Holiday Rentals in Longboat Key, FL

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Longboat Key, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Longboat Key, FL

Search Coastal Holiday Rentals near Longboat Key, FL

Experience relaxing maritime culture at coastal holiday rentals in Longboat Key, FL, situated a short distance from popular beach communities.

Sun, Sand & Serenity  Beach Castle #17 - Longboat Key, FL
9.4 69 reviews

Sun, Sand & Serenity Beach Castle #17

apartment, Longboat Key
Beach Castle Resort #17 By Rva is a self-catering apartment located on Longboat Key, just 5km from Cannons Marina and 5km from Longboat Key Beaches. It has received excellent user ratings and is considered very good in terms of location, although the cleanliness rating is only OK.
The apartment is suitable for up to 4 guests and includes a bedroom, a bathroom, a fully equipped kitchen, a terrace, a garden and access to a swimming pool, a jacuzzi and a tennis court. Guests can also enjoy on-site parking, laundry facilities, and a DVD player.
Coastal Comfort - Beach Castle #23 By Rva - Longboat Key, FL
10 64 reviews

Coastal Comfort - Beach Castle #23 By Rva

apartment, Longboat Key
This waterfront apartment building is situated on Longboat Key, just 1.6 kilometres from Longboat Key Beaches and Cannons Marina, and 4.8 kilometres from Jewfish Key. It has received excellent ratings for location, cleanliness and overall user experience.
The apartment is on the ground floor and has one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a sofa bed, a TV with a DVD player, a spa tub, a terrace, access to a swimming pool, a jacuzzi, a tennis court, laundry facilities, barbecue grills, and parking.
Silver Sands #245a Resort By Rva - Longboat Key, FL
9.0 138 reviews

Silver Sands #245a Resort By Rva

apartment, Longboat Key
Silver Sands #245a Resort By Rva is situated on Longboat Key, just a short walk from the beach and Cannons Marina and within a 5km radius of Coquina Beach and Bradenton Beach, offering a peaceful escape in a tranquil setting. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience.
Each apartment is fully equipped with a kitchen, washing machine, and TV with a DVD player, providing a comfortable and convenient stay. Guests can enjoy a range of amenities, including a swimming pool, tennis court, garden, barbecue grills, and free Wi-Fi, ensuring a relaxing and enjoyable holiday.
Beach Front One Bedroom Condo Paradise. Ground Floor. - Longboat Key, FL
9.5 314 reviews

Beach Front One Bedroom Condo Paradise. Ground Floor.

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.

Best family friendly Longboat Key, FL holiday rentals

Among the 2233 accommodations in Longboat Key, FL, here are the 4 best family friendly rentals

Breathtaking Beach Front Property Ground Floor Condo - Longboat Key, FL
9.6 160 reviews

Breathtaking Beach Front Property Ground Floor Condo

apartment, Longboat Key
This apartment is situated on Longboat Key, just 0.3 kilometres from the beach and 3.2 kilometres from Cannons Marina, offering easy access to both the beach and local attractions. It has excellent user ratings, reflecting its popularity amongst previous guests.
The apartment is spacious, covering 102 square metres and accommodating up to 6 guests, with 2 bedrooms and 2 bathrooms. It offers a range of amenities, including a swimming pool, tennis court, and a garden with barbecue facilities, perfect for relaxing and enjoying the Florida sunshine.
Beachside Oasis At Runaway Bay 229 By Seabreeze Vacation - Longboat Key, FL
10 25 reviews

Beachside Oasis At Runaway Bay 229 By Seabreeze Vacation

apartment, Bradenton Beach
This beachfront flat in Bradenton Beach, Florida, is a short walk from Anna Maria Sound and less than 1.6km from the Bradenton Beach Marina and Bridge Street.
The two-bedroom, two-bathroom property sleeps six, boasts a fully equipped kitchen, in-unit laundry, private balcony, and access to a swimming pool, spa, fitness centre, and tennis court; nearby activities include watersports and visits to the Aluna Wellness Centre & Spa.
Poolside Condo · Waterslide & Games · Sleeps 6 - Longboat Key, FL
10 6 reviews

