Vacation Condo Rentals By Owner In Longboat Key, FL

$172.22

Beachplace 11-501 by FGC

Longboat Key, Florida, United States

2 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course with angled Gulf view and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. This is a very bright and cheerful condo The master suite with a king bed offers lush views and access to the balcony as well as a large tv. Primary bathroom offers a dressing area with 2 sinks and large closet and a walk-in shower with Grab bars. The kitchen offers a nice modern feel, laundry closet (washer/dryer) and full stainless appliances. All new windows and doors throughout the condo . Second bedroom has a king bed and bathroom has a tub/shower combo with grab bars. brbr Beachplace is a gated condominium with a variety of amenities including a long stretch encompassing 1,450 linear feet of the soft white sand beach. Chairs and Umbrellas are available for use. It also has a large heated pool , clubhouse, fitness center and 3 tennis courts plus pickelball. Town requirements are a 30 day rental and rentals are on a calendar month basis. Off-season may allow mid-month to mid-month. Washer/Dryer in unitbrbrRental includes Cable tv, High speed Wifi, telephone, parking, water and electric.brProperty books by the calendar monthbrbrManaged by FGC Vacation Rentals

2

Bed

2

Bath

4

Sleeps

Select Dates for Price

Condo

Beachfront 2 BR Corner Unit at Beachplace 1-401 by FVC

Longboat Key, Florida, United States

A luxurious beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowned Longboat Key and only minutes from St. Armand's Circle and downtown Sarasota.brbrBuilding 1, unit 401 at Beachplace is a two-bedroom, two-bathroom beachfront Longboat Key vacation rental most people only dream of experiencing! Perched on the 4th floor of a 6 floor building, you and your guests get to experience one of the most beautiful views on the Gulf Coast of Florida. brbrDecorated in neutrals and blues, you'll find the perfect space for family and friends to relax together around the large flat-screen TV in the open-concept living area. This is a corner unit, so the south wall of the living room has windows too, flooding the living room with glorious sunlight! The dining area offers seating for four with additional breakfast bar and balcony seating. The fully equipped kitchen features full-size stainless-steel appliances, granite counter tops, and includes all the cookware and dishware needed to create memorable meals together.brbrThe large master bedroom has a king bed, spacious closet, flat-screen TV, and private access to the beachfront balcony. The master bathroom features a large walk-in shower and double vanity. The guest bedroom has two twin beds, large closet, a flat-screen TV. Just steps from both the guest bedroom and living area is a full guest bathroom with a tub / shower combination.brbrThis condo is conveniently located a few miles from St. Armands Circle, with dining, shopping, and sightseeing just moments away. In addition to easy access to all that Longboat Key has to offer, this condo also has access to Beachplaces' on-site amenities, including a heated pool, three tennis courts and fitness room. Each building is equipped with an elevator and an assigned parking spot.brbrThis vacation rental is fully-stocked with linens, bath & beach towels. Pack light, as there is a washer and dryer in the unit for guest use.brbrThis unit offers high-speed Wi-Fi Internet access, perfect for streaming your favorite shows. We also can't think of a more inspiring work-space for those of you able to work remotely!brTown of Longboat Key RRR-00181.2023

Bed

Bath

Sleeps

$282.5

/ Nightly

Condo

Waterfront Longboat Key Retreat With Dream Views

Longboat Key, Florida, United States

Start your days waking up to waterfront views and end your days watching the sunset on the Gulf of Mexico from your private waterfront patio. This 2bd/2.5ba condo is ready to be your slice of paradise.brbrGulf front property with expansive waterfront views. Walking distance to 4 of Longboat's best restaurants. Includes Har-Tru tennis court, waterfront pool, and dock. Dedicated office space and workout room in the basement.brbrMin: 30 day

Bed

Bath

Sleeps

$419.56

/ Nightly

Condo

Stunning Gulf views - Gorgeous, Spacious, Just 5 steps to the sand!

Longboat Key, Florida, United States

Just you and the Gulf! Enjoy breathtaking sunsets from this, 1,488 sq. ft., beautiful 2 bedroom, 2 bath direct Gulf walk-out condo with views from most rooms. Newly renovated with lovely Coastal interior that can accommodate 6 comfortably with queen-sized pull-out sofa in the living room. Relax, unwind, fish, take a dip in the pool, walk the beach or simply chill with your favorite beverage. Close to everything…shopping and restaurants are just across the street or a short 5 minute drive to St. Armands., owntown Vibrant downtown Sarasota is just 15 minutes away and Anna Maria approximately 20 minutes or so. Enjoy cooking, watch the sea birds and listen to the waves while preparing a sumptuous meal. Privacy galore…the master bedroom features a king size bed, personal bath and walk-in closet. Your guests will enjoy the comfortable guest room with twins, desk and TV armoire. Your home away from home is well-stocked and offers wifi, flat screen TV’s and washer/dryer. No smoking or pets are permitted. brBeach chairs await, just bring your suit and sunglasses! brAccommodations and Amenities:brbrKing-sized bed in master bedroom.brTwin beds in second bedroom.brQueen sized sofa bed in living room.brTwo large flat screen TVs with HD programming and DVD in master bedroom.br29' LCD in spare room.brLocal phone service.brProperty manager available 24/7.brInternet wireless (WI-FI) in unit.brIn unit full size washer/dryer.brGulfside heated pool with lounge chairs and umbrella tablesbrPrivate white sand beachbrbrFor your convenience, just a short 3 minute stroll there's a great grocery store, pharmacy, fitness center, nail salon, liquor store and restaurants. Also nearby are churches, synagogue, banks, and post office. For those looking for other activities, there's a wonderful walking/bike path that runs the entire length of the Island. Many activities are locally available including golf, tennis, boating, fishing, and parasailing. Or --- you can relax, unwind and take in the amazing views...simply perfect. LOOKING for special dates, please let us know!!brbrKeywords: Beach view condo, Gulf views from most rooms, Fully stocked turnkey vacation retreat.

