Longboat Key holiday rentals: compare the best deals
Longboat Key
08/20 – 08/22
HK$2562/nightTotal: HK$5124 (2 )
Silver Sands #251a
1 2
house , Longboat Key
This beachfront 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 and 27 kilometres from the Sarasota International Convention Centre. This accommodation for three guests features a kitchen with a fridge and microwave, air conditioning, a swimming pool, a balcony, a fitness centre, a tennis court, and parking, with free Wi-Fi and facilities for guests with disabilities.
9.4 52 reviews
Longboat Key
07/11 – 07/17
HK$2635/nightTotal: HK$15810 (6 )
Beautiful Canal Front Unit!see Manatees Playing From Your Living Room.cabana #12
1 3
apartment , Longboat Key
This Longboat Key apartment is situated just a short walk from a convenience store and a selection of restaurants, directly across the street from a heated pool and laundry facilities. It boasts an excellent user rating, indicating a high level of satisfaction from previous guests. The apartment is a comfortable one-bedroom property with a floor area of 62 square metres and a capacity of up to four guests. It offers a well-equipped kitchen, a private porch overlooking the bay, and easy access to the beach, local attractions, and water activities.
9.0 36 reviews
Longboat Key
07/01 – 07/05
HK$4112/nightTotal: HK$16448 (4 )
Pet Friendly Tropical Home W/pool And Grill!
3 8
apartment , Bradenton
This three-bedroom home is conveniently located in Northwest Bradenton, just a short drive from the beaches of Anna Maria Island, Bradenton Beach, and Holmes Beach, as well as Lakewood Ranch, Sarasota, and Tampa. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. This spacious property spans 177 square metres and can comfortably accommodate up to eight guests. The apartment boasts a private pool, a modern coastal design, two living rooms, a fully equipped kitchen, and a range of outdoor amenities, including a grill and a large horseshoe driveway.
10 4 reviews
Longboat Key
07/01 – 07/05
HK$2972/nightTotal: HK$11888 (4 )
Sleeps 8 - Pool W/ Slide - Games - 6 Min To Img
2 8
apartment , South Bradenton
This 2-bedroom flat in Cedar Run Resort, South Bradenton, offers convenient access, being a 10-15 minute drive from Downtown Bradenton, Anna Maria Island, and Sarasota, and just a 6-minute drive to IMG Academy. This family and dog-friendly condo accommodates up to 8 guests and features a chef's kitchen with high-end appliances, a private screened porch, and access to resort amenities including a heated swimming pool with a waterslide, putting green, and cornhole, along with provided beach essentials.
9.8 93 reviews
Longboat Key
10/10 – 10/17
HK$1830/nightTotal: HK$12810 (7 )
Country Club Long Boat Key Beach Villa 2b 3ba Pool
2 4
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.
Longboat Key
08/20 – 08/21
HK$3903/nightfor 1 night
Silver Sands #232
1 2
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.
9.8 83 reviews
Longboat Key
07/11 – 07/17
HK$1102/nightTotal: HK$6612 (6 )
Stay & Play - 4 Min From Img
1 3
apartment , Bayshore Gardens
This Bayshore Gardens self-catering property is conveniently located a short drive from Sarasota-Bradenton International Airport (SRQ) and popular attractions including Anna Maria Island, IMG Academy, and Siesta Key beach. The one-bedroom duplex apartment sleeps three, boasting a fully equipped kitchen, private garden with fire pit and grill, and complimentary parking; a queen-size bed and pull-out sofa provide comfortable accommodation.
9.2 51 reviews
Longboat Key
07/11 – 07/17
HK$2322/nightTotal: HK$13932 (6 )
Lazy Livin 6 · Pool 50 Ft Away · 2-min Beach
2 3
apartment , Bradenton Beach
This smoke-free apartment is located in Bradenton Beach, just a few steps from the beach and within 1.6 kilometres of Anna Maria Sound and Bradenton Beach Marina. The apartment has received excellent ratings from previous guests for its location, cleanliness, and overall experience. The apartment is a 2-bedroom, 1-bathroom property with a floor area of 60 square metres and can comfortably accommodate up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, and parking, along with access to a water park, barbecue grills, and a nearby spa.
