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Longboat Key, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Longboat Key, FL

Best Longboat Key, FL vacation rentals with a balcony

Condo ∙ 3 Bedrooms ∙ 6 Guests - Longboat Key, FL
No reviews

Condo ∙ 3 Bedrooms ∙ 6 Guests

apartment, Longboat Key
This 3-bedroom, 2-bath condo within the Beachplace Association resort community on Longboat Key offers direct boardwalk access to 1,450 linear feet of beach and spectacular golf course views.
This family-friendly rental includes a fully equipped kitchen, air conditioning, a swimming pool, fitness center, and a Jacuzzi, with a guest capacity of 6.
Bright 2br Bradenton Beach Bungalow With Parking And Washer And Dryer - Longboat Key, FL
9.3 13 reviews

Bright 2br Bradenton Beach Bungalow With Parking And Washer And Dryer

house, Bradenton
This newly renovated 2-bedroom bungalow in Bradenton is located 8.4 miles from the Sarasota International Convention Center and 8.8 miles from the John and Mable Ringling Museum of Art, offering convenient access to local attractions and Sarasota Bradenton International Airport, which is 6.8 miles away.
This vacation home provides 1000 square feet of living space, accommodates up to 7 guests with 2 bedrooms and 1 bathroom, and features a fully equipped kitchen, in-unit washer/dryer, complimentary Wifi, a patio with outdoor dining, and a picnic area, with long-stay deals available.
Steps To #1 Beach In America Siesta Beach! - Longboat Key, FL
9.6 81 reviews

Steps To #1 Beach In America Siesta Beach!

house, Siesta Key
This 2-bedroom, 2-bathroom vacation home in Siesta Key Village is highly rated for its excellent location, cleanliness, and user experience. It is just a short distance from Siesta Key Beach, Shell Beach, and Crescent Beach, and within easy reach of popular attractions and landmarks.
The house features a fully equipped kitchen, multiple bathrooms, laundry facilities, an outdoor balcony, entertainment amenities, barbecue grills, and a tennis court. It can accommodate up to 4 guests and is pet-friendly.
Bayside Comfort | 2br Condo With Beach Access & Resort Amenities - Longboat Key, FL
9.4 3 reviews

Bayside Comfort | 2br Condo With Beach Access & Resort Amenities

apartment, Longboat Key
This beachfront Longboat Key condo, located on Gulf of Mexico Drive, offers direct beach access and is conveniently close to St. Armands Circle and the University Town Center Mall.
The 950-square-foot unit features three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, a west-facing balcony with sunset views, a heated pool, and free on-site laundry.

Guest-Favorite Family Vacation Rentals in Longboat Key, FL

Find the perfect family vacation rental or Airbnb in Longboat Key, FL with plenty of room to spread out near local beaches.

Sunset And Beach View Apartment 402 - Longboat Key, FL
9.0 3 reviews

Sunset And Beach View Apartment 402

apartment, Longboat Key
This Marathon condo rental boasts sunset and beach views on Russell Key, conveniently located 6.4 miles from the Seven Mile Bridge and 29 miles from Upper Matecumbe Key, near Florida Keys Aquarium Encounters.
The 700-square-foot, one-bedroom unit sleeps up to 11 guests and features a fully equipped kitchen, private parking, a swimming pool, Wi-Fi, and a terrace—perfect for enjoying the Florida Keys climate.
'Ocean Breeze Oasis' W/ Boat Dock & Slip On Canal! - Longboat Key, FL
9.3 124 reviews

'Ocean Breeze Oasis' W/ Boat Dock & Slip On Canal!

house, Bayshore Gardens
This Bayshore Gardens vacation home, located in Bradenton near Sarasota Bradenton International Airport (1.9 miles) and Van Wezel Performing Arts Hall (3.9 miles), offers convenient access to area attractions.
The 1450-square-foot property features three bedrooms, a private boat dock, a swimming pool, a jacuzzi, free bicycles, and a fully equipped kitchen, comfortably accommodating families or groups.
Siesta Key 2-bedroom Condo With Pool - Longboat Key, FL
9.4 57 reviews

Siesta Key 2-bedroom Condo With Pool

house, Siesta Key
This recently renovated Sarasota condo is conveniently located near Crescent Beach, a short 1.2-mile drive from Turtle Beach and 11 miles from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 900-square-foot vacation home features two bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating families or small groups; free Wi-Fi and parking are included.
Duke & Sugars  Family Friendly ️ Retro Florida Vibes ,3 Br ,2 Bath, Pool Home . - Longboat Key, FL
10 54 reviews

Duke & Sugars Family Friendly ️ Retro Florida Vibes ,3 Br ,2 Bath, Pool Home .

apartment, West Bradenton
This family-friendly vacation home is located in Palma Sola, just a short distance from Bradenton, within a mile of De Soto National Memorial and Palma Sola Botanical Park. The home has received excellent reviews and is a popular choice for families and groups.
This 3-bedroom, 2-bathroom house spans 1850 square feet and can comfortably accommodate up to 8 guests. Enjoy amenities like a private pool and spa tub, a game room, a barbecue grill, a garden, and a fully equipped kitchen.

