Holiday Rentals in Longboat Key

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Longboat Key holiday rentals
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Longboat Key holiday rentals: compare the best deals

Best family friendly Longboat Key holiday rentals

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

Pet-friendly Cedars East Unit 847 By Rva - Longboat Key
9.5 14 reviews

Pet-friendly Cedars East Unit 847 By Rva

apartment, Longboat Key
This Longboat Key holiday home is situated just 1.6 kilometres from Longboat Key Beaches and 4.8 kilometres from Cannons Marina, offering a peaceful and convenient location for exploring the area. It has received excellent user ratings, making it a popular choice for travellers.
This two-bedroom property spans 134 square metres and offers a comfortable and spacious layout. Enjoy amenities such as a swimming pool, garden, fitness centre and fully equipped kitchen, as well as the convenience of parking and internet access.
Beach Castle Resort, Pool, Private Beach And Bayfront - Longboat Key
9.8 54 reviews

Beach Castle Resort, Pool, Private Beach And Bayfront

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.
Fully Remodeled Pool Home Less Than 5 Miles To Beach Home - Longboat Key
9.8 143 reviews

Fully Remodeled Pool Home Less Than 5 Miles To Beach Home

house, Bradenton
This Bradenton property is conveniently located just a short distance from Arcadeland and IMG Academy, making it ideal for families seeking entertainment or sports enthusiasts. The home has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
This three-bedroom house offers a range of amenities including a swimming pool, spa, and restaurant, providing plenty of opportunities for relaxation and recreation. The property also features free Wi-Fi, a fully equipped kitchen, a washing machine, and barbecue facilities, allowing guests to enjoy a self-catering experience.
Resort Condo · Heated Pool W/ Slide · Near Beaches - Longboat Key
9.2 5 reviews

Resort Condo · Heated Pool W/ Slide · Near Beaches

apartment, South Bradenton
This two-bedroom condominium in Cedar Run Resort, South Bradenton, is situated within a 1.6 to 2.4 kilometre drive of Downtown Bradenton, Anna Maria Island, and Sarasota, and a 0.9 kilometre drive to IMG Academy.
This family and dog-friendly apartment offers capacity for six guests, featuring a resort-style heated swimming pool with a water slide, putt-putt golf, and a range of games, alongside in-unit laundry facilities and provided beach essentials.

Best Longboat Key holiday rentals with a pool

Among the 2233 accommodations in Longboat Key, here are the 4 best rentals with a pool

Beach Front One Bedroom Condo Paradise. Ground Floor. - Longboat Key
9.5 315 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.
Gulf Views  Silver Sands #250, Longboat Key By Rva - Longboat Key
9.0 81 reviews

Gulf Views Silver Sands #250, Longboat Key By Rva

apartment, Longboat Key
Silver Sands #250 Resort By Rva is a beachfront apartment situated on Longboat Key, a short walk from Longboat Key Beaches and Cannons Marina, offering a peaceful and convenient location. It has consistently received excellent ratings for its location, cleanliness and overall user experience.
The apartment is suitable for up to four guests and features a fully equipped kitchen, a TV with a DVD player, a washing machine and a sofa bed. Guests can enjoy a range of amenities including a swimming pool, tennis court, garden, barbecue grills and free Wi-Fi in public areas.
Just Beachy - Longboat Key
8.0 1 review

Just Beachy

apartment, Longboat Key
Just Beachy, a beachfront property on Longboat Key, Florida, is situated 22.5 kilometres from the Ringling Museum of Art and 21 kilometres from Sarasota Jungle Gardens.
This two-bedroom, two-bathroom holiday home boasts 94 square metres of living space, accommodating up to 11 guests and featuring a private pool, Jacuzzi, and balcony with stunning ocean views; free parking is also provided.
Paradise Palms - Chic Prime Spot W Pool - Longboat Key
8.2 40 reviews

Paradise Palms - Chic Prime Spot W Pool

house, Bradenton
This Bradenton holiday home, Paradise Palms, enjoys a convenient location near Palma Sola Causeway Park, an 8-minute walk away, and is within easy driving distance (approximately 10km) of Anna Maria City Pier and 22km from The John and Mable Ringling Museum of Art.
The 88 square metre property offers two bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, garden, fully equipped kitchen with dishwasher, free Wi-Fi, and air conditioning.

Frequently asked questions about holiday rentals in Longboat Key

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

    You definitely shouldn't miss a stroll along the beautiful white sands of Longboat Key Beach. The sunsets are spectacular, and there's a great view of the Gulf of Mexico. You can also visit the Mote Marine Laboratory & Aquarium, which is a great place to learn about marine life and see some fascinating creatures.
  • What are the best Airbnb and vacation rentals in Longboat Key?

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

    For a quieter, more residential feel, try the north end of Longboat Key around the area of Bay Isles. It's close to the beach and has some lovely parks and nature trails. If you prefer to be closer to the shops and restaurants, then the south end around the area of Longboat Key Club is a good choice.
  • What are the most popular Airbnbs in Longboat Key?

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

    The Longboat Key Beach is a great place for families, with plenty of space for kids to run around and build sandcastles. The Mote Marine Laboratory & Aquarium is also a big hit with families, especially the kids, with interactive exhibits and fascinating marine life.
  • What are the best vacation rentals with a pool in Longboat Key?

  • 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 and September to October. The weather is still pleasant, and the crowds are smaller, making it a more relaxed experience. You'll also find better deals on rentals during these months.
  • What are the best rentals for families and kids in Longboat Key?

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

    You can enjoy a free walk or bike ride along the Longboat Key Beach. There are also several free public parks and nature trails on the island, where you can enjoy the scenery and fresh air. The Longboat Key Public Library is a great place to relax and read, and they often host free events and workshops.
  • What are the best rentals or Airbnbs with a jacuzzi in Longboat Key?