9.5 41 reviews
Longboat Key
07/11 – 07/17
HK$1638/nightTotal: HK$9828 (6 )
Comfy Florida Condo Near Beach In Bradenton Florida
2 3
apartment , South Bradenton
This two-bedroom apartment is located just 0.9 kilometres from Arcadeland and 1.6 kilometres from IMG Academy, making it ideal for families and groups visiting South Bradenton. The property has received excellent ratings for its cleanliness, location and overall user experience. The apartment is suitable for up to four guests and offers a comfortable layout with two bathrooms. Enjoy access to a range of amenities including a swimming pool, a fitness centre, a jacuzzi, and a garden, perfect for a relaxing and enjoyable stay.
9.6 28 reviews
Longboat Key
07/15 – 07/24
HK$3867/nightTotal: HK$34803 (9 )
Unit #312 Sand Cay Beach Resort Pool View
2 6
apartment , Longboat Key
This two-bedroom apartment is situated on Longboat Key, just 0.3 kilometres from the beach and 3.2 kilometres from Cannons Marina. The apartment boasts a fully equipped kitchen, a private balcony, and access to a swimming pool, tennis court, and garden, making it ideal for families or groups of up to six guests.
9.6 58 reviews
Longboat Key
07/15 – 07/24
HK$3081/nightTotal: HK$27729 (9 )
The Palms #3 Beach, Pool & Trolley No Car Needed
2 6
apartment , Holmes Beach
This holiday home is located in Holmes Beach, just under a kilometre from Bradenton Beach, Anna Maria Sound, and AMI Paddleboard Adventures, offering easy access to the area's many attractions. The property has consistently received excellent user ratings for its location, cleanliness, and overall experience. The two-bedroom house spans 70 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a private swimming pool, a spa, a garden, and a terrace, providing everything you need for a relaxing and enjoyable stay.
9.4 18 reviews
Longboat Key
08/20 – 08/22
HK$2236/nightTotal: HK$4472 (2 )
Charming Longboat Key Bungalow Minutes From Beaches, Restaurants, Parks
1 2
apartment , Longboat Key
This Longboat Key apartment, less than 1.6km from Longboat Key's beaches and Cannons Marina, and 4.3km from Jewfish Key, offers convenient access to water activities and local attractions. The 48-square-metre one-bedroom flat sleeps two, includes a fully equipped kitchen with laundry facilities, a patio, and modern amenities such as a Smart TV, and is situated in a smoke-free building with barbecue grills.
Best family friendly Longboat Key holiday rentals
Among the 1669 accommodations in Longboat Key, here are the 4 best family friendly rentals
9.3 75 reviews
Longboat Key
07/01 – 07/08
HK$2388/nightTotal: HK$16716 (7 )
Coquina Beach Club 110
1 2
studio , Bradenton Beach
This studio apartment is located in Bradenton Beach, just a short walk from the beach and 2.1km from Cortez Beach, offering a peaceful and convenient location for exploring the area. The studio has received excellent user ratings for its location, cleanliness, and overall experience. The self-catering studio spans 51 square meters and comfortably accommodates two guests. It features a fully equipped kitchen, a private balcony, and access to a shared swimming pool, spa, and garden, providing everything you need for a relaxing and enjoyable stay.
10 1 review
Longboat Key
07/11 – 07/17
HK$3131/nightTotal: HK$18786 (6 )
Inn On The Beach 7304 By Fvc
1 3
apartment , Longboat Key
This Longboat Key apartment boasts an oceanfront location, less than 1.6km from the Islandside Golf Course and Mote Marine Laboratory & Aquarium, and within 4.8km of Lido Beach and St Armands Circle. The 60-square-metre flat offers one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, jacuzzi, and spa.
