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Best Vacation rentals and Airbnb offers in Longboat Key, FL
9.5 309 reviews
Longboat Key, FL
07/11 – 07/17
$273/nighttotal: $1638 (6 )
Beach Front One Bedroom Condo Paradise. Ground Floor.
1 3
apartment , Longboat Key
This studio is located on Longboat Key, just a 2-minute walk from the beach and 12 miles from the John and Mable Ringling Museum of Art. It has received excellent ratings for user experience, location, and cleanliness. The studio is on the ground floor, offering easy access and a private balcony with beautiful views. You can enjoy amenities like a swimming pool, Jacuzzi, tennis court, and a picnic area, all while having access to a fully equipped kitchen and free parking.
9.6 82 reviews
Longboat Key, FL
07/11 – 07/17
$419/nighttotal: $2514 (6 )
Wonderful Canal Front Condo On Lbk! Bring Your Boat!cabana Beach Club Unit 11.
1 3
apartment , Longboat Key
This Longboat Key apartment is located in the peaceful Cabana Beach Club, just a short walk across the street from the Gulf of Mexico beaches. The apartment has an excellent user rating and is perfect for families or groups of up to four people. The 750-square-foot unit has one bedroom and one bathroom. The apartment offers amenities like a private dock, a heated swimming pool, a terrace, and a fully equipped kitchen.
8.7 14 reviews
Longboat Key, FL
10/10 – 10/17
$262/nighttotal: $1834 (7 )
Harbor Villa Club 309
2 4
apartment , Longboat Key
This Longboat Key apartment is located just a short 3-minute walk from the beach, offering easy access to the sand and surf, and within a 15-mile radius of both The John and Mable Ringling Museum of Art and Sarasota Jungle Gardens. It has received excellent user ratings, so you can be sure of a pleasant stay. This two-bedroom, two-bathroom rental includes a fully equipped kitchen, a terrace, and a garden, perfect for enjoying meals and relaxing outdoors. Amenities include a swimming pool, a Jacuzzi, a tennis court, and a restaurant, ensuring you have plenty to do on-site.
10 3 reviews
Longboat Key, FL
07/01 – 07/05
$538/nighttotal: $2152 (4 )
Sleeps 10 - Pool W/ Slide - Games - 6 Min To Img
3 8
apartment , South Bradenton
This 3-bedroom condo in Cedar Run Resort in South Bradenton is located 6 miles from IMG Academy and 10-15 miles from Downtown Bradenton, Anna Maria Island, and Sarasota. This family and dog-friendly vacation rental accommodates up to 10 guests with resort-style amenities including a heated pool with a water slide, putting green, cornhole, Giant Connect 4, and paddleball, along with a fully stocked chef's kitchen, high-speed WiFi, and an in-unit washer and dryer.
10 21 reviews
Longboat Key, FL
10/10 – 10/17
$300/nighttotal: $2100 (7 )
Cozy Private Beach Condo
1 4
apartment , Longboat Key
This Longboat Key condo, located 600 feet from the complex's beachfront amenities and steps from Longboat Key's private beach, offers exceptional Gulf of Mexico views. This two-bedroom, two-bathroom rental sleeps six, features a fully equipped kitchen, a small office space, access to a heated pool and BBQ area, and requires a minimum two-week stay.
9.4 47 reviews
Longboat Key, FL
07/01 – 07/05
$290/nighttotal: $1160 (4 )
Cortez Gardens Cottage 15, Renovated And Close To Beach, 3-bed, 2-bath 10 People
3 8
apartment , Bradenton
This Bradenton apartment is conveniently located just 3.7 miles from Desoto Square Mall and 19 miles from Rosa Fiorelli Winery, offering easy access to shopping, dining, and local attractions. Guests have consistently rated this property excellent for its cleanliness, location, and overall experience. This spacious rental offers 990 square feet of living space, comfortably accommodating up to 10 guests with three bedrooms and two bathrooms. Enjoy modern amenities like free Wi-Fi, air conditioning, and a fully equipped kitchen, along with a private garden, parking, and pet-friendly accommodations.