Bed

Bath

Sleeps

$646.69

/ Nightly

Private Vacation Home

Luxurious beachfront house on exclusive LONGBOAT KEY. Directly on the beach!

Longboat Key, Florida, United States

This exclusive beachfront house is located on the water's edge, directly on the Gulf of Mexico on sought after Longboat Key. A gem of mid-century modern architecture with a spacious floor plan and vaulted ceilings. When you step onto the rear deck, you walk out onto a pristine private beach and into the warm waters of the Gulf. This modern 4 bedroom, 2 1/2 bath, luxury property has all the amenities, including high end furniture, 4 flat screen TV’s, high speed fiberoptic internet and direct Gulf of Mexico views from nearly every room. brbrThe kitchen is fully equipped, all bedding, linens, towels and beach chairs are provided. This very spacious property is all on one level. A spectacular great room with floor to ceiling sliding glass doors opens up to a large, screened deck and adjacent open outdoor dining area, allowing you to kick back and relax and enjoy gulf front living at its finest. The house's western orientation gives you spectacular sunsets from nearly all rooms, patios and decks.brbrWhat’s better than your own private paradise You are close to all the amenities of Longboat Key, including local restaurants, the Avenue of The Flowers (Publix) shopping center, the Longboat Key tennis center and the Longboat Key Club with its two 18 hole golf courses. If that weren't enough, St. Armand’s Circle, known for its restaurants and boutiques is less than 10 minutes away and downtown Sarasota, with its culture and amenities, is only 15 minutes away! 30 minutes to IMG Academy!brbrMeticulously maintained and one of the only free-standing beach front houses available on Longboat Key.brbrKeywords: Luxury Beachfront House

4

Bed

2

Bath

8

Sleeps

$372.96

/ Nightly

Condo

Steps to the Beach! 3BR Condo w/ Pool, Hot Tub & Balcony

Longboat Key, Florida, United States

Your perfect Longboat Key escape awaits. This beautifully appointed three-bedroom, two-bathroom condo is just steps from the beach, offering the ideal blend of comfort, relaxation, and resort-style amenities. The condo features one king bed and two queen beds, comfortably accommodating families or groups, along with two full bathrooms designed with a clean, coastal feel. The bright, open living area flows seamlessly into a fully equipped kitchen, perfect for everything from casual breakfasts to evening dinners at home. Step out onto the private balcony to enjoy your morning coffee or evening breeze overlooking lush tropical surroundings. Guests also have access to exceptional community amenities, including a pool, hot tub, pickleball and tennis courts, and a fully equipped fitness center — everything you need for a true vacation experience. Ideally located, the condo is just a 5-minute drive to St. Armands Circle, known for its vibrant mix of restaurants, cafés, and boutique shopping, and only about 20 minutes from downtown Sarasota and Sarasota-Bradenton International Airport. After a day at the beach or exploring the area, return to the peaceful, laid-back atmosphere of Longboat Key to unwind and recharge. We’re always happy to share local recommendations and tips — feel free to reach out during your stay!

