Vacation rentals with a pool in Whitfield

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Whitfield

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

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Guest favourite

Home in Sarasota

4.89 out of 5 average rating, 117 reviews

POWER ON! Pool+outside lounge+TV+Sleeps 12!

Escape to Paradise Palms, a tropical, well equipped home with lots of room for fun and relaxation. This spacious property boasts a great layout for groups including a large dining area with seating for 8 comfortably and a fully equipped kitchen.Step outside into the fully screened lanai area with a lounge area with a 60'' TV, dining table with seating for 6, fenced yard and a large pool with plenty of pool toys for your enjoyment. Close to Siesta+Lido beaches! 5 miles to IMG +14 miles to AMI!

Guest favourite

Rental unit in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 160 reviews

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

Guest favourite

Condo in Lido Key

4.96 out of 5 average rating, 132 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

**No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, There is a pull-out large kitchen table. Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Guest favourite

Guesthouse in Sarasota

5 out of 5 average rating, 151 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Guest favourite

Condo in Bradenton

4.95 out of 5 average rating, 149 reviews

The Seashell Cottage with peaceful water views!

Hello and welcome to my beautiful Seashell Cottage! I have completely renovated and remodeled this townhome for you! It has a new kitchen and bathroom, new vinyl plank flooring upstairs, new furniture and bedding throughout, and is freshly painted. Decorated in a turquoise beachy decor, it gives you a sense of peace and tranquility the moment you step inside! There are gorgeous water views of the lake from both the first and second floor. Enjoy your private hammock on a seashell beach!

Superhost

Home in Bradenton

4.86 out of 5 average rating, 146 reviews

Resort Style Backyard Oasis w/Heated Pool/Tiki Bar

The home was untouched from hurricane. I have power and everything works from Milton. The Pool is in good shape. This gorgeous home has been completely renovated with an OPEN Concept layout, Brand New Salt Water Heated Pool, and Tiki Bar w/ Wet bar, 50 TV W/ NFL Ticket! Located 5 Minutes from IMG Academy and 15 Minutes from Beaches, 5 miles from SRQ airport and 10 min to downtown Bradenton and Sarasota. HIGH Speed WiFi! FREE Off Street Parking! YoutubeTV w/ NFL Ticket poolside!

Guest favourite

Condo in Bradenton

4.95 out of 5 average rating, 120 reviews

Cozy 2 bed/2.5 bath townhome

Renovated 2 bedroom/2.5 bathroom townhome nestled in a quiet, gated community in Bradenton between I-75 & some of the best beaches in the country. My townhome is 2 bedrooms (queen size) with en suite bathrooms. The beds are queen-sized. Amenities in the neighborhood include large heated pool, tennis and basketball courts, a playground, a volleyball area, a sports field, and a designated parking spot only steps away from the front door. Non-numbered guest parking is also available

Guest favourite

Guesthouse in Sarasota

4.88 out of 5 average rating, 199 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Guest favourite

Rental unit in Indian Beach-Sapphire Shores

4.97 out of 5 average rating, 112 reviews

Free Early Chk-in, Super Clean, New apt/bldg.

Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on the main road 1 mile from downtown Sarasota. Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Just a stone's throw away from downtown Sarasota, Lido Beach, and essential amenities like grocery stores and pharmacies, our corner apartment with a dazzling wrap-around patio is your perfect hideaway. Bicycles at your disposal. Book now

Guest favourite

Cottage in Bradenton

4.96 out of 5 average rating, 106 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

Superhost

Home in Sarasota

4.82 out of 5 average rating, 162 reviews

☀ Pet and Family Friendly Home with Pool ☀

Our spacious single-level house is perfect for families as it comfortably sleeps 10 people. The home features a renovated caged pool, an outdoor seating area with a BBQ grill, three 4K smart TVs, a game room and a fire pit. The backyard is fenced and well-behaved dogs are welcome. We are a short drive away from some of the best beaches in the country, amazing kayaking, bike riding and hiking trails. The pool can be heated up to 78-82F for an extra charge ($25/day).

Guest favourite

Guest suite in Bradenton

5 out of 5 average rating, 216 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.