9.0 1 review
Longboat Key, FL
08/20 – 08/21
$515/nightfor 1 night
Silver Sands #254
1 2
house , Longboat Key
Silver Sands #254 is a beachfront condo in Longboat Key, offering direct access to Longboat Key Beach and located 15 miles from Sarasota International Airport and the John and Mable Ringling Museum of Art. This accommodation features a private balcony, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, and parking, with facilities accessible for disabled guests and proximity to cycling activities.
9.2 80 reviews
Longboat Key, FL
11/01 – 04/01
$365/nighttotal: $55115 (151 )
Relax At Gulf Silver Sands Resort #232, Longboat
1 2
apartment , Longboat Key
Silver Sands #232 Resort By Rva is a beachfront condo located in Longboat Key, within a 10-minute walk of Longboat Key Beaches and Cannons Marina. This highly-rated resort offers a one-bedroom, one-bathroom layout with a sofa bed, accommodating up to four guests. The resort features a fully equipped kitchen, TV with DVD player, in-unit laundry facilities, and a garden with barbecue grills. Guests can enjoy amenities such as a swimming pool, tennis court, parking, and complimentary Wi-Fi.
9.0 79 reviews
Longboat Key, FL
07/15 – 07/24
$206/nighttotal: $1854 (9 )
Cortez Gardens Cottage 11, Renovated, Close To Beach, 3-bed, 2 Bath 10 People
3 6
apartment , Bradenton
This 3-bedroom apartment is located in Bradenton, just 9 miles from the John and Mable Ringling Museum of Art and a short drive from the beach. The apartment has received excellent ratings for location, cleanliness, and overall experience. The apartment comfortably accommodates up to 10 guests and includes a fully equipped kitchen with a dishwasher and oven. Enjoy the peace and quiet of the street, relax in the garden, and stay connected with free Wi-Fi and private parking.
9.8 19 reviews
Longboat Key, FL
07/01 – 07/05
$318/nighttotal: $1272 (4 )
Palm Tree Home - Private Pool Haven, Pet-friendly!
3 8
apartment , Bradenton
This Bradenton vacation home boasts a central location, less than a mile from Riverwalk, The Bishop Museum of Science and Nature, and the Manatee Performing Arts Center, and within two miles of LECOM Park and Manatee Memorial Hospital. This 1,510-square-foot house comfortably sleeps nine guests and features three bedrooms, two bathrooms, a private pool, a fully equipped kitchen, in-unit laundry, and an outdoor patio with barbecue grills.
Longboat Key, FL
08/20 – 08/21
$270/nightfor 1 night
Zota Beach Resort
1 2
resort , Longboat Key
Zota Beach Resort offers pet-friendly accommodations in Longboat Key, Florida, conveniently located within walking distance of the city center. The resort features a swimming pool, on-site restaurant and bar, fitness center, business center, and offers room service, along with concierge services and car rentals.
9.7 81 reviews
Longboat Key, FL
07/01 – 07/05
$481/nighttotal: $1924 (4 )
Sea Salt Retreat Pool Home 5 Miles From The Beach Home
3 8
house , West Bradenton
This vacation home is located in Bradenton, just a short drive from the beautiful beaches of West Bradenton and close to Palma Sola Causeway Park. The house consistently receives excellent ratings for its cleanliness, location, and overall user experience. This 1880 square foot rental features a fully equipped kitchen, a private pool, and a relaxing outdoor patio. You can enjoy air conditioning, laundry facilities, and free private parking, as well as nearby cycling opportunities.
