Longboat Key, FL Short term rentals

1757 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Longboat Key, FL short term rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Longboat Key, FL

Best Longboat Key, FL short term rentals with a balcony

Paradise On The Sarasota Bay, Close To Gulf Beaches, Heated Pool, Restaurant - Longboat Key, FL
8.8 35 reviews

Paradise On The Sarasota Bay, Close To Gulf Beaches, Heated Pool, Restaurant

apartment, Whitfield
This studio apartment is located in Whitfield Estates, Sarasota, just 15 kilometres from the white sand beaches of Siesta Key, Lido Key, Longboat Key, and Anna Maria Island. The apartment has a very good user rating and is situated within a Ramada hotel, offering access to a range of amenities and activities.
The apartment is 33 square metres in size and can accommodate up to three guests. It features a fully equipped kitchenette, a king bed, a double reclining loveseat, and a 43-inch HD Streaming Smart TV, as well as access to a waterfront tiki bar, restaurant, heated pool, and marina with boat rentals.
Gulf-view Beachfront Condo Unit 203 Longboat Key - Longboat Key, FL
No reviews

Gulf-view Beachfront Condo Unit 203 Longboat Key

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.
Fm Shorewalk,  Near Anna Maria Island Beaches And Img, Pools, Tennis, Pickleball - Longboat Key, FL
9.5 36 reviews

Fm Shorewalk, Near Anna Maria Island Beaches And Img, Pools, Tennis, Pickleball

apartment, Bradenton
This two-bedroom apartment is located in Bradenton, just over 1.5 kilometres from both Arcadeland and IMG Academy, making it ideal for families and sports enthusiasts. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is 116 square metres in size and can comfortably accommodate up to four guests. It features a fully equipped kitchen, two bathrooms, a washing machine, a patio, a TV, parking, internet access, and table tennis, ensuring a comfortable and enjoyable stay.
Sf Shorewalk, Near Anna Maria Island Beaches And Img, Pools, Tennis, Pickleball - Longboat Key, FL
9.8 78 reviews

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

apartment, Bradenton
This two-bedroom apartment is located just 5km from IMG Academy, Smugglers Cove Adventure Golf, and IMG Soccer Academy, making it an ideal choice for families visiting athletes or those interested in sports-related activities. It has received excellent ratings for location, cleanliness, and overall user experience.
The 116 square metre apartment can comfortably accommodate up to four guests. Enjoy the Florida sunshine with the outdoor pool, spa tub, barbecue grills, and tennis court, or relax with free Wi-Fi in the apartment or public areas.

Compare Family-Friendly Holiday Lets in Longboat Key, FL

A short-term let built for families near the water in Longboat Key, FL means plenty of room to spread out and a much smoother experience.

Tranquil Luxury Condo Near Anna Maria Island Beach, 2 Heated Pools, Hot Tubs,img - Longboat Key, FL
9.8 73 reviews

Tranquil Luxury Condo Near Anna Maria Island Beach, 2 Heated Pools, Hot Tubs,img

apartment, South Bradenton
This Bradenton apartment is conveniently located within 5 kilometres of IMG Academy, Smugglers Cove Adventure Golf, and the IMG Bollettieri Tennis Academy.
The two-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen, free Wi-Fi, a swimming pool, hot tub, tennis court, and barbecue grills; housekeeping is available on request.
Dog Friendly And Perfect Lbk Location - Longboat Key, FL
10 21 reviews

Dog Friendly And Perfect Lbk Location

apartment, Longboat Key
This Longboat Key holiday flat is situated across from Gulf of Mexico Drive, a 0.96-kilometre walk from the beach and less than 1.6 kilometres from restaurants such as Harry's, Euphemia Haye, and the Lazy Lobster.
The 149-square-metre, three-bedroom property features an open-plan layout, sleeps six guests, and offers direct access to Cedar's Racquet Club with a pool, tennis courts, and bike rentals; a screened porch with a grill and ping pong table is also available.
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.
Cute Home With Pool, Spa, Mini Golf Walk To Beach! - Longboat Key, FL
9.9 100 reviews

Cute Home With Pool, Spa, Mini Golf Walk To Beach!

apartment, Holmes Beach
This beachfront holiday home is situated in Holmes Beach, Florida, within 1.6km of Bradenton Beach and a short walk from Island Gallery West, offering easy access to Manatee Public Beach (within 2.4km).
The single-bedroom, single-bathroom property sleeps four guests and boasts a private pool, jacuzzi, BBQ, fully equipped kitchen, free Wi-Fi, and Smart TV, ideal for families.

Frequently asked questions about short term rentals in Longboat Key, FL

  • Which top landmarks you shouldn't miss in Longboat Key, FL?

    Well, you definitely want to check out the Longboat Key Beach, it's a classic. Also, the St. Armands Circle is a must-see for shopping and dining. If you're looking for something a bit different, the Mote Marine Laboratory & Aquarium is fascinating.
  • What are the best short term rentals in Longboat Key, FL?

  • What kind of weather can travelers expect in Longboat Key, FL?

    Longboat Key has a subtropical climate, so expect warm temperatures year-round. Summers are hot and humid, with temperatures around 30 degrees Celsius. Winters are mild, with temperatures averaging around 20 degrees Celsius. You'll get plenty of sunshine, but there's always the chance of a sudden downpour.
  • What are the best short term 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 short term rentals with a pool in Longboat Key, FL.

  • Are there any famous stadiums or sports arenas in Longboat Key, FL?

    Longboat Key doesn't have any major stadiums or sports arenas. It's more of a laid-back, beachy destination. But if you're looking for some sporting action, you can head over to Sarasota, about a 15-minute drive away, where you can find the Ed Smith Stadium, home to spring training for the Baltimore Orioles.
  • What are the best short term rentals with a jacuzzi in Longboat Key, FL?