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

    For a taste of local seafood, try The Beach House Restaurant on the south end of the island. They have a great view of the Gulf of Mexico and serve fresh, local seafood dishes. Another good option is Harry's Continental Kitchens, which has been a local favourite for years and offers a variety of dishes, including fresh seafood and pasta.
  • What are the best walking or cycling routes in Longboat Key, FL?

    The Longboat Key Beach is a great place for a walk or bike ride, with stunning views of the Gulf of Mexico. You can also try the Longboat Key Nature Trail, which winds its way through a beautiful mangrove forest and offers a glimpse into the island's natural beauty.
  • Are there pet-friendly attractions in Longboat Key, FL?

    Many of the beaches in Longboat Key are dog-friendly, but it's best to check with the specific beach before you go. The Longboat Key Nature Trail is also a great place to take your furry friend for a walk, as long as they are on a leash.
  • What are the benefits of choosing a vacation rental in Longboat Key, FL?

    Vacation rentals in Longboat Key offer more space and privacy than a hotel room, and they often come with amenities like a private pool and a fully equipped kitchen. This can be a great option for families or groups of friends who want to enjoy a more relaxed and comfortable vacation.
  • What are the top sports attractions and facilities in Longboat Key, FL?

    Longboat Key is a great place for outdoor enthusiasts. The Longboat Key Club has a championship golf course, tennis courts, and a fitness centre. You can also enjoy swimming, kayaking, and paddleboarding in the Gulf of Mexico.

Popular destinations

Best Longboat Key holiday rentals with a balcony

Resort Condo W/ Beach Access On Anna Maria Island! - Longboat Key
9.3 33 reviews

Resort Condo W/ Beach Access On Anna Maria Island!

house, Bradenton Beach
This two-bedroom apartment is situated in Bradenton Beach, just a short walk from Cortez Beach and a 24km drive from The John and Mable Ringling Museum of Art.
The 100 square metre property boasts a private balcony with sea views, a fully equipped kitchen and a shared swimming pool, ideal for families or small groups seeking a beachfront stay.
Resort Retreat W/ Pools! 6 Mi To Bradenton Beach - Longboat Key
No reviews

Resort Retreat W/ Pools! 6 Mi To Bradenton Beach

house, Bradenton
This detached house in Bradenton is situated approximately 9.6 kilometres from Bradenton Beach, with the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art both within 12.8 kilometres.
This 109 square metre accommodation offers a private patio, air conditioning, a fully equipped kitchen with a dishwasher, and an outdoor swimming pool and hot tub, comfortably accommodating up to nine guests.
Home With Heated Pool, Spa, Games, Walk To Beach - Longboat Key
9.8 93 reviews

Home With Heated Pool, Spa, Games, Walk To Beach

apartment, Holmes Beach
This two-bedroom apartment is situated in Holmes Beach, just under a kilometre from Holmes Beach Beaches and Bradenton Beach.
The property offers a fully equipped kitchen, a private balcony, a swimming pool, and a spa, ideal for families or groups of up to six people.
Silver Sands #251 - Longboat Key
10 1 review

Silver Sands #251

house, Longboat Key
This beachfront villa, Silver Sands #251, 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 7 guests and features a well-equipped kitchen, air conditioning, a swimming pool, a terrace with sea views, and complimentary WiFi, with facilities for disabled guests and proximity to cycling routes.

Best Longboat Key holiday rentals with parking

Silver Sands #246 - Longboat Key
9.5 2 reviews

Silver Sands #246

house, Longboat Key
Silver Sands #246 is a beachfront villa in Longboat Key, just steps from Longboat Key Beach and approximately 24 kilometres from the John and Mable Ringling Museum of Art.
This villa accommodates up to seven guests and features direct beach access, a well-equipped kitchen with a dishwasher, microwave, and oven, complimentary WiFi, air conditioning, a swimming pool, a fitness centre, tennis courts, and private parking, with facilities for disabled guests also available.
Laplaya 102e-tropical Garden View Near The Pool! - Longboat Key
10 10 reviews

Laplaya 102e-tropical Garden View Near The Pool!

apartment, Longboat Key
This beachfront apartment is situated on Longboat Key, just 8 kilometres from the John and Mable Ringling Museum of Art and the Van Wezel Performing Arts Hall, offering a peaceful retreat close to cultural attractions. The apartment consistently receives very good ratings for cleanliness, location, and overall user experience.
The apartment features two bedrooms and one bathroom, spanning 65 square metres. Guests can enjoy a fully equipped kitchen, a washing machine, a swimming pool, a garden, and an outdoor dining area, making it perfect for a relaxing and comfortable stay.
Silver Sands #232 - Longboat Key
10 1 review

Silver Sands #232

house, Longboat Key
Silver Sands #232 is a beachfront property located in Longboat Key, offering direct access to the beach and situated 24 kilometres from the John and Mable Ringling Museum of Art.
This holiday home accommodates up to seven guests and features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a fitness centre, a tennis court, and free private parking with complimentary WiFi.
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027 - Longboat Key
9.8 268 reviews

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

apartment, Longboat Key
This apartment is located on Longboat Key, just 3 kilometres from Coquina Beach and Bradenton Beach, and a 10-minute walk from Longboat Key Beaches and Cannons Marina. This property has received excellent user ratings and is perfect for families or groups of friends seeking a relaxing getaway.
The apartment has two bedrooms and two bathrooms and is 92 square metres in size. It offers a fully equipped kitchen, a fireplace, a balcony, a swimming pool, and a spa, as well as parking and internet access.
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