1669 Holiday rentals and Airbnb in Longboat Key, FL
9.2 104 reviews
Longboat Key, FL
10/10 – 17/10
241 €/nighttotal: 1687 € (7 )
Gulf Front Escape Silver Sands #252 By Rva
1 4
apartment , Longboat Key
Silver Sands #252 Resort By Rva is situated on Longboat Key beach, just 3km from Coquina Beach and Bradenton Beach, with Longboat Key Beaches and Cannons Marina within a 1km walk. This property has received excellent guest ratings and is a popular choice for travellers seeking a relaxing beach getaway. The apartment can accommodate up to 4 guests and offers a comfortable living space with a fully equipped kitchen and a terrace. Guests can enjoy the on-site amenities, including a swimming pool, tennis court, and barbecue facilities, as well as access to the beach and local attractions.
Longboat Key, FL
01/11 – 01/04
347 €/nighttotal: 52397 € (151 )
Luxury Coastal Escape In Longboat Key, Florida-beachfront Condo For Rent!
2 2
apartment , Longboat Key
This sixth-floor condominium in Longboat Key provides direct ocean and bay vistas, located a mere few kilometres from the shops and restaurants of St. Armands Circle. This 147 square metre apartment accommodates up to four guests, featuring two bedrooms and two bathrooms, with resort-style amenities including a heated swimming pool, spa, and direct access to 400 feet of private coastline.
Longboat Key, FL
27/06 – 04/07
284 €/nighttotal: 1988 € (7 )
139 M² House ∙ 2 Bedrooms ∙ 5 Guests
2 2
house , Longboat Key
This fisherman's cottage is located in Longboat Key, just 450 metres from the Sarasota Bay boat ramp and a short walk to Whitney Beach. This property offers 139 square metres of living space with two bedrooms, two bathrooms, and accommodation for up to five guests, featuring a well-equipped kitchen, two living rooms, a private patio, and access to a swimming pool, fitness centre, and tennis court.
9.3 27 reviews
Longboat Key, FL
01/07 – 05/07
454 €/nighttotal: 1816 € (4 )
Blue Chill! Heated Pool Home W/grill! 15 Min Drive To The Beach!
3 8
apartment , Bradenton
This three-bedroom home is situated in Northwest Bradenton, just off 75th St W, offering easy access to Lakewood Ranch, Sarasota, and Tampa, as well as a short drive to the beaches of Anna Maria Island, Bradenton Beach, and Holmes Beach. The property has received excellent ratings for user experience, location, and cleanliness. This 172 square metre property offers comfortable accommodation for up to eight guests. Enjoy a relaxing vacation with a private saltwater pool, a screened-in pool area, a large covered area, and a private full bathroom accessible from the pool deck, a fully equipped kitchen, a high chair and pac-n-play for families with young children, and a convenient self check-in with a smart lock.
9.8 136 reviews
Longboat Key, FL
01/07 – 05/07
14725 €/nighttotal: 58900 € (4 )
The St. Regis Longboat Key Resort
1 8
resort , Longboat Key
The St. Regis Longboat Key Resort is located on Longboat Key, within 5 kilometres of Longboat Key beaches, Harborside Golf Course, and Islandside Golf Course, offering a peaceful retreat with easy access to local attractions. The resort features a range of luxury rooms and suites, all with modern amenities and comfortable furnishings. The resort boasts a private white sand beach, a full-service spa, three on-site restaurants, a fitness centre, and a swimming pool, ensuring a relaxing and enjoyable stay for all guests.
9.6 8 reviews
Longboat Key, FL
01/07 – 08/07
330 €/nighttotal: 2310 € (7 )
Beachcomber Unit 203
1 2
apartment , Longboat Key
This beachfront Longboat Key apartment is situated near Publix and CVS, offering easy access to Sarasota Bay. The two-bedroom, one-bathroom condo sleeps four, features a fully equipped kitchen, two smart TVs, a terrace, and access to a heated swimming pool; king-size bed and full-size sleeper sofa are provided.
