Holiday rentals with a pool in Osprey

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Osprey

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

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Guest favourite

Home in Venice

4.9 out of 5 average rating, 51 reviews

Heated POOL close to beach fenced in, kid friendly

Family friendly, Pool home has an open floor plan. New kitchen w/ stainless appliances & a breakfast bar. Living room has sleeper sofa w/ upgraded memory foam mattress. Large sunroom overlooks the fully screened in private pool & fenced tropical backyard. Many amenities: washer & dryer, pool floats, beach chairs, umbrella, beach towels & toys, coolers. 7 min by car to Manasota beach, 5 min to shopping restaurants etc. Primary has ensuite bathroom, walk in closet. Pack n play crib, toys & games!

Guest favourite

Home in West Bradenton

4.99 out of 5 average rating, 140 reviews

Suncoast Beach Getaway - 10 Minutes to Gulf & IMG

Enjoy some of Florida's finest white sandy beaches. Only 4 miles/10 minutes to the shimmering Gulf of Mexico or IMG Academy. This Luxurious 3 bedroom 2 bath pool home has an additional queen futon & queen sleeper sofa. 100% remodeled by builder/owner. Over 2300 square ft. of A/C space (3 zones) all on one level with a huge private HEATED POOL. Featuring a fully stocked gourmet chef kitchen & stunning granite counters! The very large rear lanai could easily serve as a 4th bedroom. Come & relax!

Superhost

Home in North Port

4.81 out of 5 average rating, 133 reviews

Luxury villa 4 bdr with a heated pool (14guests)

Rare to find a luxury villa with a swimmable heated pool at the upscale district of North Port near a golf course. Very spacious (14 guests), high ceiling. Two empty lots on both sides of the property and a canal on the back guarantee full privacy. 2 minutes to Walmart and Publix. 10 minutes to Warm Mineral Spring. Close to Water park, Wellen park, Manasota, Siesta and others beaches. Very close to highways. The home is 2230 sq. ft. of living space. Fully furnished with high-end furniture.

Superhost

Home in North Port

4.84 out of 5 average rating, 31 reviews

Cozy getaway home with Heated Pool!

Fall in love with this cozy vacation Home! Just minutes walk away from Florida's only warm mineral Springs. This freshly renovated home has 3 bedrooms, 2 bathrooms, open layout kitchen dining and living room. The pool is heated and enclosed in the lanai so you don't have to worry about any bugs. There are numerous beaches within 15-30 minute drive. There are multiple golf courses around, aqua park, beautiful parks and many more to enjoy. Many stores, restaurants are located just minutes away.

Guest favourite

Home in Englewood

5 out of 5 average rating, 6 reviews

Pet Friendly Pool Home with Large Private Yard

Charming home nestled in a peaceful neighborhood. The entire home is yours, including a private solar-heated pool, covered & screened patio w/ gas BBQ, fully equipped kitchen, 2 bedrooms w/ queen beds, 2 baths, garage & private washer & dryer. Generous side yard can securely store your RV or boat! Easy 15-20 min drive to public beaches or explore the surrounding areas like Sarasota & Fort Myers – all within an hour! Great price for a private pool & pet friendly home in the center of it all!

Guest favourite

Home in Punta Gorda

5 out of 5 average rating, 9 reviews

Paradise Waterfront Home near Fisherman's Village

This exceptional rental retreat is waterfront on the canal and features a saltwater heated pool. Nestled near the end of a tranquil street, it's a great place to stay with family and friends whether you are relaxing poolside, having a BBQ, fishing in the canal or travelling by foot or bike around PGI and Fisherman's Village. Many outdoor activities, beaches and parks nearby and tremendous dining options, or just stay in and enjoy the full kitchen with plenty of workspace and prep space.

Guest favourite

Home in Venice

4.92 out of 5 average rating, 119 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 shops, restaurants. Low-key quiet vacationers only. 2 car max. Login to your favorite streaming service with Smart TVs

Guest favourite

Home in Venice

4.91 out of 5 average rating, 181 reviews

Vacation Rental with private swimming pool

Located in a desirable community of South Venice. Venice, Manasota, Nokomis and Sharky’s beaches are located only 5 miles away. The historic Venice Avenue of unique shops, restaurants, special events. Farmer market, tennis courts, and children fountain are close by. Newly renovated home and swimming pool in a quiet peaceful area in an ideal place for any season gateway.A great place for biking, running and walking. My place great for couples, solo adventurers or families with kids.

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 heated 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 Punta Gorda

5 out of 5 average rating, 10 reviews

Stunning! Luxury waterfront home

STUNNING!! LUXURY WATERFRONT HOME - HEATED POOL- Close to Harbor/Fish Village -PREMIER HOST reviews averaging 5.0 since 2018 on other site. -Modern, newly updated home with open layout allowing for enjoyment of the cool waterfront breezes. -Boat dock with very close Harbor access within 10 minutes. -Southern exposure, full sun, heated pool, and waterfront. Oversized pool extends along large portion of rear of home.

Guest favourite

Home in Bradenton

4.88 out of 5 average rating, 125 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.

Guest favourite

Home in Sarasota

4.84 out of 5 average rating, 58 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