Best Longboat Key, FL vacation rentals with a balcony
9.0 1 review
Longboat Key, FL
08/20 – 08/22
$401/nighttotal: $802 (2 )
Beach Castle Resort #12
1 2
house , Longboat Key
Beach Castle Resort #12 is a house located in Longboat Key, just a 4-minute walk from Longboat Key Beach and 14 miles from the John and Mable Ringling Museum of Art. This 910 sq ft accommodation features 2 bedrooms and 2 bathrooms, accommodates up to 11 guests, and includes a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a patio, a balcony, and complimentary WiFi and parking.
9.6 9 reviews
Longboat Key, FL
06/27 – 07/04
$293/nighttotal: $2051 (7 )
Stunning Canal Condo - Walk To Beach - Sleeps 4
2 2
apartment , Longboat Key
This Longboat Key waterfront condo is less than a mile from Longboat Key Beaches and Cannons Marina, offering easy access to boating and water activities, with Jewfish Key approximately 2.9 miles away. The two-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, a private balcony, free Wi-Fi, and access to a spa and parking.
9.4 26 reviews
Longboat Key, FL
11/01 – 04/01
$363/nighttotal: $54813 (151 )
Blue Oasis 5512, Your Private Getaway
3 2
apartment , Bayshore Gardens
This 3-bedroom, 2-bathroom apartment in Bayshore Gardens, Bradenton, offers a prime location adjacent to a golf course and near the beach, with St. Armands Circle just a 17-minute drive and Lido Beach a 27-minute drive away. This spacious 1170 sq ft vacation rental accommodates up to 8 guests and features a private swimming pool, lanai, fire pit, in-unit laundry, and a fully equipped kitchen with an oven, stovetop, refrigerator, coffee maker, electric kettle, and microwave, plus air conditioning and Wi-Fi.
10 3 reviews
Longboat Key, FL
07/15 – 07/24
$233/nighttotal: $2097 (9 )
Ami, 2 Heated Pools, Img, 2 Hot Tubs, Pickleball.
2 6
apartment , Bradenton
This 2-bedroom, 2-bathroom condo in Bradenton offers a prime location, just 1 mile from IMG Academy and 8.3 miles from Anna Maria Island, with convenient access to local amenities. This 1170 sq ft apartment accommodates up to 6 guests and features a screened-in balcony with pond views, access to heated pools, jacuzzis, tennis, basketball, and on-site BBQ grills, along with provided beach essentials.
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.
10 356 reviews
Longboat Key, FL
06/27 – 07/04
$406/nighttotal: $2842 (7 )
Are You Ready For A Luxury 5-floor Penthouse 60 Ft From Water, 207 Reviews
1 2
apartment , Longboat Key
This Longboat Key beach apartment is just a short walk from the beach and a short drive from Cannons Marina, offering a peaceful escape in a convenient location. The property has received excellent ratings for user experience, location, and cleanliness, making it a highly recommended choice for travelers. This one-bedroom apartment comfortably accommodates up to six guests in 800 square feet of space. Enjoy the beautiful beach, relax in the swimming pool or jacuzzi, and take advantage of amenities like a fully equipped kitchen, a fireplace, and a private terrace or balcony.
9.8 59 reviews
Longboat Key, FL
07/11 – 07/17
$203/nighttotal: $1218 (6 )
Top Floor Corner Unit 2 Bedroom Condo In Shorewalk Anna Marie Island 15 Min
2 3
apartment , Bradenton
This Bradenton golf condo rental is conveniently located within three miles of IMG Academy, IMG Golf Academy, and Smugglers Cove Adventure Golf, offering easy access to area attractions. This 1,090-square-foot unit features two bedrooms, two bathrooms, and accommodates four guests, boasting a fully equipped kitchen, free Wi-Fi, a swimming pool, and a tennis court.