Poolside Condo · Waterslide & Games · Sleeps 6

apartment, South Bradenton
This two-bedroom condominium in Cedar Run Resort is situated in South Bradenton, offering convenient access within 16 to 24 kilometres to Downtown Bradenton, Anna Maria Island, and Downtown Sarasota, and just 10 kilometres to IMG Academy.
This family and dog-friendly holiday let accommodates up to six guests and features a fully equipped chef's kitchen, a screened-in porch, and access to community amenities including a heated swimming pool with a waterslide, putting green, and giant games.
Tides Inn On The Bay Vacation Homes - Longboat Key, FL
9.7 154 reviews

Tides Inn On The Bay Vacation Homes

house, Bradenton Beach
Tides Inn on the Bay Vacation Homes is located in Bradenton Beach, just a few steps from Cortez Beach and a 6-minute walk from the town centre, offering a peaceful yet convenient location. This property enjoys excellent ratings for cleanliness, location and user experience.
The self-catering accommodation offers comfortable amenities including a fully equipped kitchen, air conditioning, a private bathroom and a terrace or balcony. Guests can also enjoy a swimming pool, a garden, parking and a barbecue, and take advantage of the nearby fishing spots, airport shuttle service and access to other Bradenton Beach attractions.

Frequently asked questions about holiday rentals in Longboat Key, FL

  • What should a first-time visitor not miss in Longboat Key, FL?

    For a first-time visit, you should definitely check out St. Armands Circle. It's a charming shopping and dining district with a beautiful view of the bay. You can also take a stroll along the Longboat Key Beach, which is known for its white sand and clear waters.
  • What are the best Airbnb and holiday rentals in Longboat Key, FL?

  • Which neighborhood in Longboat Key, FL should you consider for a vacation rental?

    For a vacation rental, you might want to consider the south end of Longboat Key. It's quieter than the north end and has some lovely beaches. Many rentals have great views of the Gulf of Mexico.
  • What are the most popular Airbnbs in Longboat Key, FL?

  • What are the top family-friendly attractions in Longboat Key, FL?

    The Mote Marine Laboratory & Aquarium is a great place to visit with kids. They have interactive exhibits about marine life and even a touch tank. The Longboat Key Club is also a good option, with its golf course and swimming pool.
  • What are the best holiday rentals with a pool in Longboat Key, FL?

    Anna Maria Island Beach Palms 2b, Unit #212 Sand Cay Beach Resort Pool And Garden View and Tortuga #154 are the best holiday rentals with a pool 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 is during the shoulder seasons, from April to May and September to October. You'll get better rates and fewer crowds compared to the peak season.
  • What are the best rentals for families and kids in Longboat Key, FL?

  • What are the best budget-friendly activities in Longboat Key, FL?

    A nice way to spend a day is by taking a walk or bike ride along the Longboat Key Beach. You can also explore the many parks and nature trails in the area, like the Bayfront Park or the Longboat Key Nature Center.
  • What are the best rentals or Airbnbs with a jacuzzi in Longboat Key, FL?

  • What are the best restaurants with local dishes in Longboat Key, FL?

    For local dishes, try Harry's Continental Kitchens or The Chart Room. These restaurants offer classic Florida cuisine with fresh seafood and local ingredients.
  • What are the best walking or cycling routes in Longboat Key, FL?

    The Longboat Key Bike Trail is a popular route for cyclists, stretching along the coast. For walkers, the Gulf of Mexico Drive offers beautiful views of the beach and the Gulf.
  • Are there pet-friendly attractions in Longboat Key, FL?

    Yes, there are several pet-friendly beaches in Longboat Key, such as the Longboat Key Beach. You can also find dog-friendly restaurants and shops in the area.
  • What are the benefits of choosing a vacation rental in Longboat Key, FL?

    Vacation rentals offer more space and privacy compared to hotels. They're also a great option for families or groups of friends travelling together.
  • What are the top sports attractions and facilities in Longboat Key, FL?

    Longboat Key is known for its golf courses, with the Longboat Key Club being a popular option. There are also public tennis courts available for use.

Popular destinations

Top Holiday Rentals with a Pool in Longboat Key, FL

Our holiday rentals near the water in Longboat Key, FL include a pool, so a relaxing swim is always on the cards.