8.6 128 reviews
Longboat Key, FL
10/10 – 17/10
300 €/nighttotal: 2100 € (7 )
2nd-floor Gulffront Outrigger #6 Condo By Rva
1 4
apartment , Longboat Key
Outrigger Resort #5 Condo By Rva is located on Longboat Key, just 0.5km from the beach and 2.1km from Cannons Marina, offering a peaceful escape from the hustle and bustle. It's rated very good by previous guests. This self-catering apartment is 98 square metres and has a balcony with a view. Guests can enjoy a range of amenities, including a swimming pool, a garden, and barbecue facilities.
10 1 review
Longboat Key, FL
01/11 – 01/04
185 €/nighttotal: 27935 € (151 )
2 Bedroom Longboat Key Beachside Paradise. Steps From The Beach!
2 2
apartment , Longboat Key
This Longboat Key apartment, near a tranquil beach and a short shuttle ride from St. Armands Circle, offers easy access to Publix supermarket and is approximately 32km from Sarasota Bradenton International Airport (SRQ). The two-bedroom, two-bathroom flat sleeps six guests and boasts stunning Gulf and Bay views, a private balcony, a heated swimming pool, tennis courts, and direct beach access across the street.
8.6 4 reviews
Longboat Key, FL
08/10 – 12/10
397 €/nighttotal: 1588 € (4 )
Beach Castle Resort, 2nd Floor, Updated, Walk To Beach/bay, Pool
3 6
apartment , Longboat Key
Beach Castle Resort, a 94 square metre (1012 square foot) three-bedroom apartment on Longboat Key, is situated less than 1.6km from Longboat Key Beaches and Cannons Marina, and within 9.6km of Jewfish Key and Coquina Beach. This self-catering condo, offering a terrace, pool, spa, and tennis court, sleeps six guests and includes a fully equipped kitchen, two bathrooms, and a sofa bed.
9.5 312 reviews
Longboat Key, FL
20/07 – 22/07
263 €/nighttotal: 526 € (2 )
Beach Front One Bedroom Condo Paradise. Ground Floor.
1 1
apartment , Longboat Key
This studio apartment is located on Longboat Key, just a 2-minute walk from the beach and 19 kilometres from the John and Mable Ringling Museum of Art. It has received excellent ratings for its location, cleanliness and overall experience. The apartment is on the ground floor, offering easy access and a private balcony. Guests have access to a range of amenities including a well-equipped kitchen, a swimming pool, a jacuzzi, a tennis court and free parking.
Longboat Key, FL
08/10 – 12/10
306 €/nighttotal: 1224 € (4 )
Silver Sands #251s
1 6
house , Longboat Key
This Silver Sands #251S property is a beachfront apartment in Longboat Key, offering direct access to the beach and situated 24 kilometres from the John and Mable Ringling Museum of Art. This apartment accommodates up to 11 guests and features a well-equipped kitchen, two bathrooms, a balcony with sea views, air conditioning, a swimming pool, a garden, a fitness centre, a tennis court, and complimentary private parking and WiFi.
Longboat Key, FL
01/11 – 01/04
261 €/nighttotal: 39411 € (151 )
Beachfront Vacation Rental With Full Gulf Views!
2 2
apartment , Longboat Key
This waterfront condominium in Longboat Key offers direct access to Longboat Key Beaches, a mere 5-minute walk away, and is a 13-minute drive from Lido Beach, with Cannons Marina and the Longboat Key Public Tennis Centre also within easy reach. This two-bedroom, two-bathroom apartment accommodates up to four guests and features complimentary Wi-Fi, a television, a DVD player, an on-site sauna, a swimming pool, and a terrace or balcony for enjoying the surroundings.
Best family friendly Longboat Key, FL holiday rentals
Among the 1669 accommodations in Longboat Key, FL, here are the 4 best family friendly rentals
Longboat Key, FL
08/10 – 12/10
362 €/nighttotal: 1448 € (4 )
Gulf-view Beachfront Condo Unit 203 Longboat Key
1 6
apartment , Longboat Key
This beachfront condominium on Longboat Key offers direct access to a private beach, situated a mere 1-minute walk from Longboat Key Beach and 20.9 kilometres from the John and Mable Ringling Museum of Art. This family-friendly apartment spans 65 square metres, accommodating up to 11 guests with one bedroom and one bathroom, and features a fully equipped kitchen, air conditioning, a swimming pool, a private balcony, and complimentary WiFi and parking.