Frequently Asked Questions about vacation rentals in Longboat Key, FL

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

    For a first-timer, you've got to visit St. Armand's Circle. It's a charming area with upscale shops, restaurants, and the famous St. Armand's Circle Park with its iconic clock tower. And of course, don't miss the beautiful white sand beaches of Longboat Key.
  • What are the best Airbnb and vacation rentals in Longboat Key, FL?

    Spectacular Beach & Dolphin Views Huge Private Balcony 2br/2ba Upstairs Villa, Anna Maria Island Beach Palms 2b and The Beach On Longboat Key are the most popular Airbnb and vacation rentals in Longboat Key, FL among travelers.

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

    The north end of Longboat Key is a great option for vacation rentals. You'll find a mix of luxury condos and private homes, and it's close to the beach and some great restaurants.
  • 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 must-see for families. It's a great place to learn about marine life and see some amazing creatures up close. The Longboat Key Club & Resort also has a great kids' club, and the beach is always a hit with families.
  • What are the best vacation rentals with a pool in Longboat Key, FL?

    Anna Maria Island Beach Palms 2b, The Beach On Longboat Key and 4411 Shorewalk 15 Min To Beach And 5 Mins To Img are the best vacation 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 in Longboat Key is during the shoulder seasons, from April to May or September to October. You'll find better deals and fewer crowds during these months.
  • What are the best rentals for families and kids in Longboat Key, FL?

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

    You can't beat a day at the beach in Longboat Key. It's free, and there are plenty of public access points. Take a stroll along the Gulf of Mexico, or pack a picnic and enjoy the beautiful views.
  • 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 seafood, try The Lazy Lobster. They have a great atmosphere and fresh seafood, and they're known for their delicious lobster rolls. The Euphemia Haye is another favorite, with a classic menu and a focus on fresh, local ingredients.
  • What are the best walking or cycling routes in Longboat Key, FL?

    The Longboat Key bike path is a great way to explore the island. It runs along the Gulf of Mexico and offers stunning views of the water. You can also take a walk or bike ride on the Longboat Key Nature Trail, which winds through a mangrove forest.
  • Are there pet-friendly attractions in Longboat Key, FL?

    Many of the beaches in Longboat Key are dog-friendly, especially during the off-season. Check with the individual beach before you go. You'll also find pet-friendly restaurants and shops around town.
  • What are the benefits of choosing a vacation rental in Longboat Key, FL?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like a kitchen and laundry facilities. You can also find rentals in different locations, from beachfront properties to more secluded spots.
  • What are the top sports attractions and facilities in Longboat Key, FL?

    The Longboat Key Club & Resort has a great golf course, tennis courts, and a fitness center. There are also several public tennis courts and pickleball courts in the area.

Popular destinations

Best Longboat Key, FL vacation rentals with parking

Kingston Arms 1st Floor - Longboat Key, FL
9.8 96 reviews

Kingston Arms 1st Floor

house, Sarasota
Kingston Arms 1st Floor Right, a Sarasota vacation rental, is located near St. Armands Circle, a three-minute walk away, and offers easy access to Lido Beach, South Lido Beach, Longboat Key, and the John and Mable Ringling Museum of Art (5.9 miles).
This 1,100-square-foot house features a fully equipped kitchen, a private parking space, an elevator, a swimming pool, a spa, and free Wi-Fi; nearby attractions include Mote Marine Laboratory (1.6 miles).
The Beach Condo #107 Beachfront Full View - Longboat Key, FL
9.8 308 reviews

The Beach Condo #107 Beachfront Full View

apartment, Longboat Key
This beachfront condo is located just steps from Longboat Key Beaches and within a short drive of Lido Beach and St. Armands Circle, offering easy access to the area's best attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 330 square foot apartment comfortably sleeps four guests and includes a fully equipped kitchen, a private bathroom, and a balcony. Amenities include a swimming pool, a hot tub, a barbecue area, and free WiFi in public areas.
Mycataleya Beautiful Florida Condo (Bradenton) - Longboat Key, FL
9.5 54 reviews

Mycataleya Beautiful Florida Condo (Bradenton)

apartment, Bradenton
This 2-bedroom condo is located in a resort-style community just a 2-minute walk from the clubhouse, pools, spas, tennis courts, and BBQ facilities. The property enjoys excellent user, location, and cleanliness ratings.
The unit offers a comfortable layout for up to 4 guests and features a king-size bed in the master bedroom and twin beds in the second bedroom. You'll enjoy access to a range of on-site amenities including a fitness center, swimming pool, Jacuzzi, and garden, as well as convenient features like a full-size washer and dryer, a large-screen smart TV, and free Wi-Fi.
Coastal Comfort - Beach Castle #23 By Rva - Longboat Key, FL
10 65 reviews

Coastal Comfort - Beach Castle #23 By Rva

apartment, Longboat Key
This waterfront condo building is ideally situated within 1 mile of Longboat Key Beaches and Cannons Marina, and 3 miles from Jewfish Key. The resort has excellent ratings for its location, cleanliness, and user experience.
The "Walk To Beach/bay, 1st Floor, Beach Castle #23" offer is a 1-bedroom, 1-bathroom condo that can accommodate up to 4 guests. The condo features a fully equipped kitchen, comfortable living area, laundry facilities, and barbecue grills. Guests also have access to a swimming pool, jacuzzi, tennis court, and parking.