Bed

Bath

Sleeps

$410.01

/ Nightly

Apartment

Luxury Beachfront Retreat on Longboat Key

Longboat Key, Florida, United States

Summary:brbrEscape to paradise at this spacious 2-story beachfront retreat on Longboat Key! brbr- 2 bedrooms, 2 bathrooms, sleeps 6 brbr- Stunning Gulf views and private beach access brbr- Fully equipped kitchen and open-plan living room brbr- Heated community pool and shared hot tub brbr- 2-car garage for convenience brbr- Minutes from dining, shopping, and Sarasota’s charm brbrExperience comfort, space, and relaxation all in one place. Welcome to Your Luxury Beachfront Retreat on Longboat Key!brbrbrbrThe Space:brbrEscape to paradise at this spacious 2-story beachfront retreat on Longboat Key! With 2 bedrooms and 2 bathrooms, it sleeps up to 6 guests. Enjoy stunning Gulf views, private beach access, and a fully equipped kitchen. Relax in the common heated pool or unwind in the hot tub. Includes a 2-car garage for your convenience. Just minutes from dining, shopping, and Sarasota’s charm—this coastal getaway is perfect for families or groups. Experience comfort, space, and relaxation all in one place. Welcome to Your Luxury Beachfront Retreat on Longboat Key!brbrbrbrPerfect for large families or groups, this spacious 2-story home offers the ultimate coastal getaway with room for up to 6 guests. Located just steps from the Gulf of Mexico, this 2-bedroom, 2-bathroom property offers stunning views, a peaceful atmosphere, and top-tier amenities.brbrbrbrComfortable Accommodation:brbr- Bedroom 1: King Bed brbr- Bedroom 2: 2 Double Beds brbrbrbrInterior Feeling:brbr- Open-plan living room with ample seating brbr- Cozy atmosphere for relaxation brbr- Fully equipped kitchen with modern appliances brbrbrbrOutdoor Bliss:brbr- Private outdoor patio and green space brbr- Heated community pool for refreshing swims brbr- Shared hot tub for unwinding brbrbrbrDelightful Dining:brbr- Spacious dining area for family meals brbr- Easy meal prep in the fully equipped kitchen brbrbrbrProfessional Cleaning:brbr- Thoroughly cleaned and maintained for guest comfort brbrbrbrAttractions Nearby:brbr- St. Armands Circle (15 min): Upscale shopping, dining, and galleries. brbr- Mote Marine Laboratory & Aquarium (12 min): Fun and educational for all ages. brbr- Coquina Beach & Bayfront Park (10 min): Gorgeous public beaches and picnic spots. brbr- Downtown Sarasota (25 min): Theater, museums, nightlife, and cultural events. brbr- Longboat Key Golf Club (10 min): Beautiful courses and coastal views. brbr- Bike & Kayak Rentals: Easily explore the island’s scenic coastline. brbrbrbrYour Luxury Beachfront Retreat on Longboat Key!brbrbrbrGuest Access:brbrGuests will have exclusive access to the entire property, including the stylish living areas, fully equipped kitchen, and 2 comfortable bedrooms accommodating up to 6 guests. Outside, enjoy the community pool for relaxation and outdoor area. Amenities such as Wi-Fi, cable TV, and laundry facilities are provided for convenience.brbrbrbrThe Neighborhood:brbrThe neighborhood surrounding Gulf of Mexico Drive on Longboat Key is a tranquil and upscale coastal community, offering a serene environment for residents and visitors alike. This area is characterized by its low-density development, featuring a mix of luxury condominiums and private residences, many with direct Gulf of Mexico access.brbrbrbr Community AtmospherebrbrLongboat Key is known for its quiet, residential feel, making it ideal for those seeking a peaceful retreat. The community is pet-friendly, with many residents owning dogs, and features well-maintained streets and landscaping. While the area is car-dependent, it offers a safe environment with well-lit streets and a strong sense of community. brbrbrbr Beach AccessbrbrThe property is situated along the Gulf of Mexico, providing easy access to beautiful white-sand beaches and clear turquoise waters. Residents and guests can enjoy beach activities, sunbathing, and stunning sunsets just steps from their doorstep.brbrbrbr Dining and ShoppingbrbrWhile the immediate area is residential, nearby St. Armands Circle offers a variety of dining and shopping options. This vibrant area features upscale boutiques, art galleries, and a diverse selection of restaurants, providing a perfect spot for an afternoon out.brbrbrbr Outdoor ActivitiesbrbrFor nature enthusiasts, Longboat Key offers several parks and nature preserves. John M. Durante Park and Quick Point Nature Preserve are nearby, offering opportunities for kayaking, birdwatching, and enjoying the natural beauty of the area. brbrbrbrbrbr Golf and RecreationbrbrGolfers will appreciate the proximity to The Resort at Longboat Key Club, which offers an acclaimed 27-hole golf course. The club also provides tennis courts, a marina, and other recreational facilities, catering to a variety of interests. brbrbrbrbrbr ConveniencebrbrFor everyday necessities, Publix, CVS, and a post office are within easy reach, ensuring convenience for residents. The area also hosts community events, such as monthly concerts and holiday parades, fostering a strong sense of community among residents. brbrbrbrbrbrIn summary, the neighborhood around Gulf of Mexico Drive offers a blend of natural beauty, recreational opportunities, and a close-knit community, making it an ideal location for those seeking a relaxed and upscale coastal lifestyle.brbrbrbrGetting Around:brbrLongboat Key offers a laid-back, car-friendly lifestyle with scenic drives and easy access to nearby attractions. Here's what you should know about transportation in the area:brbrbrbr By Car:brbrMost residents and visitors rely on a car to get around Longboat Key. Gulf of Mexico Drive (SR 789) is the island’s main road, providing a beautiful, easy route north to Anna Maria Island or south to St. Armands Circle and downtown Sarasota. There's typically light traffic and ample parking at shops and beaches.brbrbrbr By Bike:brbrLongboat Key is bike-friendly, with well-maintained bike lanes and paths running along Gulf of Mexico Drive. It’s a scenic and safe option for getting around the island, whether you're headed to the beach or grabbing a bite to eat.brbrbrbr Public Transportation:brbrSarasota County Area Transit (SCAT) provides limited bus service to Longboat Key, with connections to Sarasota and surrounding areas. However, service can be infrequent, so it’s not ideal as a primary mode of transportation.brbrbrbr On Foot:brbrThe area is walkable for short distances, especially near the beach and local resorts, but a car or bike is recommended for reaching restaurants, shops, or parks further away.brbrbrbr Rideshare & Taxis:brbrUber and Lyft are available on the island, offering convenient options for airport transfers or nights out in Sarasota.brbrbrbrOther Things to Note:brbrCheck-out: We kindly ask that you check out on or before 11:00 AM on your departure date. This allows us enough time to clean and prepare the property for the next guests.brbrbrbrNo Pets allowed brbrbrbrNo Smoking: Smoking is strictly prohibited inside the condo and within any common areas of the complex. Please respect this policy to maintain a clean and smoke-free environment.brbrbrbrNo Parties: The house is intended for quiet and peaceful stays, and hosting parties or large gatherings is not allowed. Please be considerate of the neighbors and keep noise levels to a minimum, especially during nighttime hours.brbrbrbrThese policies are in place to ensure a comfortable and enjoyable experience for all guests and to maintain the integrity of the property. brbrbrbrbrbrIf you have any questions or need further clarification about these policies, please feel free to contact us. We want to ensure that your stay is pleasant and in accordance with these guidelines.brbrbrbrInteraction with Guests:brbrCheck-In: Prior to your arrival, we will provide you with detailed instructions on how to access the condo. If you have any questions or need assistance during the check-in process, we are just a phone call or message away.brbrbrbrCommunication: We are available to address any questions, concerns, or issues you may have throughout your stay. We strive to respond promptly and provide you with the support you need to make your stay comfortable.brbrbrbrRecommendations and Assistance: If you need recommendations for local attractions, dining options, or any other information about the area, please don't hesitate to ask. We are familiar with the surroundings and can provide guidance to enhance your experience.brbrbrbrEmergencies: In case of any emergencies or urgent matters, please refer to the provided emergency contact information. We will provide you with the necessary assistance to address the situation promptly.brbrbrbrWe aim to strike a balance between respecting your privacy and ensuring you have a pleasant and hassle-free stay. Our goal is to make your experience enjoyable and memorable. If you have any specific preferences or requirements regarding our interaction, please let us know, and we will do our best to accommodate them.