Longbeach #12 - Longboat Key, FL
10 2 reviews

Longbeach #12

apartment, Longboat Key
This two-bedroom, two-bathroom condominium in Longboat Key is situated centrally, offering convenient access within 100 metres of the beach, shops, and restaurants.
This ground-floor apartment accommodates up to six guests and features air conditioning, internet, a kitchen, a swimming pool, and parking, with direct access to a pool and an expansive grass area.
Country Club Long Boat Key Beach Villa  2b 3ba Pool - Longboat Key, FL
9.8 99 reviews

Country Club Long Boat Key Beach Villa 2b 3ba Pool

apartment, Longboat Key
This Longboat Key townhouse, situated a short distance from a private bay beach and eight minutes' drive (approximately 13km) from St. Armand's Circle, offers easy access to Anna Maria Island and Sarasota.
The three-storey property boasts two bedrooms, three bathrooms, and accommodates up to six guests, featuring a private enclosed garage, screened lanai, full-size washer/dryer, and access to a swimming pool, Jacuzzi, tennis court, and spa.
Sun Salt Sand: Summer Discounts! - Longboat Key, FL
10 72 reviews

Sun Salt Sand: Summer Discounts!

apartment, Longboat Key
This beachfront Longboat Key apartment, situated on Gulf of Mexico Drive, offers direct beach access and is conveniently located near mid-island amenities.
The one-bedroom, one-bathroom condo sleeps four, features a fully equipped kitchen with granite countertops and stainless steel appliances, a private lanai with sunset views, and includes amenities such as beach chairs, an umbrella, and a Pack 'N Play.
Silver Sands #234 - Longboat Key, FL
No reviews

Silver Sands #234

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.

Choose the Right Self-Catering Rentals with Parking in Longboat Key, FL

Free on-site parking comes with these holiday rentals near the water in Longboat Key, FL, letting you focus on the coast and local beaches.

Charming 2-bedroom Condo Overlooking Sarasota Bay On Longboat Key - Longboat Key, FL
10 1 review

Charming 2-bedroom Condo Overlooking Sarasota Bay On Longboat Key

apartment, Longboat Key
This Longboat Key condominium offers a prime location, situated a mere 5 kilometers from St. Armands Circle and 12 kilometers from the Mall at University Town Centre, with direct access to Longboat Key Beaches and Bradenton Beach.
This two-bedroom, two-bathroom apartment comfortably accommodates four guests and features a private gulf beach access across the street, two heated swimming pools, an on-site fitness room, and a BBQ area, with kayaking, motor boating, and sailing readily available nearby.
Sun, Sand & Silver Sands  Gulfside Resort #237 By Rva - Longboat Key, FL
9.2 460 reviews

Sun, Sand & Silver Sands Gulfside Resort #237 By Rva

apartment, Longboat Key
Silver Sands #237 Resort By Rva is situated on Longboat Key, a short walk from Longboat Key Beaches and Cannons Marina, and within a 3-mile drive of Jewfish Key and Coquina Beach. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
This apartment complex provides direct beach access, allowing guests to easily enjoy the beautiful white sands and turquoise waters of Longboat Key. The resort offers a range of amenities, including a swimming pool, tennis court, and a garden with barbecue grills.
Poolside Peace  Silver Sands Resort #242 By Rva - Longboat Key, FL
9.2 77 reviews

Poolside Peace Silver Sands Resort #242 By Rva

apartment, Longboat Key
Silver Sands #242 Resort By Rva is a beachfront apartment on Longboat Key, just a 10-minute walk from the beach and Cannons Marina, and within 5 km of Coquina Beach and Bradenton Beach. The apartment has excellent user ratings and is rated very good for cleanliness.
The apartment has one bedroom and one bathroom, and can accommodate up to four guests. It includes a fully-equipped kitchen, a terrace, a garden, a swimming pool, a tennis court, free Wi-Fi and parking.
Walk To Beach And Cedar East Club Amenities - Pool - Longboat Key, FL
10 2 reviews

Walk To Beach And Cedar East Club Amenities - Pool

apartment, Longboat Key
This Longboat Key duplex offers a prime location, just seconds from deeded beach access and a short walk to local cafes, boutiques, and bayfront paths, with Joan M. Durante Park 483 metres away.
This dog-friendly (for pets under 25 lbs) two-bedroom, two-bathroom holiday home accommodates up to six guests and features a private screened lanai, direct master bedroom patio access, and use of Cedars East Club amenities including a swimming pool, tennis courts, and a fitness centre.