Check Out Vacation Rentals with a Pool in Longboat Key, FL

A vacation rental with a pool in Longboat Key, FL is the perfect amenity to complement your time spent by the water.

Island Getaway - 205 - 56th - Longboat Key, FL
9.7 51 reviews

Island Getaway - 205 - 56th

house, Holmes Beach
Island Getaway - 205 - 56th is a Holmes Beach vacation home, a short walk from Anna Maria Island and less than two miles from Bradenton Beach and the Anna Maria City Pier.
This 1710-square-foot property boasts two bathrooms, a private pool and spa, a fitness center, and a fully equipped kitchen, perfect for families seeking a relaxing getaway near the Greens of Manatee Golf Club and the Ringling Museum of Art.
Sutton Place #102a Condo By Rva - Longboat Key, FL
No reviews

Sutton Place #102a Condo By Rva

apartment, Longboat Key
This Longboat Key condo boasts a direct waterfront location, 0.7 miles from Longboat Key beaches and 2.7 miles from Cannons Marina, offering stunning views and easy access to area attractions.
The two-bedroom, two-bathroom unit sleeps four, features a fully equipped kitchen, in-unit laundry, a private terrace, and access to a swimming pool, fitness center, tennis court, and a game room with barbecue grills.
Vinca | Steps To Siesta Key Village! - Longboat Key, FL
9.5 111 reviews

Vinca | Steps To Siesta Key Village!

house, Siesta Key
This vacation home is located in Siesta Key Village, just a short walk from the famous Siesta Key Beach and other popular beaches, as well as local attractions and restaurants. The property has received excellent ratings for location, cleanliness, and overall experience.
This rental offers a fully equipped kitchen, a comfortable living area with a sofa bed, and a dining area. The home also features a swimming pool, terrace, garden, and parking, perfect for enjoying the beautiful Siesta Key weather.
Silver Sands #237 - Longboat Key, FL
8.0 1 review

Silver Sands #237

house, Longboat Key
This Silver Sands #237 condo in Longboat Key offers direct access to Longboat Key Beach, a 2-minute walk away, and is situated 15 miles from the John and Mable Ringling Museum of Art.
This accommodation features a private balcony, free WiFi, free parking, and a full kitchen, with facilities for disabled guests and a swimming pool, fitness center, and tennis court available.

Find the Best Seaside Vacation Rentals in Longboat Key, FL

Discover beautiful beach towns with these seaside vacation rentals in Longboat Key, FL, perfect for relaxing near the coast and exploring the shore.

Waterfront, Spa, Pool, Private Paradise On Longboat Key - Longboat Key, FL
9.3 3 reviews

Waterfront, Spa, Pool, Private Paradise On Longboat Key

house, Longboat Key
Gulf Front Escape  Silver Sands #252 By Rva - Longboat Key, FL
9.0 108 reviews

Gulf Front Escape Silver Sands #252 By Rva

apartment, Longboat Key
Gulf Tides Of Longboat Key By Coolvacay - Longboat Key, FL
9.3 12 reviews

Gulf Tides Of Longboat Key By Coolvacay

studio, Longboat Key
1/1 Condo, Pool, Beach Access, Washer/dryer - Longboat Key, FL
No reviews

1/1 Condo, Pool, Beach Access, Washer/dryer

apartment, Longboat Key

Discover 5-Star Vacation Rentals in Longboat Key, FL

Experience 5-star comfort in a luxury Longboat Key, FL vacation rental designed with premium amenities throughout.

Beachcomber Unit 203 - Longboat Key, FL
10 4 reviews

Beachcomber Unit 203

apartment, Longboat Key

Best Vacation Rentals with a Steam Room in Longboat Key, FL

Relax with an on-site sauna at these vacation rentals in Longboat Key, FL, perfect for a steam session after a day by the water.

Sauna Cold Plunge Sportscourt Pool Hot Tub - Longboat Key, FL
No reviews

Sauna Cold Plunge Sportscourt Pool Hot Tub

house, Bradenton
Dans Florida Condos Four Palms At Runaway Bay - Longboat Key, FL
10 3 reviews

Dans Florida Condos Four Palms At Runaway Bay

house, Bradenton Beach
Dans Florida Condos Paradise Bay At Runaway Bay - Longboat Key, FL
10 1 review

Dans Florida Condos Paradise Bay At Runaway Bay

house, Bradenton Beach
Runaway Bay 146 - Bay Views, Beach Access, Pool And Gym - Longboat Key, FL
9.7 115 reviews

Runaway Bay 146 - Bay Views, Beach Access, Pool And Gym

apartment, Bradenton Beach
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