Home Vacation Home Rentals By Owner In Longboat Key, FL

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Exceptional(10)

$380.7

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Private Vacation Home

Updated Townhome, Secluded Beach + Pool

Longboat Key, Florida, United States

Renovation completed in 2025! New master bath, whole house repaint, new furniture, etc. Longboat Key beach is ok post-hurricane, stores and restaurants open! Private updated townhome, just 100 yards from the beach. The spacious 2BR/2.5BA new listing has been tastefully furnished. It is within the exclusive community of Cedars East which offers a pool, fitness center, tennis, kayak/paddleboard launch and private fishing pier.brbrThe home is situated on a quiet cul-de-sac abutting mangroves, creating privacy throughout. It is within the exclusive community of Cedars East which offers a pool, fitness center, tennis, kayak/paddleboard launch and private fishing pier with plenty of seating including a picnic table and umbrella. Being near the front of the property makes beach access a breeze! You are sure to have an enjoyable vacation whether spending time at the beach, reading on the lanai, fishing, swimming in the pool, or exploring the shopping and restaurants in the area.brbrTwo bedrooms are located upstairs, each with their own private bathroom. The master bedroom features a king bed with custom closet and flat screen TV. The attached newly renovated bathroom offers a stand up shower and new dual-vanity sink.brbrThe main level features a fully stocked and recently renovated kitchen, half bath, dining room, screened in lanai, living room with two sofas (one pulls out into a full-size bed), and television.brbrThe second bedroom offers a queen bed with pull out trundle bed. The updated hall bathroom features a stand up shower and large vanity.brbrThe recently refinished garage offers a small grill and all the beach essentials including chairs, beach cart, cooler, and beach toys. Bikes are available from Cedars (for an additional fee) or from a vendor nearby.brbr*Children are welcome, please note there are two sets of stairsbr*Small dogs (under 30 pounds) - two - are allowed with prior approval and pet fee.br*Non-smokers pleasebr*contact me for shorter or longer stays br*The home can sleep 6 but there could be an additional $75 laundry fee for stays with more than 4 guests which goes directly to the cleaning servicebrbrWith all rentals, you have access to the community pool, kayak launch, nature trails, and fishing pier. For an added fee you can gain access to the tennis resort and fitness center as well. Fees are as follows, payable directly to the clubhouse:brbrFitness Center + Access to Bikes br-$90 one person/$150 familybrbrTennis Alone (does not include Fitness) br- $160 one person/$300 couple - Oct to Aprilbr- $45 one person/$60 couple - May to SeptbrbrGuest accessbrYou can enjoy the area on foot, on bike, or by car. There is a walking path throughout the community that will take you to the amenities. There is a walking/bike path along Gulf of Mexico Drive and Joan M Durante community park with trails is also nearby.brbrOther things to note:brPlease reach out before booking with pets.
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Exceptional(11)

$511.98

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Condo

Beachcomber unit 506

Longboat Key, Florida, United States

Enjoy breathtaking sunsets from this fifth floor Gulf front condo on the beach with full ocean views from every room. The living and dining rooms, decorated in Florida contemporary style, and the two bathrooms are all recently remodeled. br br The living room has a 55 smart TV. The master bedroom with its en suite bath and the living room each have sliding glass doors that open onto a 34 foot balcony overlooking the pool, beach, and the blue Gulf waters.br The balcony has a glass-paneled railing to allow uninterrupted views of the ocean from the interior. The master bedroom has a tropical flair, the second bedroom has a nautical decor, and the fully-equipped kitchen,, has stainless steel appliances and granite countertops. To add to the relaxing atmosphere, ceiling fans provide a gentle breeze in each room.br br On behalf of our guests and owners that suffer from asthma and allergies, no pets are allowed on the property. No exceptions! $300 fine.br br Please note: We do not allow Sunday or holiday arrivals and require a 7 night minimum stay.br br Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance.br Amenities Include:br - Balcony: Yesbr - Bed Size 1st/Master: Kingbr - Bed Size 2nd Rm: Queenbr - Beds Pull-out: 0br - Ceiling Fans: bdrms/liv. rmbr - Internet Access: Yesbr - Micro/Dishwash/Disp.: Yesbr - Refrig And Ice Maker: Yesbr - Square Footage, Est.: approx. 900 sq. feetbr - TV Cable/Satellite: Cablebr - TVs/VCR/DVD: 3/0/0br - View: Gulfbr - washer dryer: on propertybr - Max number of People: 4br - Hair dryer: Yesbr - Bathtub/Shower: Yesbr - Gulf view: Yesbr - Beach view: Yesbr - Beach front building: Yes
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$278.5

