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, 116 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

Home in Bradenton

4.93 out of 5 average rating, 134 reviews

Endless Outdoor FUN! Pool/Spa/Golf/Games/Near IMG.

Make memories at this unique, FUN, family friendly place. Let The Sunshine House fill you with joy! This happy 3 bed/2 bath home will have you and your guests smiling from ear to ear with the beautiful decor. Fully stocked for the beach (only 6 MILES away) or stay &enjoy the amenity-rich backyard with <b>turf, putting green, heated pool, hot tub, grill, stone fire pit, yard games& lots of fun photo ops!</b> At night this place is even more jaw dropping w/colorful lights. Leaving will be tough.

Guest favourite

Home in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 142 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

Guest favourite

Guesthouse in Sarasota

5 out of 5 average rating, 147 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

Superhost

Home in Bradenton

4.86 out of 5 average rating, 145 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, 119 reviews

Newly remodeled 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

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.

Guest favourite

Condo in Bradenton

4.97 out of 5 average rating, 122 reviews

The Seabreeze Cottage with peaceful water views

Welcome to my newly renovated townhouse! The Seabreeze Cottage is a two bedroom, 1.5 bath, colorfully decorated townhouse with a fun beachy vibe! It has beautiful and peaceful water views of the lake. It’s within 30 minutes of the Gulf Coast’s best beaches, including Anna Maria Island, Longboat Key, and Siesta Key. Only ten miles from Sarasota airport (SRQ) and about one hour from Tampa airport (TPA). It’s just 7 miles or 15 min from the world renowned IMG Academy.

Superhost

Home in Sarasota

4.82 out of 5 average rating, 160 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

Condo in Bradenton

4.98 out of 5 average rating, 190 reviews

Shorewalk full condo IMG Beaches Anna Maria

1174 Sqft first floor 2 bedroom and 2 bathroom with a nice kitchen full condo in the beautiful Shorewalk community. Within very short walking distance to movies, groceries ,shopping and dining This condo is about 9 miles from Sarasota airport and about 13 miles from downtown Sarasota, about 6.8miles from the Bradenton Beach , about 10 miles from Anna Maria Island Less than 1 mile to the big gate of the IMG academy

Guest favourite

Guest suite in Bradenton

5 out of 5 average rating, 214 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.