
House holiday rentals in Longboat Key
Find and book unique houses on Airbnb
Top-rated house rentals in Longboat Key
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Longboat Key
House rentals with a pool

Retreat by the Bay-Heated Saltwater Pool
Will's place was amazing! Super clean, comfortable, and exactly as described. The location was perfect - there was so much to do nearby, from the beach, great restaurants and shops. Will was also a fantastic host: responsive and helpful. Highly recommend staying here if you're looking for a spot that's both relaxing and close to all the action!

Pool, Spa, & Private Gym in the Heart of Sarasota
We had a great stay at the house. Loved the interior decor. Looks like the home was remodeled recently. Everything was fresh and clean. We loved hanging out by the pool. Backyard was very private and peaceful. Posts were very quick with their responses if I had any questions about the home. We would definitely stay at the Home again when we’re in town.

Island in the Sun, luxury beach house,private pool
Had the absolute best stay here! Everything was perfect, from the interior design to the location. The pool was great with lots of privacy in the backyard. The house was spacious, each bedroom having a king and its own bathroom. My son loved that. We would love to stay here again!

Wk of 6/29 now avail at last minute SALE rate!
We had an absolutely fantastic time. The home was delightful. The ease of getting to and from the beach plus all the beach chairs and amenities Mark provided for the beach really made it all so easy. Our kids loved the pool and the set up. Beds were very comfortable. Everything was easy to find. Thank you so much for letting us enjoy your home!!!

Waterfall | Spa | Saltwater Pool | Private Oasis B
The house is located in a great location! The beach is not a far drive and there is plenty to do in the area! The house is also beautiful and the backyard with the pool and hot tub are amazing !

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!
Just checked out of Kate’s place! What can we say, as a family of five and also our parents we had the most amazing stay. The property is as described, super clean and spacious! The kids loved the pool area and spend countless hours playing around the pool and with the vast array of games throughout the villa. The Area was beautiful, gorgeous beaches and friendly people! Kate was an amazing host, always insightful, friendly and very responsive. What a fabulous family holiday full of lots of new memories created. Thanks Kate!

Pickleball | Heated Pool | Game Room | 4 Min to Be
10 toes down best Air B&B I’ve stayed at. My best friend’s wife is built like a Baluga whale and even she fit in the bed.

Walk to Lido Beach &St. Armands -grill/HEATED POOL
Book this immediately! This house is a beautiful, peaceful, tropical oasis that is close to the beach and restaurants. After a day at the beach, the private pool is a great escape. Claudia was very responsive and kind, she answered any questions we had. We were provided with a great starter pack of house items so we could start relaxing right away!
Weekly house rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
This Airbnb exceeded every expectation! The property was beautiful, spotless, and incredibly well-maintained. The pool was a highlight—clean, peaceful, and the perfect spot to relax every day. The host was friendly, responsive, and made sure we had everything we needed for a comfortable stay.

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.

Coastal Retreat near Siesta Key Beach and Downtown
We had the most perfect stay at Aubrey’s! We loved everything about it! Great location, so comfortable and nice, close to great restaurants and close to beach as well. The design features of the house and everything in it is very well curated and a house you want to spend time in and enjoy the beauty. The beach chairs and umbrella were perfect for the beach. We highly recommend Aubrey’s place and will definitely stay here when we come back! Melissa and John

Loggerhead - AMI Oasis w/ Private Pool + Golf Cart
Ross and Hannah’s place was great for our family if 5! The pool with tv set up was amazing for our kiddos many movies in the pool during the week made it so much fun! We also loved the convenience of using the golf cart, was so close to shops and restaurants (we only used our rental car once to go to Cortez)! Hannah was also very quick to respond and s gracious host. We would recommend to families coming to ami- a good value!!

Cozy Cottage - close to Manatee River
Cute Airbnb ! Very well decorated and super cozy. Easy drive to Anna Maria Island

Lovely House in Sarasota Bay
Host was very friendly and responsive. House was great, as described and very clean!

* Anna Maria Sunrise Escape A *
Thanks for all the help. I appreciate the quick response to anything that came up and looking forward to the next time.

Home w Pool on Venice Island
Beautiful home, just like the pictures! Exceptionally clean. Yuliya was a great host! Very informative and friendly, making sure we had everything we needed!! This location was perfect for relaxing by the pool in the quiet neighborhood as well as taking the short drive to beach for shark tooth hunting!! We look forward to staying again the future!
Private house rentals

100 yr Old Stone Home by Beaches

Great House / Great Location ~ with Heat Pool~

Chasing the Sun Lido Beach House

Downtown Oasis: Poolside Condo, Patio & Gym

Rollin' wth the Waves by Beach Boutique Rentals

Sea La Vie by Duncan Real Estate

Coastal Elegance Pool Home in Sarasota

Manatee Sanctuary - heated pool and spa (hot tub)
Quick stats about house rentals in Longboat Key
Total rentals
220 properties
Nightly prices starting at
₹2,596 before taxes and fees
Total number of reviews
3.9K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
140 properties have a pool
Destinations to explore
- St Petersburg Holiday rentals
- Tampa Bay Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Townhouse rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with an EV charger Longboat Key
- Rentals with lake access Longboat Key
- Waterfront rentals Longboat Key
- Beachfront rentals Longboat Key
- Fitness-friendly rentals Longboat Key
- Beach apartment rentals Longboat Key
- Flat rentals Longboat Key
- Rentals with beach access Longboat Key
- Cottage rentals Longboat Key
- Rentals with a firepit Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with a patio Longboat Key
- Apartment rentals Longboat Key
- Pet-friendly rentals Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Rentals with pools Longboat Key
- Rentals with a hot tub Longboat Key
- Beach house rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- House rentals Manatee County
- House rentals Florida
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park