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Condo

No Longer Available! Spacious 2-BR/2 Bath Condo at Seaplace in Longboat Key, FL

Longboat Key, Florida, United States

3 month minimum staybrbrSpacious (1257 sqft), 2nd floor, non-smoking, 2 bedroom/2 bathroom condo with screened lanai. The Condo Association does not allow pets.brbrFull size custom kitchen and appliances with granite countertops and plenty of storage. Comes furnished with pots, pans, bakeware, dishes, silverware, glassware, coffee maker, toaster, blender. Pass-through to dining room with bar-top.brbrGenerous-sized master bedroom with king-size bed, walk-in closet, desk nook and sitting area with TV. Second bedroom has 2 twin beds and mattress topper to convert to king. Sleeper sofa in living room. Towels and linens provided.brbrMaster ensuite bath has walk-in shower and double sinks. Guest bath has tub/shower and double sinks.brbrCable TV, private wifi and utilities included. brbrMaximum occupancy: 6brbrSeaplace is a gated, vibrant, active community with lots of amenities, including 2 swimming pools, 2 tennis courts, clubhouse, fitness room, 1/2 mile of gulf beach front, and a walking path around the property. The events committee makes sure there is plenty to do with movie night, game night, food trucks, and water aerobics. Check out the website for property photos and activities! https://engage.goenumerate.com/site/2669/home.phpbrbrMinimum stay: 3 months - January, February, March - $21,000 plus state and county taxesbrOption to add December at $5000br$120 application/parking decal fee payable to Seaplace AssociationbrExact dates flexible
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$351.97

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Condo

Sutton Place #102A Condo by RVA

Longboat Key, Florida, United States

Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street. Available for monthly rental.brbrbrbrLimited Membership Privileges: Guests of Sutton Place #102A will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Two-bedroom, two-bathbrbrbrbrAmenities: Full-size Kitchen, 2 Community Pools, Fishing Pier, Game Room, Fitness Center, Clubhouse, Wireless Internet Access, Washer/Dryer, Community GrillbrbrbrbrLocation: 605 Sutton Place, Longboat KeybrbrbrbrBedding: 1 King, Queen Murphy BedbrbrbrbrView: Bay Front ViewbrbrbrbrMinimum Night Requirements: 1 monthbrbrbrbrAssociation Requirements: $100 Application Fee + $25 to Lighthouse Property Processing Fee + 10-Day Approval Time
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$1,747

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Private Vacation Home

AVAILABLE February 2027! 3 minute walk to the beautiful white quartz sand.

Longboat Key, Florida, United States

Embrace yourself with pure luxury and privacy, surrounded by lush landscaping and steps from the gorgeous Gulf of Mexico waters! This vacation home is over 4,300 square feet and is perfect for families and executive retreats providing flexibility and privacy for all guests. * 8 adults maximum and 2 kiddo's. Sleeps 10.br4 of the 6 bedrooms have an en-suite. 4 bedrooms with King beds. This home provides multiple areas to collaborate and make memories that will last a lifetime. Bring the entire family for the perfect beach getaway! brbrA one minute stroll to the private white beach of Longboat Key! The home is fully equipped with all kitchen appliances, cutlery and basic cooking accessories. There are 3 levels of outdoor living/lounging decks for you to enjoy. Each level provides a different experience. The top level provides a tranquil and quiet area for you to enjoy the 360 views of the intercostal and the Gulf. The second level offers a high end BBQ station with seating for 10 guests which offers a great place to mingle and enjoy each other's company. The ground level provides many offerings to every age. You will be embraced with lush landscaping that provides a tropical oasis. The backyard features a gorgeous pool, with sun shelf, waterfalls and a spa. It also provides multiple seating areas for you and your guests to enjoy.brbrYour dog will love the backyard as there is room to run and they are safe within the property with a 6 foot privacy fence with locking gates.brbrWhen you are ready to venture off property, and head to the beach, we have you covered. In our fully equipped garage, you will find everything you need for the beach (umbrellas, chairs, towels, wagon, paddle boards). Provided on property for your enjoyment are 2 adults bikes and 2 children bikes. With being centrally located, there is a 15 mile walking path, north to south for you to explore. brbrAnd if you are still looking for something to do, there is a ping pong table and a putting green in the backyard.brbrWe welcome you as a guest and we strive to ensure that your experience is carefree and easy so you can enjoy the luxuries of our beautiful island home. The house is situated on a private drive and perfectly located for you to be able to walk to the beach, restaurants and parks. And when you are ready to venture to the city, it's a short drive to the many activities offered in Sarasota (10-15 mins), Anna Maria Island (15 mins), St. Armand's Circle (10 mins), Lido Key Beaches (15 mins) to name a few.brbr2 dogs maximum allowed 40 lbs or less $250.00 non refundable pet fee per pet at time of reserving. The Host MUST approve all dogs prior to booking.brbrInterim clean is required every 2 weeks at the expense of the Guest. $525.00 per interim clean.brbrNOTE: Due to Longboat Key Rental laws, the minimum stay for any rental in the area is 30 days.brbr*Security Cameras located at front door, Driveway, side of house over pool equipment.
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Exceptional(82)

