Holiday rentals with a pool in Longboat Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Longboat Key

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Seminole

4.87 out of 5 average rating, 259 reviews

⭐️Ultimate Vacation Home🌴Tropical Heated Pool Oasis

🌴 4min to the beach! Over 200 great reviews from guests! 🕶 Huge and gorgeous 4 bedroom home. Living, Dining, AND family room with pool table! Fully equipped kitchen. 🦋⛱PRIVATE tropical outdoor area with sparkling large private HEATED pool, lounging areas, outdoor grill, FIRE PIT! ⛹️‍♂️Basketball on the driveway! If your looking for vacation home here it is! 🏖Minutes away beaches! Beach chairs and beach towels provided. Experience the charm of Florida in a home you will want to call your own

Guest favourite

Home in Clearwater

4.87 out of 5 average rating, 165 reviews

Poolside Bliss in Clearwater! Heated-pool/Spa

HEATED POOL FREE OF CHARGE Your new vacation spot grants you exclusive use of a fully updated 3 bedroom and 2 bathroom home with a private pool! With 3 bedrooms, 7 beds, that sleeps 12 comfortably can accommodate up to 14. This home has an amazing spacious backyard for family gatherings and overall enjoyment of the outdoor spaces.Located 8 miles from the world famous Clearwater beach, it is in a prime location with many events happening nearby.Safely situated in a quiet desirable neighborhood.

Guest favourite

Home in St. Petersburg

4.91 out of 5 average rating, 133 reviews

Heated Pool and hot tub luxury vacation house

Spend your vacation in luxury! The hot tub and heated swimming pool are perfect for a family vacation or a couples' retreat. In winter we keep the pool temperature at 85 degrees. Enjoy the stylish furniture, a huge luxurious master suite with a large walk-in closet and work desk, a fully equipped kitchen and all the extras you would expect at the resorts. The living room features a 75’ TV! Short drive to Madeira Beach and Treasure Island. Small parties are allowed. A lot of parking space.

Guest favourite

Apartment in Clearwater Beach

4.76 out of 5 average rating, 128 reviews

☀Pool✔ Beach✔ Self Checkin✔ Free Parking✔

No hidden fees! No complicated checkout instructions! We make it easy for our guests. ☞ 2 min walk to the beach ☞ Free parking ☞ Heated pool ☞ AC ☞ Self check-in We provide essentials (linen, towels, toilet paper, shampoo, soap, etc.) at the beginning of your stay. We recommend getting more supplies for more extended stays. 648 Poinsettia Ave Clearwater Beach 33767 Location, location, location! 500 feet to the beach 500 feet to a park and playground 0.2 mile to public tennis courts

Guest favourite

Home in Venice

4.92 out of 5 average rating, 118 reviews

Great shape after Milton -Gorgeous Pool! - os

Great news! We've quickly reopened after Milton! Restaurants, stores, our beach access & Historic downtown-all now open! Beautifully decorated 3 bedrooms, 2 bathrooms, attractive family room & open concept kitchen with breakfast room overlooking private pool. On desirable Island of Venice, “Villa Sorrento” is only 8 minute walk to beach. Near Historic Venice Avenue's unique shops, restaurants. Low-key quiet vacationers only. 2 car max. no visitor parking. No pets. No smoking

Superhost

Home in Bradenton

5 out of 5 average rating, 4 reviews

Lakefront Pool Home w/Resort Amenities Near Beach

Escape to this lakeside haven with a private pool, just minutes from the pristine beaches of Siesta Key, Anna Maria Island, Bradenton Beach & Lido Key. Relax in the serene setting or explore the nearby sandy shores. Whether you're looking for a peaceful retreat or coastal adventure, this stunning getaway has it all for an unforgettable stay! Perfect for families, friends, or couples seeking both tranquility and excitement. Book your slice of paradise today!

Guest favourite

Home in Indian Rocks Beach

4.95 out of 5 average rating, 63 reviews

Stunning Waterfront Pool Home Walk to Beach

Relax at the Twin Dolphins luxury pool home, your five star vacation paradise! Bright and open freshly remodeled and ready for your visit. Large heated private pool offers fun for everyone. Well equipped and actively managed, so you are well cared for. This property offers the best of pool and beach living at a fraction of resort prices. You rent the entire property, 4 bedrooms, 3 baths, a large rec room, private heated pool, and private dock.

Superhost

Home in Oldsmar

4.84 out of 5 average rating, 19 reviews

Exquisite Fun Getaway with Private Pool!

Step into our charming Airbnb nestled in the heart of Oldsmar, Florida, where the perfect blend of opulence and practicality awaits you in a cozy, one-story retreat. Immerse yourself in the allure of this enchanting escape, designed to provide an unparalleled experience for guests in search of tranquility, outdoor pursuits, and a sprinkle of historical allure.

Guest favourite

Home in Bradenton

4.88 out of 5 average rating, 123 reviews

Coastal Charm

Charming 3 bedroom, 2 bath home with room to explore. Beautiful swimming pool that overlooks pond and x-large patio to enjoy outdoor dining and relaxing. Coastal decor throughout to enjoy your tropical surroundings. Just 5 miles and easy passage to the beach this home makes for an affordable beach vacation.

Superhost

Home in Sarasota

4.84 out of 5 average rating, 57 reviews

SieSta Key is Open,Heated Pool, 5min to Siesta key

Less than 2 miles to SIESTA BEACH public access #12 NO PARTIES OR EVENTS ALLOWED This is a happy place! You will find peace and tranquility in the spacious friendly home. Close to shops, bars, restaurants and less than 5min drive from Siesta Key Beach, voted #1 BEST BEACH IN USA in 2017