9.7 152 reviews
Longboat Key, FL
07/20 – 07/22
$288/nighttotal: $576 (2 )
Tides Inn On The Bay Vacation Homes
1 1
house , Bradenton Beach
Tides Inn on the Bay Vacation Homes is ideally located steps away from Cortez Beach and a short walk from Bradenton Beach. It boasts excellent user, location, and cleanliness ratings. The house features one bathroom, a fully equipped kitchen, air conditioning, and a terrace or balcony. Guests can also enjoy a barbecue on the sun terrace, or go fishing nearby. Free Wi-Fi and private parking are also available.
10 143 reviews
Longboat Key, FL
06/27 – 07/04
$136/nighttotal: $952 (7 )
Quiet Nights Of Quiet Stars On Anna Maria Island
2 2
cottage , Holmes Beach
This beach house is located in Holmes Beach, a short walk from Bradenton Beach and Island Gallery West, and less than a mile from Holmes Beach Beaches and Manatee Public Beach. It has received excellent user ratings, making it a popular choice for travelers. This two-bedroom vacation rental comfortably accommodates up to four guests. The property offers amenities like a playground, barbecue grills, a private terrace, and a fully equipped kitchen. Enjoy easy access to the beach, nearby attractions, and activities like swimming, sunbathing, and fishing.
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?
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?
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.
Destinations nearby
Best Longboat Key, FL vacation rentals with parking
9.2 28 reviews
Longboat Key, FL
07/11 – 07/17
$175/nighttotal: $1050 (6 )
Mycataleya Comfy Condo Near Beach (Bradenton)
2 3
apartment , Bradenton
This Bradenton rental is conveniently located near the river, 6.2 miles from Sarasota Bradenton International Airport and 8.5 miles from the Ringling Museum of Art. This 1080-square-foot, two-bedroom, two-bathroom condo sleeps seven and boasts a private balcony with river views, a fully equipped kitchen, and access to a pool, hot tub, tennis court, and more.
This Longboat Key apartment is just a 15-minute walk from Cannons Marina and Longboat Key Beaches, with Jewfish Key and Coquina Beach also within a 3-mile radius. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. This two-bedroom, two-bathroom condo has 1550 square feet of space and can comfortably accommodate up to four guests. Enjoy a relaxing stay with amenities like a swimming pool, jacuzzi, terrace, garden, and free WiFi, along with a fully equipped kitchen, and direct access to the waterfront.
Longboat Key, FL
07/01 – 07/05
$380/nighttotal: $1520 (4 )
Sleeps 8 - Pool W/ Slide - Games - 6 Min To Img
4 8
apartment , South Bradenton
This 2-bedroom condo in Cedar Run Resort, South Bradenton, is located 6 miles from IMG Academy and 10-15 miles from Downtown Bradenton, Anna Maria Island, and Sarasota. This 1250 sq ft unit accommodates up to 8 guests and features resort-style amenities including a heated pool with a water slide, putt-putt, corn hole, Giant Connect 4, a chef's kitchen, workspace with high-speed WIFI, and provided beach essentials.
9.6 70 reviews
Longboat Key, FL
07/15 – 07/24
$206/nighttotal: $1854 (9 )
Tranquil Luxury Condo Near Anna Maria Island Beach, 2 Heated Pools, Hot Tubs,img
2 6
apartment , Bradenton
This Bradenton condo rental is conveniently located within three miles of IMG Academy, Smugglers Cove Adventure Golf, and the IMG Bollettieri Tennis Academy. This two-bedroom, two-bathroom unit sleeps six, boasting a fully equipped kitchen, free Wi-Fi, a private terrace, and access to a swimming pool, jacuzzi, and tennis court; housekeeping is available upon request.
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.
9.8 66 reviews
Longboat Key, FL
11/01 – 04/01
$355/nighttotal: $53605 (151 )
Heated Saltwater Pool | 5br | Near Img + Ami
5 2
apartment , Bradenton
This Bradenton vacation home is conveniently located just a short drive from Blake Medical Center and De Soto National Memorial, with easy access to IMG Academy and Palma Sola Botanical Park, making it perfect for exploring the area. This property has received excellent ratings for its cleanliness, location, and overall user experience. The 5-bedroom home offers ample space for families or groups, boasting a spacious 2010 square feet of living area. Enjoy a private pool, outdoor space with a garden and barbecue grills, a fully equipped kitchen, free WiFi, and a DVD player for entertainment.