9.9 37 reviews
Longboat Key
07/11 – 07/17
HK$2192/nightTotal: HK$13152 (6 )
The Coastal Nest • Private Pool & Backyard
1 3
apartment , South Bradenton
This South Bradenton duplex, a 20-minute (32km) drive from Bradenton Beach and 5 minutes (8km) from local amenities, offers a convenient coastal location. Sleeping up to 7 guests, this three-bedroom, two-bathroom property boasts a private heated pool, fenced backyard, fully equipped kitchen, smart TV, Wi-Fi, washer/dryer, driveway parking, and keypad entry.
9.6 74 reviews
Longboat Key
07/01 – 07/05
HK$4867/nightTotal: HK$19468 (4 )
Private Heated Pool Home W/arcade Games 15 Min To Beach!
3 8
apartment , Bradenton
This charming house is situated in Bradenton, just 2.7km from Palma Sola Causeway Park, 18km from the Ringling Museum of Art, and 48km from Tropicana Field. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience. The three-bedroom home spans 153 square metres and comfortably accommodates up to 10 guests. Enjoy a private pool, free parking, a fully equipped kitchen, air conditioning, and free Wi-Fi, making it the perfect base for exploring Bradenton and its surrounding attractions.
Best Longboat Key holiday rentals with a pool
Among the 1669 accommodations in Longboat Key, here are the 4 best rentals with a pool
9.9 43 reviews
Longboat Key
07/01 – 07/05
HK$4461/nightTotal: HK$17844 (4 )
Nautical Escape! Private Pool Home With A Tropical Backyard Oasis!
4 8
apartment , West Bradenton
This West Bradenton holiday home enjoys a convenient location, approximately 16 kilometres from Sarasota Bradenton International Airport and 19 kilometres from The John and Mable Ringling Museum of Art, offering easy access to beaches and a boat ramp. The four-bedroom property boasts a private pool, free Wi-Fi, a fully equipped kitchen, and free private parking, comfortably accommodating families or groups and providing all the amenities needed for a relaxing West Bradenton getaway.
9.7 257 reviews
Longboat Key
07/15 – 07/24
HK$2369/nightTotal: HK$21321 (9 )
Backyard Oasis New Pool Tiki Bar Near Img
1 6
apartment , Bayshore Gardens
This Bayshore Gardens house, located 8km from Sarasota-Bradenton International Airport and 5 minutes from IMG Academy, offers easy access to beaches and the city centres of Bradenton and Sarasota. Sleeping up to 16 guests, this completely renovated four-bedroom, two-bathroom property boasts a spacious open-plan layout, a saltwater heated pool with Tiki bar, large fenced garden with gas BBQ, and high-speed WiFi; all within a short driving distance of local attractions.
9.5 133 reviews
Longboat Key
06/27 – 07/04
HK$1229/nightTotal: HK$8603 (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.
10 107 reviews
Longboat Key
08/20 – 08/22
HK$3088/nightTotal: HK$6176 (2 )
Sandy Toes And Sun Kissed Nose!
1 2
apartment , Longboat Key
This ground-floor studio apartment boasts a prime Longboat Key location directly on the Gulf of Mexico, offering immediate beach access and proximity to the heated swimming pool. The self-catering apartment sleeps four guests and features a fully equipped kitchen, private lanai, and access to on-site amenities including BBQ facilities and laundry, plus a Pack 'N Play cot for infants.
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.
Destinations nearby
Best Longboat Key holiday rentals with a balcony
9.8 58 reviews
Longboat Key
07/01 – 07/08
HK$1460/nightTotal: HK$10220 (7 )
Luxury Lakefront Condo, Resort Amenities, 10 Minutes To Beach
2 2
apartment , Bradenton
This lakefront apartment is located in the Shorewalk Resort Complex in Bradenton, just 16 kilometres from the Gulf of Mexico and within easy walking distance of restaurants, shops, and a cinema. It has received excellent user ratings and is a great option for those seeking a relaxing and enjoyable stay. The apartment is 116 square metres in size and can comfortably accommodate up to four guests. It offers a range of amenities and activities including a swimming pool, jacuzzi, tennis court, and free equipment rental for activities like tennis, basketball, ping pong, and fishing.