  • What notable natural landmarks are near Longboat Key, FL?

    Longboat Key is located on a barrier island, so you're surrounded by beautiful beaches and coastal scenery. The nearby Myakka River State Park is a great place to explore the Florida wilderness. And if you're looking for a bit of history, the Marie Selby Botanical Gardens in Sarasota is a beautiful spot with a variety of tropical plants.
  • What are the best short term rentals for families and kids in Longboat Key, FL?

  • What part of Longboat Key, FL is ideal for finding lodging?

    The whole island is pretty great for finding lodging, but the south end tends to be a bit quieter and more relaxed. The north end has more restaurants and shops, so it depends on what you're looking for. Most hotels are located along the Gulf of Mexico, so you'll have easy access to the beach.

Popular destinations

Top-Rated Coastal Short-Term Rentals in Longboat Key, FL

Base your upcoming maritime holiday at comfortable shoreside short-term rentals in Longboat Key, FL near the water.

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.

Best Longboat Key, FL short term rentals with a kitchen

3-bedrm House! 15 Min-anna Maria! 5 Min To Img! - Longboat Key, FL
9.8 24 reviews

3-bedrm House! 15 Min-anna Maria! 5 Min To Img!

apartment, South Bradenton
This three-bedroom house, situated in South Bradenton, Florida, is approximately 24km from Anna Maria Island and Bradenton Beach.
The property boasts a fully equipped kitchen, dishwasher, swimming pool, a game room, and accommodates up to seven guests, with beach essentials provided for easy access to the nearby coast.
Family Nest Bradenton Luxury/ Hot-tub/near Beaches - Longboat Key, FL
10 22 reviews

Family Nest Bradenton Luxury/ Hot-tub/near Beaches

apartment, Bayshore Gardens
This two-bedroom flat in Bayshore Gardens is located in a quiet, family-friendly neighbourhood, 8 kilometres from Sarasota-Bradenton Airport and 800 metres from IMG Academy, offering straightforward access to local beaches and the cities of Sarasota and Tampa.
This apartment, which accommodates up to five guests, features a fully equipped kitchen with a breakfast nook, a spacious living room, a master bedroom with a queen-size bed, a garden with seating and barbecue facilities, and an on-site laundry room.
Playa Esmeralda Suite 4 - Longboat Key, FL
9.0 29 reviews

Playa Esmeralda Suite 4

apartment, Bradenton Beach
Playa Esmeralda Unit C, a self-catering apartment in Bradenton Beach, Florida, is a two-minute walk from Cortez Beach and within a 24km radius of Anna Maria City Pier and the Greens of Manatee Golf Club.
This one-bedroom flat offers 42 square metres of space, sleeping up to seven guests and including free Wi-Fi, private parking, and a kitchen equipped with a fridge and microwave.
Beachfront Villa On Serene Gulf Of Mexico - Longboat Key, FL
9.4 62 reviews

Beachfront Villa On Serene Gulf Of Mexico

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 short term rentals with laundry available

Charming Cabana Beach Club #8 - Your Coastal Retreat Awaits!#9 Also Available. - Longboat Key, FL
9.8 172 reviews

Charming Cabana Beach Club #8 - Your Coastal Retreat Awaits!#9 Also Available.

apartment, Longboat Key
Cozy Beach Studio  Silver Sands #251a By Rva - Longboat Key, FL
8.6 128 reviews

Cozy Beach Studio Silver Sands #251a By Rva

studio, Longboat Key
Lovely Townhouse On Sarasota Bay - Longboat Key, FL
10 1 review

Lovely Townhouse On Sarasota Bay

apartment, Longboat Key
Cozy Beach Home Away From Home - Longboat Key, FL
No reviews

Cozy Beach Home Away From Home

apartment, Longboat Key

Popular Holiday Lets with Free Parking in Longboat Key, FL

Free on-site parking comes with these short-term lets near the water in Longboat Key, FL, letting you focus on the coast.

Island Time: Discounted August & September! - Longboat Key, FL
10 383 reviews

Island Time: Discounted August & September!

apartment, Longboat Key
Gulfside 2br Condosilver Sands #257s - Longboat Key, FL
9.1 171 reviews

Gulfside 2br Condosilver Sands #257s

apartment, Longboat Key
Cozy Beach Condo | Longboat Key - Longboat Key, FL
9.6 15 reviews

Cozy Beach Condo | Longboat Key

apartment, Longboat Key
Paradise Suite - Longboat Key, FL
10 42 reviews

Paradise Suite

apartment, Bayshore Gardens

Top Holiday Lets with a Jacuzzi in Longboat Key, FL

Whether you prefer a jacuzzi or a hot tub, these short-term lets near the water in Longboat Key, FL have one included.

Beautifully Furnished Condo - Longboat Key, FL
9.8 195 reviews

Beautifully Furnished Condo

apartment, Bradenton
Shore Thing Beach House W/pool, Spa & Games - Longboat Key, FL
9.6 12 reviews

Shore Thing Beach House W/pool, Spa & Games

apartment, Bradenton Beach
Mycataleya Comfy Condo Near Beach (Bradenton) - Longboat Key, FL
9.3 31 reviews

Mycataleya Comfy Condo Near Beach (Bradenton)

apartment, Bradenton
Exquisite Modern Home With Pool - 10 Min To Beach - Longboat Key, FL
9.8 133 reviews

Exquisite Modern Home With Pool - 10 Min To Beach

apartment, West Bradenton
©2026 cozycozy.com