Bed

Bath

Sleeps

$306.76

/ Nightly

Private Vacation Home

Peaceful Condo – Cedars East #803 by RVA

Longboat Key, Florida, United States

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrbrDiscover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gulf Coast. Imagine waking up in a spacious, beautifully appointed townhome—perfect for families seeking fun-filled adventures or couples looking for a romantic retreat.brbrbrHere, every day is an invitation to indulge. Step outside and be greeted by world-class tennis courts, ideal for both casual play and competitive matches. Dive into the sparkling junior Olympic-sized swimming pool or enjoy a rejuvenating workout at the state-of-the-art fitness center. Cast a line from the fishing pier, explore the island on complimentary bicycles, or simply unwind as you watch tropical sunsets paint the sky in unforgettable hues.brbrbrAccommodations: Cedars Tennis Resort is a village-like town home community that features spacious living and dining areas and full-size kitchens. Enjoy all the amenities of home in these fully furnished condominiums including full-sized kitchen with breakfast bar, separate dining area and private lanai (available in select units).brbrbrClub and Recreation Facilities: Tennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brbrbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrbrDining and Social Spaces - Hugo II Restaurant - A European Fusion restaurant offering German, Czech, and Italian dishes plus specialty Prosecco cocktails; private dining memberships required (no extra cost for Club members). Open Seasonally.brbrbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrbrFishing Pier and Mangrove Boardwalks - Charming wooden boardwalks wind through mangroves, leading to a serene fishing pier—perfect for picnics or watching boats and marine life. brbrbrBeach Access Information - The beautiful Gulf of Mexico shoreline stretches north and south along Longboat Key, and guests are welcome to enjoy it by using any designated Public Beach Access point. These access points are clearly marked with signs indicating Public use. Please note: Private beach access points along Gulf of Mexico Drive are reserved for property owners and their guests. Unless an access point is clearly labeled as Public, it is not available for use. We encourage you to explore and enjoy the public areas of the beach and thank you for respecting local property boundaries.brbrbrResidential and Guest Accommodations - Townhomes - Tri-level, spacious units featuring full-size kitchens, screened lanais or private balconies, and comfortable living/dining areas. The community is divided into three sections—The Gardens (500s), Club Level (600s), and Preserves (800s)—all connected via picturesque boardwalks.brbrbrUnit #803 Accommodations: 2-bedroom, 2.5 bathroom townhome with garden views in the private Preserves location of Cedars community.brbrbrbrUnit Amenities: Wireless Internet, Full-size Kitchen, Private Lanai, Fitness Facility, Community Pool, Beach Access (A Short Distance Away)brbrLocation: 803 Evergreen WaybrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, 2 Twins, Sleeper SofabrbrbrbrMinimum Night Requirements: Minimum Stays Apply

2

Bed

2

Bath

6

Sleeps

Select Dates for Price

Condo

Beachfront Condo On Longboat Key - First Floor

Longboat Key, Florida, United States

Direct waterfront on Longboat Key. Unobstructed views of the Gulf of Mexico. This first-floor beachfront condo has everything you need for your stay. The Gulf of Mexico is mere steps from your own lanai. Beach chairs and umbrellas are on the beach waiting for you. Open the sliding door and windows and let the Gulf soothe you. 3 miles to the famous St. Armands Circle and vibrant downtown Sarasota. Community has 2 heated pools, hot tub, walking paths and kids play area. brbr*Minimum stay 2 months*