10 2 reviews
Longboat Key, FL
16/07 – 21/07
178 €/nighttotal: 890 € (5 )
Cd Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img
2 2
apartment , Bradenton
This Bradenton apartment, near IMG Academy (a 5-minute drive away), offers easy access to Anna Maria Island and Longboat Key beaches (approximately 24km). The 106 square metre, two-bedroom, two-bathroom property sleeps four, boasting a terrace, garden, and access to resort amenities including heated pools, tennis/pickleball courts, and a clubhouse with BBQ grills.
9.4 166 reviews
Longboat Key, FL
14/07 – 16/07
374 €/nighttotal: 748 € (2 )
Water Slide & Pool ** Sugar Shack**
3 4
apartment , Bradenton
This Bradenton property is conveniently located within 5 kilometres of Blake Medical Center, LECOM Park, and Riverwalk, offering easy access to the area's attractions. The property has consistently received excellent guest ratings for its location, cleanliness, and overall experience. The house features three bedrooms, providing comfortable accommodation for families or groups of friends. Guests can enjoy a range of amenities, including a private garden, a swimming pool, a jacuzzi, and a fully equipped kitchen.
9.4 62 reviews
Longboat Key, FL
08/10 – 12/10
531 €/nighttotal: 2124 € (4 )
Beachfront Villa On Serene Gulf Of Mexico
2 6
apartment , Longboat Key
This beachfront apartment is located on Longboat Key, just under two hours from Orlando's theme parks, 45 minutes from Tampa's Busch Gardens, and 10 minutes from Sarasota's St. Armand's Circle, offering a peaceful escape from the hustle and bustle. It has received excellent user ratings for its comfortable and convenient amenities. The apartment features two bedrooms and two bathrooms, spanning 92 square metres and accommodating up to six guests. Enjoy the private beach, heated pool, screened balcony with Gulf views, and the convenience of a full-sized washer and dryer.
Best Longboat Key, FL holiday rentals with a pool
Among the 1669 accommodations in Longboat Key, FL, here are the 4 best rentals with a pool
9.0 48 reviews
Longboat Key, FL
08/10 – 12/10
411 €/nighttotal: 1644 € (4 )
Beachfront Bliss: Beach Castle #1 By Rva
2 6
apartment , Longboat Key
This ground-floor flat is situated on the Gulf side of Beach Castle Resort on Longboat Key, offering beach views from its private patio and is a short walk from the resort's community pool and hot tub, as well as Longboat Key's popular restaurants and shops. It has received excellent ratings for its location, cleanliness, and overall user experience. The flat has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a private patio, access to a heated pool, a hot tub, and a shared boat dock, as well as temporary membership privileges at Cedars Tennis Resort, granting access to tennis courts, community bicycles, a fishing pier, and a Jr. Olympic heated swimming pool.
9.8 53 reviews
Longboat Key, FL
16/07 – 21/07
327 €/nighttotal: 1635 € (5 )
Beach Castle Resort, Pool, Private Beach And Bayfront
2 2
apartment , Longboat Key
Beach Castle Resort, offering a pool, tennis court, and private beach access, is situated on Longboat Key, less than 1.6km from Longboat Key Beaches and Cannons Marina, with Jewfish Key approximately 5km away. This 66 square metre, one-bedroom waterfront apartment sleeps four, boasting a fully equipped kitchen, Smart TV, and access to on-site spa facilities, barbecue grills, and a garden.
9.2 80 reviews
Longboat Key, FL
14/07 – 16/07
316 €/nighttotal: 632 € (2 )
Relax At Gulf Silver Sands Resort #232, Longboat
1 4
apartment , Longboat Key
Silver Sands #232 Resort By Rva is situated on Longboat Key, just a 5-kilometre drive from Jewfish Key and Coquina Beach, offering easy access to the beautiful beaches of the area. This resort has received excellent user ratings, making it a popular choice for travellers. The apartment features one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy a range of amenities, including a swimming pool, tennis court, garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
9.5 133 reviews
Longboat Key, FL
27/06 – 04/07
136 €/nighttotal: 952 € (7 )
Palms Villa: Cozy & Minutes From Anna Maria Island
2 2
apartment , Bradenton
This two-bedroom apartment is situated in Shorewalk Vacation Villas, just a few kilometres from the beautiful beaches of Anna Maria Island and close to Bradenton's vibrant downtown. It has received excellent ratings for location, cleanliness, and user experience. The apartment covers 85 square metres and comfortably sleeps four guests. It includes a fully equipped kitchen, two bathrooms, and a range of amenities such as a swimming pool, jacuzzi, and tennis courts.