$340.91

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Condo

Wonderful Canal Front Condo on LBK! Bring Your Boat!Cabana Beach Club UNIT 11.

Longboat Key, Florida, United States

Welcome to Unit 11 at Cabana Beach Club, a beautiful and comfortable one-bedroom waterfront retreat with stunning bay views and a private dock, perfect for guests who want to bring their own boat. With a bedroom plus a living room sleeper sofa, this unit comfortably accommodates up to four guests.brbrCabana Beach Club is a quiet, boutique complex with only 11 units, offering exceptional privacy and a relaxed coastal atmosphere. The canal-side section consists of just three units, making this an ideal setting for a peaceful waterfront getaway.brbrThe Gulf of Mexico’s pristine beaches are directly across the street—just a short walk away. Guests also enjoy access to a community heated pool, conveniently located nearby.brbrInside, the unit is fully equipped with everything you need for a carefree stay, including a stocked kitchen with utensils, silverware, pots and pans, fresh towels and linens, and beach chairs. Additional comforts include smart TVs in both the living room and bedroom and a washer and dryer inside the unit.brbrA convenience store is within walking distance, and you’ll find excellent restaurants nearby, with even more dining, shopping, and entertainment just a short drive away in Sarasota.brbrTraveling with family or friends We own all three canal-side units—ask about Units 10 and 12 when planning a group or family stay.
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$303.64

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Condo

Tiffany Plaza in Longboat Key, FL

Longboat Key, Florida, United States

Longboat Key Gulf Front Vacation Rental! Enjoy fabulous views from almost every window in this 2 bed, 2 bath condo on the Key! Relax to the sound of the waves as you watch fabulous sunsets in this amazing waterfront community. This wonderful property features a King bed in the primary suite with a walk-in closet, bath with dual sinks and spacious shower. The guest bedroom has Queen sleeping accomodations a a lovely guest bath. The kitchen has been updated and has a bonus room which can be used as an office or last minute guest room as it offers a horizontal twin Murphy bed. The living/dining room overlooks the Gulf of Mexico, and the open patio invites you! This small, intimate community offers a sparkling heated pool and a private beach for your enjoyment. You have one covered parking space and plenty of guest spaces. This well managed complex offers a club room and sauna in addition to on-site management! Welcome to paradise!brbrFor more information contact Stephanie Deshales at 941 780--3229 or by email to brbrInformation contained herein deemed reliable but not guaranteed.brbrAmenities Include:brbr- Bldg. Complex Name: Tiffany Plazabrbr- Type Unit: Low Rise Condobrbr- Unit Rating: goldbrbr- Beach Access Type: Beachfrontbrbr- Elevator: Yesbrbr- Floor/Bldg Height: 2/6brbr- Year Built: 1975brbr- Approx. Sq. Ft.: 1411brbr- Exposure/View: Westbrbr- Pool/Spa: yes communitybrbr- washer dryer: Yesbrbr- Parking Type: 1 carportbrbr- Lanai / Balcony: openbrbr- Bbq Grill: Yes communitybrbr- Master Bedroom: Kingbrbr- Bathrooms-Master: Shower onlybrbr- Guest Bedroom: Queenbrbr- Bathrooms-Guest: Tub/showerbrbr- Den- Desk / Pull Out: Desk/horizontalbrbr- Flooring: Tilebrbr- TV/Dvd/ Stereo: 2brbr- Internet Access: Wifibrbr- Listing Advisor: Stephanie Deshaiesbrbr- Min. Rental # x perYr: 30x12brbr- Security Deposit: 1500brbr- Reservation Fee: $170brbr- Damage Protection: $60brbr- Application Fee Req.: $150brbr- Departure Clean Fee: $200brbr- Taxes: 12%brbr- Utility Charges: $100 off seasonbrbr- Other: $1,000 common area depositbrbr- Rate - Monthly: $10,000/$5900brbr
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Exceptional(1)