Bed

Bath

Sleeps

$234.41

/ Nightly

Private Vacation Home

Canal front home on Longboat Key -Just Steps to the Beach

Longboat Key, Florida, United States

Newly renovated and spacious canal-front home in beautiful Longboat Key with deeded beach access just steps down the street. This charming coastal retreat comfortably accommodates up to 5 guests and offers the perfect blend of relaxation, convenience, and waterfront living.brbrThe primary bedroom features a plush king-sized bed, while the second bedroom includes two twin beds—ideal for families or friends traveling together. The cozy sunroom offers additional sleeping space with a sofa bed for one guest.brbrThe stunning open-concept kitchen has been fully updated with brand-new stainless steel appliances and is fully equipped for cooking, entertaining, and gathering with your group. Large windows throughout the home fill the space with natural light and showcase beautiful canal views.brbrOutside, enjoy true Florida waterfront living with private canal frontage and pilings available for docking your boat. After a day at the beach or out on the water, rinse off in the convenient outdoor shower.brbrBoth bathrooms have been tastefully updated, including a beautifully renovated main bathroom and a stylish second bath featuring state-of-the-art lighting with integrated Bluetooth audio.brbrIdeally located in the heart of Longboat Key, the home is within walking distance of fine dining, convenience stores, and bike rentals, and just a short drive to St. Armands Circle, Mote Marine Laboratory & Aquarium, and all the attractions of Sarasota.brbrPerfect for beach days, boating adventures, and relaxing coastal getaways.brbrFor more photos, follow our instagram page:br @beachbreezebungalow

Bed

Bath

Sleeps

$312.62

/ Nightly

Condo

Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10

Longboat Key, Florida, United States

Welcome to Unit 10 at Cabana Beach Club, a beautifully renovated, exceptionally private bayfront condo located on iconic Longboat Key. This peaceful retreat sits directly on the bay, where you can watch manatees right from your doorstep, while the Gulf of Mexico’s stunning beaches are just across the street.brbrCabana Beach Club is a boutique community of only 11 units, and this condo is part of the exclusive canal-side section with just three units, offering a truly quiet and private waterfront setting.brbrThis one-bedroom, one-bathroom condo comfortably accommodates up to four guests, featuring a pullout sofa in the living room, a dining area, and a fully stocked kitchen. Step out onto the private patio with a cozy seating area, perfect for morning coffee or an evening glass of wine while enjoying tranquil bay views.brbrModern comforts include smart TVs in every room, free Wi-Fi, and a washer and dryer inside the unit. Convenient parking is located right by the condo, and boat trailers can be accommodated—just confirm with the owner in advance.brbrGuests also enjoy access to a heated pool located on the beach side of the Club, as well as a nearby convenience store within walking distance.brbrFresh, stylish, and thoughtfully equipped with everything you may need (and maybe a few things you don’t :)), Unit 10 is the perfect place to relax, recharge, and experience the best of bayfront and beachside living.brbrTraveling with family or friends We own all three canal-side units—ask about Units 11 and 12 when planning a group or family stay.

Bed

Bath

Sleeps

$252.63

/ Nightly

Villa

Updated Villa Condo -Steps to Beautiful White-Sand Beach

Longboat Key, Florida, United States

Our lovely two-bedroom, single-story, villa is ideally situated within the 20+ acre Whitney Beach Resort located on exclusive Longboat Key. The expansive resort straddles both our private, white powder, Gulf of Mexico beach and the beautiful waters of Sarasota Bay. The beach and the dock area are each a short 200' walk from the front door of the villa. Surrounded by pristine, tropical gardens, our pool is 20' from our rear sliding doors. Both our private dock/fishing areas and our private beach offer chaise lounge chairs for the use of the members. Our unspoiled, deeded beach, is a shell hunter's dream. brbrOur newly updated, clean, and freshly painted villa offers a king sized bed in the Master bedroom with a custom, queen size, pull-down 'Murphy' bed in the spare bedroom. The spare bedroom also serves as an office. In the living area, a queen-size pull out couch can accommodate additional sleepers. The updated appliances, electronics and tastefully appointed furnishings truly make this a 'home away from home.' brbrThe property includes tennis courts, shuffleboard courts, a community tiki hut by the sea for entertaining, and a community grill. Our unit has two bicycles for guest use.