Check Out Luxury Holiday Rentals in Longboat Key, FL

Staying in a luxury holiday rental or Airbnb in Longboat Key, FL ensures every detail of your trip feels considered, with high-end finishes and prime locations.

Tarawitt Home - Longboat Key, FL
No reviews

Tarawitt Home

house, Longboat Key

Best Longboat Key, FL holiday rentals with a balcony

On The Beach, 2nd Floor, Elevator, Heated Swimming Pool And Spa, Freshly Painted - Longboat Key, FL
9.0 13 reviews

On The Beach, 2nd Floor, Elevator, Heated Swimming Pool And Spa, Freshly Painted

apartment, Longboat Key
Cedars East 2br Condo  Unit #611 By Rva - Longboat Key, FL
10 1 review

Cedars East 2br Condo Unit #611 By Rva

apartment, Longboat Key
Beach Castle Resort #24 - Longboat Key, FL
10 1 review

Beach Castle Resort #24

house, Longboat Key
Comfy Florida Condo Near Beach In Bradenton Florida - Longboat Key, FL
9.5 41 reviews

Comfy Florida Condo Near Beach In Bradenton Florida

apartment, Bradenton

Best Pet-Friendly Holiday Rentals in Longboat Key, FL

The dog-friendly holiday rentals below in Longboat Key, FL feature outdoor wash stations and easy access to pet-welcoming beaches.

Bradenton, Fl Waterfront
 Getaway - Longboat Key, FL
9.3 3 reviews

Bradenton, Fl Waterfront Getaway

apartment, Bayshore Gardens
2bed 2 Bath Sleeps 6. Walk To The Water, Less Than A Mile To Anna Maria Island - Longboat Key, FL
9.8 11 reviews

2bed 2 Bath Sleeps 6. Walk To The Water, Less Than A Mile To Anna Maria Island

apartment, Cortez
Seabreeze B · Pet-friendly · Heated Pool - Longboat Key, FL
9.4 33 reviews

Seabreeze B · Pet-friendly · Heated Pool

apartment, Holmes Beach
2br At Lecom Park Downtown Beaches & Ample Parking Space - Longboat Key, FL
8.7 33 reviews

2br At Lecom Park Downtown Beaches & Ample Parking Space

apartment, Bradenton

Popular Self-Catering Holiday Rentals with a Jacuzzi in Longboat Key, FL

These holiday rentals near the water in Longboat Key, FL come with a hot tub or jacuzzi, ideal for a private evening soak. Explore now.

Shorewalk 205 - Bradenton-  The Palms Condo 2 Bedroom / 2 Bath,  5 Miles From  Anna Maria Island And Near Img, Maximum Occupancy Of 4 People. - Longboat Key, FL
8.2 30 reviews

Shorewalk 205 - Bradenton- The Palms Condo 2 Bedroom / 2 Bath, 5 Miles From Anna Maria Island And Near Img, Maximum Occupancy Of 4 People.

apartment, Bradenton
Jd Shorewalk, Pools, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Longboat Key, FL
9.5 22 reviews

Jd Shorewalk, Pools, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img

apartment, Bradenton
2/2 Condo Beach View, Pool, Fitness, Tennis - Longboat Key, FL
No reviews

2/2 Condo Beach View, Pool, Fitness, Tennis

apartment, Longboat Key
*Casa Mia* Fabulous 2br Condo W/2pools, Mins To Img/beach/anna Maria Isl - Longboat Key, FL
9.9 371 reviews

*Casa Mia* Fabulous 2br Condo W/2pools, Mins To Img/beach/anna Maria Isl

apartment, Bradenton

Top-Rated Holiday Rentals with a Spa in Longboat Key, FL

After enjoying everything Longboat Key, FL has to offer, a spa session at your holiday rental is the ideal way to finish the day.

Sf Shorewalk, Pools, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img - Longboat Key, FL
9.8 78 reviews

Sf Shorewalk, Pools, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img

apartment, Bradenton
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