Frequently asked questions about holiday rentals in Longboat Key, FL
Which neighborhood in Longboat Key, FL should you consider for a vacation rental?
The most popular neighbourhood for vacation rentals is the south end of Longboat Key, as it's close to the beaches and restaurants. You can find a variety of options, from luxury condos to family-friendly homes.
What are the best Airbnb and holiday rentals in Longboat Key, FL?
What are the top family-friendly attractions in Longboat Key, FL?
Longboat Key is a great place for families, and the Mote Marine Laboratory & Aquarium is a must-visit. It's home to a variety of marine animals, including sharks, dolphins, and sea turtles. You can also enjoy the beach, or take a boat trip to see the local wildlife.
What are the most popular Airbnbs in Longboat Key, FL?
When is the best time to book a vacation rental in Longboat Key, FL?
The best time to book a vacation rental in Longboat Key is during the shoulder seasons, from April to May or September to October. The weather is still pleasant, but the crowds are smaller and the prices are lower.
What are the best holiday rentals with a pool in Longboat Key, FL?
What are the best budget-friendly activities in Longboat Key, FL?
Longboat Key is a great place to enjoy the outdoors on a budget. You can spend the day at the beach, go for a walk or bike ride along the Longboat Key Nature Trail, or take a picnic to the park. There are also plenty of free events held throughout the year, like the farmers market.
What are the best rentals for families and kids in Longboat Key, FL?
What are the best restaurants with local dishes in Longboat Key, FL?
There are several great restaurants in Longboat Key serving local dishes. The Shore restaurant is a popular spot for fresh seafood, and you can find a variety of other options, including Italian, Mexican, and American cuisine.
What are the best rentals or Airbnbs with a jacuzzi in Longboat Key, FL?
What are the best walking or cycling routes in Longboat Key, FL?
The Longboat Key Nature Trail is a great place for a walk or bike ride. It's a 6.5km paved trail that runs along the Gulf of Mexico. You can also enjoy the views from the Longboat Key Beach, or take a stroll along the Bayfront.
Are there pet-friendly attractions in Longboat Key, FL?
Longboat Key is a very pet-friendly place. Many of the beaches allow dogs, and there are several pet-friendly restaurants and shops. You can also take your dog for a walk or bike ride along the Longboat Key Nature Trail.
What are the benefits of choosing a vacation rental in Longboat Key, FL?
Vacation rentals offer more space and privacy than a hotel room. They also provide a more home-like experience, with a kitchen and laundry facilities. And you can often find rentals with great views and access to amenities like a pool or hot tub.
What are the top sports attractions and facilities in Longboat Key, FL?
Longboat Key is a great place for sports enthusiasts. There are several golf courses, including the Longboat Key Club, as well as tennis courts and a fitness centre. You can also enjoy a variety of water sports, such as swimming, kayaking, and paddleboarding.
Destinations nearby
Best Longboat Key, FL holiday rentals with a balcony
9.9 108 reviews
Longboat Key, FL
01/11 – 01/04
366 €/nighttotal: 55266 € (151 )
Pond-side 4br Oasis W/ Private Pool + Pickleball!
4 2
apartment , Bradenton
This spacious four-bedroom home is located in Bradenton, just a short distance from the lively downtown area and the River Walk, offering easy access to local attractions and cultural experiences. The property has received excellent ratings for its location, cleanliness, and overall user experience. The 204 square metre property comfortably accommodates up to 10 guests and comes equipped with a range of amenities including a private pool, a fully equipped kitchen, and a garden, perfect for families and groups looking for a relaxing and enjoyable stay.