$477.6

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Private Vacation Home

Aqua Bay 3BR by RVA-Poolside Luxury, Pets Too

Longboat Key, Florida, United States

Aqua Bay in Longboat KeybrbrModern Key West Luxury | Walk to Beach | Monthly Longboat Key Vacation RentalbrbrWelcome to Aqua Bay, a stunning coastal retreat in the exclusive Conrad Beach community on North Longboat Key. Professionally managed by RVA Vacation Rentals, this beautifully maintained Key West–style home blends modern elegance, resort-style amenities, and peaceful coastal living—all just a short stroll to the world-famous sugar-white beaches of the Gulf of Mexico.brbrPerfect for snowbirds, seasonal residents, relocation stays, remote workers, and extended beach vacations, this spacious monthly rental offers privacy, comfort, and an unbeatable location between Anna Maria Island and St. Armands Circle.brbrWhether you're seeking a relaxing winter retreat, a long-term coastal escape, or a luxury furnished monthly rental in Longboat Key, Aqua Bay delivers the ideal blend of comfort, style, and convenience.brbrProperty Overview:br3 Bedrooms | 3 Bathrooms | Sleeps 6brMonthly Vacation Rental on Longboat KeybrPet-Friendly (Pets Considered)brShort Walk to BeachbrCommunity Pool AccessbrProfessionally Managed by RVA Vacation RentalsbrbrAddress: 7030 Firehouse Rd, Longboat Key, FloridabrbrBedding Configuration:br• Primary Suite: King Bedbr• Guest Bedroom: Queen Bedbr• Guest Bedroom: Two Twin Bedsbr• Coastal Elegance Meets Everyday ComfortbrbrStep inside this beautifully designed Key West-inspired vacation home, where bright interiors, coastal décor, and open-concept living create an inviting space for relaxation and connection. Expansive windows fill the home with natural light while capturing refreshing Gulf breezes that define the laid-back luxury of Longboat Key living.brbrThe spacious living and dining areas are perfect for entertaining guests, hosting family dinners, or simply unwinding after a day at the beach.brbrThe fully equipped chef’s kitchen features:br• Large center island with seatingbr• Modern appliancesbr• Ample counter spacebr• Open layout ideal for entertainingbr• Perfect setup for extended stays and monthly rentalsbrbrUpstairs, private bedroom suites provide peaceful retreats for rest and relaxation, including a tranquil primary suite designed for comfort and privacy during long-term stays.brbrOutdoor Living & Resort-Style AmenitiesbrbrOne of the most desirable features of Aqua Bay is its multiple outdoor living spaces. Each level offers a private deck or terrace, creating the perfect setting for:br• Morning coffee with ocean breezesbr• Afternoon reading in the sunbr• Evening cocktails at sunsetbr• Relaxing outdoor diningbrbrGuests also enjoy access to the Conrad Beach community pool, just steps from the home—ideal for cooling off after a day at the beach.brbrAdditional Amenities Include:br• Multiple private sun decks on all levelsbr• Short walk to Gulf of Mexico beach accessbr• 1-car garage with additional storagebr• High-speed Wi-Fi for remote workbr• Washer and dryerbr• Walk-in closetsbr• Central air conditioningbr• Quiet residential neighborhoodbr• Ideal for monthly and seasonal staysbr• Prime North Longboat Key Locationbr• Free On site parkingbrbrAqua Bay is perfectly positioned on the quiet north end of Longboat Key—one of Florida’s most desirable coastal destinations. This location offers the perfect balance of tranquility and accessibility to nearby attractions.brbrEnjoy easy access to:br• Gulf of Mexico beaches for swimming and shellingbr• Sarasota Bay for fishing and kayakingbr• Anna Maria Island shopping and diningbr• St. Armands Circle boutiques and restaurantsbr• Championship golf coursesbr• Scenic bike paths along Longboat KeybrbrThis property is especially popular with:br• Snowbirdsbr• Seasonal rentersbr• Remote workersbr• Relocating professionalsbr• Extended vacation guestsbr• Couples and families seeking a peaceful coastal lifestybrbrWhy Guests Love Aqua Baybrbr✔ Walk to Beach in Minutesbr✔ Quiet, Upscale Communitybr✔ Multiple Outdoor Decksbr✔ Monthly Rental Ideal for Snowbirdsbr✔ Pet-Friendly Optionbr✔ Spacious Layout with Private Suitesbr✔ Prime North Longboat Key Locationbr✔ Professionally Managed by RVA Vacation Rentalsbr✔ Perfect for Extended Stays and Seasonal RentalsbrbrMonthly Rental DetailsbrbrMinimum Stay: MonthlybrPets: Considered with approvalbrAssociation Requirement: $250 Application FeebrOccupancy: Up to 6 Guests
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Exceptional(3)

