and makes you feel instantly at home.br• Fully equipped kitchen: Stainless steel appliances, ice cube maker, dishwasher, and a complete set of high-quality cookware, dishes, and utensils for every needbr• Open floor plan with kitchen, dining, and living areabr• DirecTV with a wide selection of live channels, including major sports networks – perfect for catching your favorite football games, movies, or family shows during your stay.br• High-Speed WiFi (up to 500 Mbit) – reliable and fast internet connection, perfect for streaming, video calls, and remote work.br• High-End hardwood flooring throughout for a fresh and elegant lookbrbrEverything you need for family meals, relaxed breakfasts while overlooking the ocean, or sunset dinners is at your fingertips.brbrbr Resort Amenities (included)brbr• Heated pool year-roundbr• Tennis & pickleball courts, shuffleboardbr• Beach furniture & loungers provided right on the sandbr• BBQ area directly at the beach – grill with a breathtaking ocean viewbr• Free WiFi across the resortbr• Complimentary laundry facilitiesbr• On-site office with friendly staff ready to assistbrbrbr Beaches & LocationbrbrFrom Unit 206, you are just steps from the white sandy beach of the Gulf of Mexico – semi-private, quiet, and never overcrowded. Watch pelicans, dolphins, and unforgettable sunsets right from your condo or while enjoying a stroll along the shore.brbrNearby you’ll also find:brbr• St. Armands Circle – fine dining & boutique shoppingbr• Robinson Preserve & Myakka River State Park – kayaking, bird watching, and Florida wildlifebr• Sarasota & Tampa Bay – culture, aquariums, theme parks, and morebrbrbr AtmospherebrbrBegin your mornings on the patio with the sound of the waves and the warmth of the Florida sun. Spend the day on the beach or by the pool, and in the evening relax with a glass of wine as the sky turns pink and orange. Fire up the beachside BBQs and grill with one of the best views on Longboat Key – the Gulf of Mexico right in front of you.brbrbrBook your stay at Sand Cay Beach Resort, Unit 206 (Gulf View Category), today and experience the perfect mix of authentic Floridian beach life and the luxury of Longboat Key’s exclusive island setting.

Exclusive Beach-Style Condo with great Gulf-View Sand Cay 206, Longboat Key

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$319.77

Welcome to Lyons Lane, a beautiful canal-front Longboat Key vacation rental offering the perfect blend of privacy, comfort, and coastal living. Proudly presented by RVA, this spacious two-story home is located on the quiet north end of Longboat Key, directly across from protected wetlands that provide peaceful scenery, abundant wildlife, and a true island escape.brWhether you're planning a seasonal stay, extended vacation, or relaxing snowbird retreat, this pet-friendly Longboat Key rental with a private pool and boat dock delivers everything you need for an unforgettable Florida Gulf Coast experience.brbrPrivate Pool, Hot Tub & Waterfront Outdoor Living - Designed for outdoor relaxation, this waterfront Longboat Key vacation home features a private heated swimming pool, separate hot tub, and a large screened-in deck overlooking a tranquil saltwater canal. Enjoy morning coffee by the water, afternoons lounging poolside, and beautiful Gulf Coast sunsets in your own private backyard oasis.brbrBoating enthusiasts will appreciate the private boat dock, providing convenient water access to Sarasota Bay and surrounding waterways—perfect for fishing, kayaking, paddleboarding, or simply enjoying life on the water.brbrOutdoor Highlights:br• Private heated pool br• Separate hot tub br• Canal-front screened lanai and sun deck br• Private boat dock br• Gas grill for outdoor dining br• Peaceful waterfront setting br• 2-car garage and ample parking brbrThis waterfront Longboat Key vacation rental is ideal for guests seeking a relaxing coastal lifestyle during their monthly stay.brbrSpacious 4-Bedroom Home Perfect for Families and Monthly StaysbrWith four bedrooms and two bathrooms, this 1,718-square-foot Longboat Key vacation home comfortably accommodates up to eight guests. The open-concept layout and split-bedroom design provide both gathering space and privacy, making it an excellent choice for families, remote workers, retirees, or seasonal visitors.brThe fully equipped kitchen includes stainless steel appliances, a natural gas cooktop, double electric oven, and everything needed to prepare meals at home after a day at the beach or exploring the island.brbrInterior Features:br• Open-concept living and dining area br• Fully equipped kitchen with stainless steel appliances br• Natural gas cooktop and double oven br• Comfortable coastal furnishings br• 60 flat-screen TV in living room br• High-speed Wi-Fi br• Full-size washer and dryer br• Spacious split-bedroom floor planbr brThis Longboat Key monthly rental is especially well-suited for extended stays, snowbirds, and guests seeking the comfort of a true home-away-from-home.brbrWalk to Beach, Bay, Restaurants & Local AttractionsbrLyons Lane offers the convenience of a walkable Longboat Key location, just a short stroll to the Gulf Beaches and nearby bay access. Enjoy easy access to local restaurants, boutique shopping, marinas, and outdoor recreation while still enjoying the peace and quiet of a residential neighborhood.brbrPet-Friendly Longboat Key Vacation RentalbrTraveling with pets is easy at Lyons Lane. This pet-friendly Longboat Key rental welcomes your furry family members so everyone can enjoy the vacation together.brbrPet Policy:br• Pets allowed with approval br• 50 lb weight limit br• Additional pet fee applies brbrProperty DetailsbrAccommodations: 4 Bedrooms | 2 BathroomsbrSleeps: Up to 8 GuestsbrBeds: 1 King | 3 Queen BedsbrView: Canal Front / WaterfrontbrMinimum Stay: 30 DaysbrbrAmenitiesbrPrivate Heated Pool • Hot Tub • Canal Front • Private Boat Dock • Screened Lanai • Gas Grill • Washer/Dryer • High-Speed Wi-Fi • 2-Car Garage • Full Kitchen • Pet Friendly • Walk to Beach • Monthly RentalbrbrImportant Notesbr• Dock available for recreational use br• Additional electric and/or pool heating charges may apply br• Minimum 30-day stay required br• Pet approval required prior to arrival