Bed

Bath

Sleeps

$324.28

/ Nightly

Cottage

Historic Longbeach Village Cottage - Private Home

Longboat Key, Florida, United States

brbr 'Sunny Side Up' is a restored beach cottage built in the 1950's located on the north end of Longboat Key in historic Longbeach Village. The feel of Old Florida with all the modern conveniences. brbrNewly Remodeled and Fully furnished kitchen with breakfast bar includes stainless appliances including dishwasher, cookware and dishware - opens to den featuring french doors.brbr Brand new flooring throughout. brbrNew vanities in bathrooms.brbrWall Mounted Flat Screen HDTVbrbrSecured WIFI InternetbrbrSecluded in a private lush tropical garden with outdoor deck patio, you can also 'Get Away from It All'.brbr'Sunny Side Up' is a short stroll from waterside dining at Shore Restaurant and Mar Vista Restaurant and Pub where you can watch the dolphins feed. Whitney's is also just a short stroll. Just minutes away is St. Armands Circle for loads of shopping and dining fun. Have I mentioned gorgeous Whitney Beach isbrjust a short walk away It is not uncommon to view dolphin and manatee if you watch carefully.brbrBuilt when they knew how to build featuring Tongue and Groove paneling throughout, and large windows to watch for peacocks.brbr3 Bedrooms with 1 King and 2 Twin over Full Bunk Bedsbrbr2 full bathrooms indoors - one updated with large step in shower, other has tub/showerbrbrPrivate Outdoor ShowerbrbrLarge outdoor deck area with table for six and lounge seating area by gas grill.brbrAttached garage/screened in outdoor dining area.brbrFull Sized Washer / Dryer.brbrWe also provide Bikes, Beach Towels, Chairs and Umbrellas.brbrOutdoor activities abound with boating, fishing, kayaking, parasailing, jet ski, and bicycle rentals all nearby. Bike trails and sidewalks can take you the length of the island.brbrJust North over the bridge is Anna Maria Island with all itsbrrestaurants and beach shops.brHeading South you are a short bike ride or 2 mile walk from Joan M. Durante Park, Recipient of '1998 Outstanding Ecosystem Restoration Award' withbrwinding plank trails overlooking Sarasota Bay and a great kids playground. Mote Marine Laboratory invites you to observe Florida sea life including dolphins, manatees, and seahorses.brbrSarasota is just over the bridge from St. Armands Circle with theaters, opera, symphony, museums and art galleries, and, if you time it right, the Pittsburg Pirates train in nearby Bradenton.brbrHave I mentioned gorgeous Whitney Beach is just a short walk away brbrHope you can come and Enjoy!

Bed

Bath

Sleeps

$371.0

/ Nightly

Condo

Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

Longboat Key, Florida, United States

Discover Your Dream Escape at Cabana Beach Club Unit 9 on Longboat Key!brbrWelcome to your newly remodeled Gulf-side retreat, perfectly situated in the heart of charming Longboat Key. This lovely unit accommodates up to 5 guests and features 1 bedroom and 1 bathroom, making it an ideal choice for both romantic getaways and family vacations.brbrStep inside to find a fully equipped kitchen complete with modern appliances, a new fridge, and all the cookware and utensils you’ll need to enjoy meals together. The cozy master bedroom boasts a king-size bed, while the living room offers a sleeper sectional and a pullout chair, comfortably sleeping five in total. With linens and towels provided, you can focus on relaxing and enjoying your stay.brbrThe unit is beautifully decorated in a Florida beach theme, creating the perfect ambiance for your coastal escape. Enjoy entertainment with flat-screen smart TVs in both the living room and bedroom, along with high-speed internet and cable access. We also provide a starter supply of essential items, including paper towels, coffee filters, and laundry detergent for your convenience. Washer and dryer located inside.brbrStep outside to enjoy direct beach access, where you can soak up the sun on the soft, white sands or take a dip in the heated pool just steps from your door. For those looking to explore the waters, our boat and fishing dock is available, with rental slips offered at an additional fee.brbrLongboat Key is the crown jewel of the Gulf of Mexico, offering a tranquil setting to unwind and recharge. Go for a leisurely walk along the shoreline, catch breathtaking sunsets, practice yoga at sunrise, or enjoy a refreshing swim in the warm turquoise waters. Spend your days fishing or barbecuing on the beach while watching dolphins and manatees play nearby.brbrOur prime location places you just minutes away from a variety of restaurants, shops, and water sport rentals. Experience the vibrant nightlife and cultural events in nearby Sarasota, or visit the famous St. Armand’s Circle for shopping and dining.brbrMake Cabana Beach Club Unit 9 your home away from home on Longboat Key. Book your unforgettable beach getaway today!br

1

Bed

1

Bath

5

Sleeps

$115.25

/ Nightly

Private Vacation Home

Bermuda-esque Island Cottage! Steps to Sand! Beach to Bay

Longboat Key, Florida, United States

Escape to this cozy, light-filled cottage, completely rebuilt in 2025 with a brand-new kitchen featuring stainless steel appliances. Enjoy a comfy full bed in a loft-like setting, commercial-speed WiFi, 2 TVs, and in-unit laundry. The perfect serene hideaway for lovebirds seeking a peaceful retreat! Light & bright with windows scattered throughout make this an ideal work setting. Fully gated & landscaped yard with gas grill & firepit. Parking for one vehicle off a small shell road with a separate space large enough for a Suburban. brbrYou are located on Broadway at Poinsetta in the Village on Longboat Key, also known as Longbeach. All of our streets are nature inspired with no parking allowed! It is quiet here & you'll enjoy a breeze all day everyday with access to the beach and bay! Here, you are a 450' walk to the Sarasota Bay, Mar Vista. Or walk across Gulf of America to Whitney Beach - just 450' west!