$399.39

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Completely Renovated, Brand New Furnishings, Beach Castle 21

Longboat Key, Florida, United States

Welcome to your dream getaway at Beach Castle Resort Unit 21! This fully renovated and newly furnished ground-floor beach condo offers the perfect blend of modern amenities and coastal comfort. With fresh updates and new photos coming soon, this two-bedroom, two-bath condo is designed for relaxation and style.brbrThe open living space features a serene coastal vibe with plush furnishings and SMART TVs, making it ideal for unwinding after a day at the beach. The spacious primary bedroom boasts a luxurious king bed, while the guest bedroom is thoughtfully appointed with two cozy queen beds. A queen sleeper sofa adds extra sleeping space for larger groups.brbrThe all-new kitchen is equipped with state-of-the-art appliances, perfect for preparing delicious meals. Enjoy the convenience of private beach access and a short stroll to both the serene Bay and the sparkling Gulf of Mexico. Beach essentials are provided, so you’re ready for sun-soaked days by the water.brbrWhether you’re here to relax on the sand or explore the area’s natural beauty, this condo promises an unforgettable vacation experience. Book now to be among the first to enjoy this stunning renovation!brbrAbout Beach Castle ResortbrEscape to the timeless allure of Beach Castle Resort, a family-friendly community nestled on picturesque Longboat Key, offering an enchanting blend of Old Florida charm and modern comfort. The resort boasts a range of accommodation options, including 1 and 2 bedroom condos, each meticulously designed to provide a cozy and inviting atmosphere for your stay.brbrImmerse yourself in the essence of relaxation at our community heated pool and hot tub, surrounded by comfortable chairs, umbrellas, and tables, perfect for unwinding under the warm Florida sun. For the active traveler, we offer tennis and pickleball courts to indulge your competitive spirit.brbrIf you're a fishing enthusiast, our private boat dock with a convenient fishing table awaits your catch of the day. Savor the outdoors with a bayside gas grill, ideal for cookouts, and enjoy your meals at the adjacent table and chairs.brbrExploration is at your doorstep, with a leisurely stroll to nearby restaurants and shops. And when you're ready for some beachfront bliss, our private beach access welcomes you with sun loungers, umbrellas, and a beachside patio featuring a table, chairs, and a gas grill for seaside picnics. Rinse off the salt and sand in our outdoor shower after a day in the waves.brbrAt Beach Castle Resort, you have the flexibility to enjoy a short getaway or an extended stay, making it one of the rare resorts that cater to your vacation preferences. Discover a tranquil haven where memories are made and cherished amidst the beauty of Longboat Key's coastline.brbrLongboat Key Life brLongboat 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.brbr**IMPORTANT PARKING INFORMATION**brBeach Castle Resort has a new parking pass policy in place. Each reservation includes one on-site parking pass, which must be clearly displayed on your dashboard whenever your vehicle is parked on the property. You’ll find the pass inside the condo—please retrieve it after check-in time. To avoid any issues, we kindly ask that you do not park at the resort before check-in or without the pass displayed. Unauthorized vehicles may be towed. An extra parking pass will be provided for The Cedars Condominiums just a short distance up the street. Thank you for your cooperation and understanding!brbrTown of Longboat Key: RRR-00269.2025
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