Private Vacation Home

Luxury Canal-Front Rental on Longboat Key | Pool, Dock & Lift

Longboat Key, Florida, United States

Bed

Bath

8

Sleeps

$399.22

Escape to this charming bayside cottage, featuring a spacious main bedroom with a king bed and a living room with a fireplace and queen sofa bed for extra sleeping space. The well-equipped kitchen is perfect for preparing your morning coffee, which you can enjoy on the porch, soaking in the serene bay views.brbrEmbrace the resort's timeless Cape Cod-style charm, where tiki huts, straw roofs, and brick-paved walkways create the perfect beachside setting. Longboat Key's vibrant wildlife—tortoises, egrets, wild parrots, and even famous peacocks—adds to the charm of your stay.brbrAdditional Information:brHouse Rules: No pets, smoking/vaping, or parties.brAge Requirement: Must be 21+ to rent and check in.brSecurity Deposit: А refundable hold at check-in, subject to inspection.brAmenities: Maintenance may occur; our team works promptly to resolve issues.brbrOn-site office hours:br8 am -4 pm Monday through Fridaybr9 am - 5 pm Saturday.

Relax and Recharge in this 1BR Cottage

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$599.66

Looking to relive the beach vacations of your childhood—minus the car fights and soggy bread Welcome to your grown-up version of yesteryear fun. This charming 2-bedroom cottage blends old-school beach bliss with the comfort and convenience today’s family travelers crave.brbrStep inside to a spacious king bedroom with a private ensuite—perfect for parents who need their own space. The guest room has a cozy queen bed, and the living room’s queen sofa gives the kids their own sleepover setup. A shared hallway bathroom keeps things convenient, and the galley kitchen (yes, full-sized everything) means you can actually cook real meals—or reheat leftovers from that seafood shack down the road.brbrPlease note, while the cottage is located on the Gulf side, it is not directly Gulf-frontbrbrBeach nostalgia, but better. Think: tiki huts, swaying palms, and brick walkways that make you feel like you’ve stumbled into an old postcard. brbrImportant to know: This unit does require stairs.brbrThe Fine Print:brHouse Rules: No pets, smoking, vaping, or partiesbrAge Requirement: Must be 21+ to rent and check inbrSecurity Deposit: Refundable hold at check-in, pending inspectionbrbrAmenities: Maintenance may occur; our team works promptly to resolve issues.

2BR Cottage Gulf Side of Property, Resort Amenities

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$604.4

Situated bayside with breathtaking views, this four-bedroom cottage is the ideal spot for your Florida beach getaway. The main bedroom has a king-sized bed and a private ensuite, while the first guest room offers a queen-sized bed. The remaining two bedrooms each feature two twin beds, and a queen-sized sleeper sofa in the living room provides additional sleeping space. The second bathroom is shared with the common area. The spacious living room, adorned with a tiled fireplace, offers ample seating. The well-equipped kitchen has everything you need for a great meal. All you have to bring are your groceries. brbrPlease note that a refundable security hold will be taken at the time of check-in, and access to the cottage requires walking up steps.brbrIndulge in the charming atmosphere with features like a tiki hut, straw roofs, and brick-paved walkways. The promise of fun for everyone is complemented by the central theme of total relaxation, ensuring a memorable vacation experience.brbrAdditional Information:brHouse Rules: No pets, smoking/vaping, or parties.brAge Requirement: Must be 21+ to rent and check in.brSecurity Deposit: А refundable hold at check-in, subject to inspection.brAmenities: Maintenance may occur; our team works promptly to resolve issues.brbrOn-site office hours:br8 am -4 pm Monday through Fridaybr9 am - 5 pm Saturday.

Your Home Away from Home: Little Gull 4BR Cottage

Longboat Key, Florida, United States

Bed