
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.

LUXE! Heated Salt POOL! Close to Town, Beach, IMG
Beautifully updated coastal farmhouse home in a quiet cul de sac with a private pool oasis in the back. The salt water pool is completely screened in so you can stay in the pool all day and night long without worrying about flies or mosquitos. Kitchen is fully stocked and ready for you to cook up a storm! Or if you prefer, downtown Sarasota is only a short 15 minute drive away with plenty of eating options. Siesta key beach is rated the number one beach in the USA and it’s only 30 minutes away!

Pool | Game Room | Fire Pit | Pet Friendly | 3 TVs
Our spacious single-level house is perfect for families or groups as it comfortably sleeps 10 people. The home features a renovated deep saltwater pool, an outdoor seating area with a BBQ grill, three 4K smart TVs with local channels (no cable), 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, biking and hiking trails. Minutes from downtown and blocks from the water.

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.

Pool house by the bay
Come stay in our beautiful, Mid-Century Modern, light drenched home just one block from the bay with a private pool. The private yard is surrounded by lush landscaping & the pool is the perfect place to cool off on hot afternoons. The house is spacious & minimally decorated with finds from our world travels. We've recently replaced the bed and the neighborhood is quiet and easy to explore on foot. Note: this is our home, so please expect a warm lived in feel in the space, not that of a hotel.

Free Early chk in 1 min-Ringling Campus, DT& Airpt
Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on a main road 1 mile from downtown Sarasota. Beside ARTS/DESIGN COLLEGE!! Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. This cornerr apartment with a dazzling wrap-around patio is your perfect getaway. 2. Bicycles. Send me a message if you have any questions .

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

Pool Courtyard, patio w/ fire pit, 2 mls downtown
Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

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.

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.

Luxury Family Home w/ Heated Pool Near Siesta Key
Prepare to be enchanted by your new sanctuary! Immerse yourself in luxury at this spacious and bright pool home, recently renovated to perfection. Located on a peaceful street, it strikes the perfect balance between tranquility and convenience, with easy access to Sarasota's finest attractions. Unwind at Siesta Key Beach, indulge in downtown's culinary delights and shopping, and explore the famous Fresh Fish Waltz Market—all just minutes away!

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.

Shorewalk full condo AnnaMaria Beaches IMG
1174 sqft Shorewalk condo with 2-bedroom, 2 bath , kitchen and living room unit on desirable ground level with a beautiful lake view Within very short walking distance to grocery ,movies, 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
Popular amenities for Whitfield rentals with a pool
House rentals with a pool

Gameroom +Private Pool+King Bed- Centrally Located

Oasis Villa Retreat Close to Beaches & IMG Academy

Pool! game room! Near Lido Key & Downtown Sarasota

Settle Down in Sarasota

Backyard Oasis, Dual Master suite, Pool home!

Priv Tropical Oasis | Pool+Golf+Bocce+Firepit+PETS

Orange Oasis: Clean, heated pool, near beaches.

Sunrise Villa - Tropical 3 bedroom home with pool
Condo rentals with a pool

SRQ/Longboat Key Beach - kid friendly/romantic B1

Shorewalk upgraded condo upstairs unit 4415

A&A's Paradise near IMG & Anna Maria beaches

Sunset and beach view from your balcony Unit 403

Anchor house +6 min. from Siesta Beach+heated pool

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Cozy 2 bed/2.5 bath townhome

New Luxury 3/3 Condo in Margaritaville Resort
Other vacation rentals with a pool

Family Fun w/Pool •Fire pit• Arcade• 9 miles Beach

The Ellenton Getaway

1 lvl w large htd pool, 4 bd(3 king), remodeled!

Resort Style Home w/ Hot tub

Coastal Oasis/big pool heat option / 3bd2bth house

Fantastic 1 bed/1bath on IMG Campus!

3bd/3ba on water - Pool - Dock your boat

Cozy Beach House Including King Size Suite !
When is the best time to visit Whitfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ632 | ﺩ.ﺇ859 | ﺩ.ﺇ841 | ﺩ.ﺇ632 | ﺩ.ﺇ577 | ﺩ.ﺇ551 | ﺩ.ﺇ628 | ﺩ.ﺇ566 | ﺩ.ﺇ514 | ﺩ.ﺇ668 | ﺩ.ﺇ650 | ﺩ.ﺇ657 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about vacation rentals with a pool in Whitfield

Total vacation rentals
Explore 110 vacation rentals in Whitfield

Nightly prices starting at
Whitfield vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 4,830 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
110 of Whitfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Whitfield rentals

4.8 Average rating
Whitfield stays are highly rated by guests—averaging 4.8 out of 5!
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