Bed

Bath

Sleeps

$689.4

/ Nightly

Private Vacation Home

Waterfront Coastal 3 BR/3 BTH w/ Pool, 50ft. Boat Dock, Walk to Beach

Longboat Key, Florida, United States

Stunning, newly renovated 3BR/3BTH home on preferred southern end of Longboat Key. Luxury interior design features cozy, oversized Restoration Hardware furniture, high-end linens, fully appointed gourmet kitchen, large master bath with Jacuzzi overlooking canal, and more. Whether it's a fun day a day at the beach or dinner and game night with friends, this 2500 sq. ft.-home has everything you need.brbr* Open floor plan with two distinct living areasbr* Large dining room seats 8br* Poolside table seats additional 6br* Premium cable and 4 new Hi-Def flat screen TV's br* Brand new private dock with easy access for all water sportsbr* Kayaks and paddle-boards included

3

Bed

3

Bath

8

Sleeps

$142.07

/ Nightly

Private Vacation Home

Classic Cottage w/Boat Parking! Steps to Sand!

Longboat Key, Florida, United States

Discover this quaint one-bedroom guest house tucked away in a peaceful corner. Perfect blend of classic charm and modern comforts such as high vaulted ceilings, a modern kitchen; a true getaway! Enjoy the luxury of high speed internet, a reverse osmosis H20 system & brand new washer/dryer in-closet for added convenience. Breathe freely with UV air filtration system. Boat parking & public boat launch nearby! Perfect for 2 lovebirds seeking romance by the beach!

Bed

Bath

Sleeps

$417.73

/ Nightly

Condo

Sun Salt Sand: Open Sun - Wed!

Longboat Key, Florida, United States

This sublime oceanfront condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!brbrAlso, if you want to vacation with friends or family, we own a downstairs unit, #103, and another top floor unit, #221, as well...!brbrUpon arrival to The Beach on Longboat Key Resort, you will be wowed by this tropical property! Conveniently located mid-island on Longboat Key, on Gulf of Mexico Drive, this small, intimate resort, only 15 units, has so much to offer: direct, private beach access, heated pool, BBQ grill, pool and beach loungers, and onsite laundry.brbrWhen you arrive, make your way to our condo, Unit 224, on the second floor, for optimal sunset viewing, dolphin observing, and manatee spotting...! The condo has a coded lock for smooth entry and exit and freedom from losing a key on the beach...!brbrUpon entering, you will walk through a small entryway to view the main living space. Our condo features a queen-size bed, along with a queen-size sleeper sofa for the extra members of your party - the little ones! There are two Smart televisions, with cable, for entertainment when you're not beaching it, along with a variety of reading material, board games, and children's toys. WiFi, of course, is available throughout! Also, there is a closet and chest of drawers for storing belongings for a quick weekend getaway or a month-long stay...! For family use, we have a Pack 'N Play - convenient!brbrThe kitchen, with granite countertops and stainless steel appliances (dishwasher!), is fully stocked (coffee maker - drip and Keurig, blender, Tupperware, knife set, wine glasses, etc.), including everything you might need to cook meals in on the days you prefer not to dine out...!brbrThe bathroom features a combined tub and shower, which always comes in handy when traveling with children!brbrBeyond the main living space is a large, private lanai, with high top table, two chairs, and lounger ideal for eating a meal or sipping a cocktail! There is also a deck box with beach toys!brbrThe condo has both central heat and air, along with an additional floor fan. There is a smoke detector and fire extinguisher, as well.brbrOn property, there is a heated pool with deck and loungers! Grab a sun umbrella from our closet and stroll down to the private beach with more lounge chairs. No need to bring your own!brbrA propane grill is on the lawn with grilling utensils in our unit!brbrOn the ground floor of The Beach complex, there is a free washer and dryer if needed during your trip. There is also a main dumpster for easy trash disposal.brbrThe best part of our condo is the direct, unobstructed ocean view and private beach access - just sublime!brbrNotes:brbr1. Upon arrival, the condo will be prepared with fresh bed linens, bathroom towels, and beach towels. brbrThere will also be starter supplies of the following:brbrBathroom:br- toilet paperbr- shampoo & conditioner br- body washbr- hand soapbr-hair dryerbrbrKitchen:br- dish soap & spongebr- paper towelsbr- dishwasher detergent br- trash bagsbr- aluminum foilbr- plastic storage bagsbr- cleaning spraybr- spicesbr- olive oilbr- coffee filters - drip & Keurig!br- ice cube traysbrbrCloset:br- iron & ironing boardbr- laundry detergent br- rain umbrellabr- sun umbrellabr- folding beach chairsbr- beach wagonbr- vacuumbr- broom & dustpan brbrDaily housekeeping service is not available unless you would like to request a mid-stay clean for an extra fee, which I can arrange for you...! Sometimes that can come in really handy!brbr2. For our condo, there is one parking spot available - park wherever you like within the lot! Due to the size of the parking lot, unfortunately, no guest cars or trailers can be accommodated because it will take a spot away from another condo.brbr3. Please note our condo is a one-bedroom best suited for one-two adults or one-two adults plus one-two children in the sleeper sofa, and/or one in the Pack 'N Play, if needed. Unfortunately, we cannot accept reservations for over two adults due to sleeping arrangement comfort. If it is a unique situation, feel free to message me to discuss further. Thank you for your understanding!brbr4. The condo is located on the second floor... for a stunning view! At the complex, there are stairs, but no elevator.