9.0 1 review
Longboat Key, FL
20/07 – 22/07
465 €/nighttotal: 930 € (2 )
Silver Sands #242
1 1
house , Longboat Key
This Silver Sands #242 apartment in Longboat Key offers direct access to Longboat Key Beach and is situated 24 kilometres from the John and Mable Ringling Museum of Art. This property accommodates up to seven guests and features a well-equipped kitchen, air conditioning, a swimming pool, a terrace with sea views, and is conveniently located near cycling routes and 24 kilometres from Sarasota Bradenton International Airport.
9.9 136 reviews
Longboat Key, FL
08/10 – 12/10
441 €/nighttotal: 1764 € (4 )
Sea Grape Inn 6- Beachfront Property
2 6
apartment , Longboat Key
This beachfront apartment is situated on Longboat Key, within a 15-minute drive of The John and Mable Ringling Museum of Art and Sarasota Jungle Gardens. The property has received excellent ratings for location, cleanliness and user experience. The two-bedroom flat offers 102 square metres of space. Guests can enjoy a range of amenities, including a swimming pool, tennis court, and a fully equipped kitchen with a dishwasher.
Longboat Key, FL
01/11 – 01/04
382 €/nighttotal: 57682 € (151 )
Gorgeous 3-bedroom Beachfront Unit At Club Longboat!
3 2
apartment , Longboat Key
This three-bedroom flat at Iconic Club Longboat Beach and Tennis offers direct beach access and is situated a short distance from St. Armand's Circle, renowned for its upscale shopping and dining, and within easy reach of Sarasota's arts and culture scene, including the Asolo Theater and Van Wezel Performing Arts Centre. This remodelled developer's unit accommodates seven guests, featuring a balcony with gulf front views, updated furnishings, and access to on-site amenities such as eight Har-Tru tennis courts, two heated swimming pools, and a clubhouse, with a minimum 30-day stay ideal for extended getaways.
Best Longboat Key, FL holiday rentals with parking
9.6 47 reviews
Longboat Key, FL
27/06 – 04/07
171 €/nighttotal: 1197 € (7 )
Ck Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img
2 2
apartment , Bradenton
This apartment is situated on a lake in Bradenton, just 5km from IMG Academy, Smugglers Cove Adventure Golf, IMG Bollettieri Tennis Academy, IMG Soccer Academy, and State College of Florida. It has received excellent ratings for its location, cleanliness, and overall user experience. This 2-bedroom apartment can comfortably accommodate up to 4 guests and offers 116 square metres of living space. Amenities include a fully equipped kitchen, air conditioning, a private patio, a swimming pool, a jacuzzi, a spa, a tennis court, and parking.
9.8 31 reviews
Longboat Key, FL
10/10 – 17/10
222 €/nighttotal: 1554 € (7 )
Beautiful Beach Longboat Key Townhouse
2 4
apartment , Longboat Key
This Longboat Key holiday home, a seven-minute walk from Longboat Key's beaches and a fourteen-minute walk (0.8 km and 1.1 km respectively) from Cannons Marina, offers convenient access to local attractions. The 130-square-metre property boasts two bedrooms, three bathrooms, and sleeps six, featuring a swimming pool, on-site fitness centre, and watersports equipment, alongside a fully equipped kitchen and in-unit laundry facilities.
9.7 67 reviews
Longboat Key, FL
27/06 – 04/07
149 €/nighttotal: 1043 € (7 )
Banyan In Bradenton
1 2
apartment , Cortez
This one-bedroom apartment in Sunny Shores is conveniently located just 2 kilometres from the Florida Maritime Museum at Cortez and other attractions like H2O Watersportz and Anna Maria Sound. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 54 square metre apartment comfortably accommodates two guests and features a fully equipped kitchen, a washing machine, a private balcony and a television. You'll also have access to a fitness centre, concierge services, a garden and a spa, providing plenty of opportunities for relaxation and entertainment.
Longboat Key, FL
10/10 – 17/10
214 €/nighttotal: 1498 € (7 )
Silver Sands #234
1 4
house , Longboat Key
This beachfront property, Silver Sands #234, is situated in Longboat Key, offering direct access to the sand and is located 24 kilometres from the John and Mable Ringling Museum of Art. This holiday home accommodates up to seven guests and features air conditioning, a swimming pool, a terrace, a garden, a fitness centre, a tennis court, and private parking, with disabled facilities also available.