10 1 review
Longboat Key
08/20 – 08/21
HK$6319/nightfor 1 night
Silver Sands #238
1 2
house , Longboat Key
This holiday home, Silver Sands #238, is located in Longboat Key, just 200 metres from Longboat Key Beach and 24 kilometres from the John and Mable Ringling Museum of Art. This air-conditioned property offers accommodation for 15 guests with 3 bedrooms, a living room, a fully equipped kitchen, a balcony, an outdoor dining area, a children's playground, a fitness room, on-site cycling, a garden, and free private parking with complimentary WiFi.
9.2 7 reviews
Longboat Key
07/11 – 07/17
HK$1585/nightTotal: HK$9510 (6 )
Ab Shorewalk -Pool, Tennis, Pickle Ball, Near Beaches Anna Maria Island And Img
2 3
apartment , Bradenton
This Bradenton lakeside apartment, five minutes from IMG Academy and fifteen minutes (approx. 24km) from Anna Maria Island and Longboat Key beaches, offers convenient access to local attractions. The 109 square metre, two-bedroom, two-bathroom property sleeps four guests and boasts a private terrace, swimming pool, Jacuzzi, and tennis court, alongside a fully equipped kitchen and air conditioning.
9.2 28 reviews
Longboat Key
07/20 – 07/22
HK$1925/nightTotal: HK$3850 (2 )
Mycataleya Comfy Condo Near Beach (Bradenton)
2 1
apartment , Bradenton
This Bradenton apartment is conveniently located just 10 kilometres from Sarasota Bradenton International Airport and 13.7 kilometres from the John and Mable Ringling Museum of Art. The 100 square metre property boasts two bedrooms, two bathrooms, sleeps seven guests, and features a private balcony with river views, a full kitchen, and access to on-site amenities including a swimming pool, hot tub, tennis court, and table tennis.
Best Longboat Key holiday rentals with parking
9.5 65 reviews
Longboat Key
07/15 – 07/24
HK$3456/nightTotal: HK$31104 (9 )
Sand Dollar Beach Side Villa
2 6
house , Holmes Beach
This charming two-bedroom villa is located in Holmes Beach, just steps from the beautiful beaches of Anna Maria Island, an 8-minute walk from the town centre, and a short drive from Bradenton Beach. The property has received excellent ratings for its location, cleanliness, and overall user experience. The 81 square metre villa comfortably accommodates up to six guests and features a fully equipped kitchen, a relaxing patio, and a private swimming pool. Guests can enjoy free Wi-Fi, air conditioning, and private parking, as well as access to a spa and a garden.
9.5 1698 reviews
Longboat Key
07/15 – 07/24
HK$2159/nightTotal: HK$19431 (9 )
Anna Maria Island Beach Palms 2b
2 6
apartment , Bradenton Beach
This Bradenton Beach apartment is situated just a stone's throw from the beach and within easy reach of attractions like Cortez Beach and Coquina Beach. The apartment has received excellent ratings for its location, cleanliness and overall user experience. The apartment is perfect for families or groups, offering a comfortable space with a well-equipped kitchen, a private heated pool, and a children's playground. Guests can enjoy a range of amenities, including a fitness centre, tennis court, spa, restaurant and bar, as well as direct access to the beach.
9.2 80 reviews
Longboat Key
10/10 – 10/17
HK$1965/nightTotal: HK$13755 (7 )
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.
Longboat Key
06/27 – 07/04
HK$2133/nightTotal: HK$14931 (7 )
70 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Longboat Key
This one-bedroom apartment is located directly on the beach in Longboat Key, offering partial views of Sarasota Bay and within 500 meters of shops and restaurants, including Publix and CVS. This family-friendly flat, covering 70 square meters and accommodating up to four guests, features air conditioning, a swimming pool, a balcony, and a kitchen with a fridge, freezer, microwave oven, and dishwasher, with a 20% discount currently available on many dates.