Bed

Bath

Sleeps

$404.91

/ Nightly

Condo

Longboat Key Beachfront - Beautifully Updated with Prime Location

Longboat Key, Florida, United States

Come enjoy this beautiful beachfront condo! brbrCompletely renovated and updated,, this condo is located at the desirable north end of Longboat Key on one of the most beautiful beaches on the West Coast: white sand, shells, no crowds. The complex has only 64 units in four, 2-storey buildings; all units have their own private outside entrance. This unit is on the second floor where the ocean views are spectacular, including gorgeous sunsets. The condo is done in soothing beach colors (light yellow, blue, white and coral). The living area and master have mirrored walls, enhancing the views, and both open onto a large screened lanai. The living area has a queen sleeper sofa, love seat, chair and ottoman. There is a large TV with DVD. The dining has a table that will seat 10 and a buffet/server. There is colorful art throughout. The kitchen opens onto the dining area to give a light, open feeling. There is a small den off the kitchen with a full-size sleeper sofa and a closet with washer and dryer. Completely furbished, the kitchen has service for 12, many serving dishes and extra appliances including a Keurig coffee maker and an electric wok. The master suite has a king bed, dresser and a flat screen TV. Open the sliding doors to listen to the ocean, or close the room-darkening blinds if you want to sleep late. There are both a dressing area and a bathroom with shower off the master suite as well as a walk-in closet. New cabinets and granite counters can be found in both bathrooms. The second bedroom has twin beds, a single sleeper chair, a flat screen TV and its own complete bath. The beachfront pool can be accessed from the beach or the parking area and there are 2 tennis courts across the street for the exclusive use by Cedars West residents and guests. A barbeque grill is available on site.brbr(Please note that the Cedars West Condominium Association does not permit rentals for fewer than TWO WEEKS).br brLongboat Key is close to both Bradenton and Sarasota, one of the cultural centers of the West Coast. Activities abound for everyone. Nearby are fine and casual dining, golf, parasailing, diving, kayaking, theater, movies, opera, night life. Kids can have fun at Jungle Gardens, Mote Marine or playing miniature golf. Go deep sea fishing and cook your catch in your own kitchen. Plan a morning shopping in the upscale shops on St Armand's Circle and have lunch at the Columbia or another of St Armand's fine restaurants. Rent a bike or take the free trolley up to Bradenton Beach to have a beachfront meal. This is the place for you if you are looking for a relaxing and fun stay at the beach. brbrKeywords: Beachfront, Beach, Longboat Key, Cedars West, Gulf Coast, quiet, calm, waterfront, tennis, Pool

Bed

Bath

Sleeps

$265.17

/ Nightly

Private Vacation Home

3brm elevated canal front pool home on North Longboat Key

Longboat Key, Florida, United States

Welcome to Coconut Place: Your Canalfront Paradise!brbrPrepare to be captivated by the stunning Coconut Place, a beautifully designed 3-bedroom, 3-bath canalfront home, expertly managed by FL Vacation Connection. From the moment you arrive, this tropical oasis will leave a lasting impression.brbrAs you step onto the property, you’re greeted by lush, tropical landscaping and expansive decks that offer breathtaking views of the water. The plush green lawn gently slopes down to your very own private dock—perfect for casting a line and reeling in tonight’s fresh catch. The spacious wood deck provides an idyllic spot to sip your morning coffee, lounge with a good book, or simply watch the boats glide by. It’s your front-row seat to paradise, and it might just become your favorite place to unwind.brbrBut wait until you see the pool! This 12 x 20 sparkling inground pool, surrounded by elegant brick pavers, could easily become your go-to spot for relaxation. With both open and covered seating areas, you’ll have plenty of options to soak up the sun or enjoy the cool shade beneath a majestic tree that completes this perfect outdoor retreat.brbrInside, Coconut Place continues to impress with its clean, sophisticated decor. The spacious great room invites you to sink into a brand-new sectional sofa, where the whole family can gather after a fun-filled day. Whether you’re catching up on your favorite TV shows or enjoying a movie night on the flat-screen TV, comfort is key. The adjacent dining area, with seating for four and additional bar stools at the breakfast bar, is ideal for family meals or casual snacks.brbrThe kitchen is a gourmet’s dream, fully equipped to handle everything from quick bites to elaborate feasts. You’ll find everything you need to create delicious meals that you can enjoy in the comfort of your home away from home.brbrEach of the three bedrooms offers its own private ensuite bath, ensuring maximum privacy and convenience. The master suite is a sanctuary, featuring a luxurious soaking tub and a separate shower for a true spa-like experience. Whether you choose the King master, Queen master, or the Twin bedroom, you’re guaranteed a restful night’s sleep.brbrAt Coconut Place, every detail is designed with your comfort and enjoyment in mind. Come and discover the ultimate vacation experience in this canal front haven you’ll have everything you need and more for a truly unforgettable stay.brbrTown of Longboat Key RRR.00203.2023

3

Bed

2

Bath

6

Sleeps

Vacation Condo Rentals By Owner In Longboat Key, FL

$172.22

$282.5

$419.56

$646.69

$372.96

$410.01

$306.76

$234.41

$312.62

$252.63

$324.28

$371.0

$115.25

$689.4

$142.07

$417.73

$404.91

$265.17

Rent a place that suits your needs

Most popular vacation rentals in Longboat Key

$747.69

$2112.85

$1196.70

$1148.84

$1024.99

$884.08

$861.14

$767.89

$755.36

$670.46

Most Popular Cities in Florida