9.8 42 reviews
Longboat Key, FL
07/01 – 07/08
$384/nighttotal: $2688 (7 )
Beachcomber Unit 303
1 2
apartment , Longboat Key
This Longboat Key beachfront condo is located 0.2 miles from Longboat Key Beaches, within 6 miles of Lido Beach and St. Armands Circle. The two-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen, in-unit laundry, cable TV, a terrace, and access to a swimming pool, tennis court, and direct beach access with provided umbrellas and loungers.
10 10 reviews
Longboat Key, FL
10/10 – 10/17
$353/nighttotal: $2471 (7 )
Updated In Beach Castle, Private Beach Access
1 4
apartment , Longboat Key
This two-bedroom, two-bathroom condo at Beach Castle Resort on Longboat Key offers a prime location, a short two-minute walk from private beach access with chairs, umbrellas, a gas grill, and an outdoor shower, and is also close to St. Armand's Circle and Anna Maria Island. The 2-bedroom unit, sleeping up to eight guests, boasts a fully equipped kitchen, screened-in lanai, resort amenities including a heated pool, hot tub, and tennis/pickleball court, plus dedicated parking.
9.6 51 reviews
Longboat Key, FL
07/11 – 07/17
$203/nighttotal: $1218 (6 )
Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches
2 3
apartment , Bradenton
This Bradenton rental is conveniently located just a mile from Arcadeland and a mile and a half from IMG Academy, making it an ideal spot for families and groups visiting the area. The apartment has received excellent ratings from previous guests, highlighting its comfortable accommodations and convenient amenities. The 2-bedroom, 2-bathroom apartment offers 1170 square feet of space, accommodating up to 6 guests. The rental features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a spa, providing plenty of opportunities for relaxation and recreation.
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.
10 10 reviews
Longboat Key, FL
07/15 – 07/24
$579/nighttotal: $5211 (9 )
Cute Canal Front Cottage With Dock & Boat Lift And Pool ,Short Walk To The Beach
3 6
apartment , Longboat Key
9.6 8 reviews
Longboat Key, FL
06/27 – 07/04
$385/nighttotal: $2695 (7 )
Beachcomber Unit 203
1 2
apartment , Longboat Key
9.6 46 reviews
Longboat Key, FL
10/10 – 10/17
$321/nighttotal: $2247 (7 )
Beach Castle Bliss #22 By Rva
2 4
apartment , Longboat Key
8.7 70 reviews
Longboat Key, FL
06/27 – 07/04
$277/nighttotal: $1939 (7 )
Coquina Moorings 202 · Sunrise & Sunset Views
2 2
apartment , Bradenton Beach
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.
9.8 31 reviews
Longboat Key, FL
10/10 – 10/17
$257/nighttotal: $1799 (7 )
Beautiful Beach Longboat Key Townhouse
2 4
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.
Longboat Key, FL
07/15 – 07/24
$440/nighttotal: $3960 (9 )
Sunsational Lounge Area-steamy Hot Tub
1 6
house , Bradenton
9.8 136 reviews
Longboat Key, FL
08/20 – 08/21
$920/nightfor 1 night
The St. Regis Longboat Key Resort
1 2
resort , Longboat Key
10 2 reviews
Longboat Key, FL
07/20 – 07/22
$2035/nighttotal: $4070 (2 )
New! Lux Estate, Pool, Hot Tub, Sauna, Cold Plunge
8 1
apartment , Bayshore Gardens
10 1 review
Longboat Key, FL
07/15 – 07/24
$1482/nighttotal: $13338 (9 )
Exclusive 5-level Waterfront Solstice House On Sarasota Bay
