
Vacation rentals with a pool in Whitfield
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Whitfield

Total vacation rentals
Explore 120 vacation rentals in Whitfield

Nightly prices starting at
Whitfield vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

Verified guest reviews
Over 5,610 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
120 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!
Top-rated rentals with a pool in Whitfield
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Cozy Beach House Including King Size Suite !
Welcome to our beach home ! Located in a beautiful neighborhood where you can unwind & relax with the family after a long day at the beach. We are located only a short drive to the finest beaches in FL where you can find sand dollars with the kids & view breathtaking sunsets ! Play a game of pool, grill out on our patio, & enjoy our fire pit & enclosed pool !! This easy access one-level home sleeps up to 8 people. Conveniently located within minutes from groceries, restaurants, and attractions.

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.

Free Prkn, Early Chkin, Elevator-4th fl airport/DT
Beach ready Apt!! Perfect for work trips! Beside Ringling College! 2 minutes from downtown Sarasota 7 mins - Airport Corner Apt Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb that's on a main road . 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches
Get ready for nonstop fun at Paradise Island - an amenity-packed retreat in Sarasota! Whether you're in the heated pool or hot tub, playing mini golf, enjoying a family game night, relaxing by the fire pit, or grilling barbecue in the backyard, there’s something here for everyone. This vibrant 4-BR, 2-bath home sleeps up to 14 guests and is just 5 minutes from the airport and a short drive to world-class beaches. BOOK YOUR STAY TODAY - The Ultimate Retreat for Family Fun and Forever Memories

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

Sarasota Oasis: Convenient/Heated Renovated Pool
Welcome to Coastal Serenity, your perfect Sarasota escape! This charming, fully remodeled coastal home is designed with relaxation and fun in mind. Just three blocks from the breathtaking Sarasota Bay and only a few miles from stunning beaches like Siesta Key, Lido Key, Bradenton Beach, and Anna Maria Beach, it’s an ideal location for beach lovers. Plus, you’re only steps away from vibrant tiki bars and luxurious Sarasota restaurants, perfect for unwinding in a relaxed, inviting atmosphere.

Htd Pool | PingPong | Foosball | 12 min to Beach
Welcome to Coastal Farmhouse Sarasota! ✨ Your ideal family getaway is just two blocks from Sarasota Bay and minutes from Florida’s most famous beaches Siesta Key, Lido Key, Bradenton Beach, and Anna Maria Island. Designed with families and groups in mind, this newly remodeled 4-bedroom home sleeps up to 12 guests and features a screened heated pool, a fully equipped kitchen, and a bright, open layout perfect for relaxing and entertaining. Perfect for families, groups, and beach lovers!

Sarasota Studio|Heated Pool|Near Siesta Key & IMG
Coastal marina calm meets boutique hotel vibes on Sarasota Bay. This privately owned studio condo is located within a hotel property and operates as an independent Airbnb unit. Sleeping arrangement includes a queen bed and sofa sleeper in the studio. Minutes from beaches & IMG. Hidden gem. Located on Ramada By Wyndham property with bar, boat rentals, pool and 3 minutes from SRQ. Perfect for IMG coaches, athletes, and travelers. Private jet services nearby. Sunset Views and free parking.

Pool, Shuffleboard, EV charg, Near beach, UTC mall
Welcome to Vistalodgings Vista Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

Luxury Pool Family Oasis-Siesta Beach Beac-3BR/2BA
Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into a luxurious experience the minute you arrive. Located on a lush quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

Bayside*Htd pool*Pickleball*Close to Beaches
Welcome to Sarasota Bayside! This 3 bedroom 2 bath home sleeps 7 comfortably. Guests will find 1 bedroom with 2 twin beds, another with 1 queen bed and the primary en-suite has a king bed. There's also a daybed room just off the living room. The heated pool and game table in the garage, board games, proximity to beaches, IMG, and so much more make this home a terrific choice for your Sarasota stay!

Paradise Escape w/ Pool, Sarasota/Bradenton
Take it easy at this unique and exciting getaway, located 5 minutes from the Sarasota airport (airplanes fly over), 12 minutes from downtown Sarasota, and 15 minutes from Lido Key beach. Enjoy a refreshing dip in the outdoor pool and/or take a walk to the waterfront (2 blocks over) to watch the sunset. Your furry friends are welcome, there is a large fenced in backyard to accommodate pets.
Popular amenities for Whitfield rentals with a pool
House rentals with a pool

Retreat by the Bay-Heated Saltwater Pool

Water's Edge: Charming Canal Oasis

5BR/4BA |Pool & Spa + Pickleball, Golf View

Siesta Key Beach Getaway

Seashells & Sunshine – Pool, Games, AMI Beaches

Heated Pool-Near Beaches-MiniGolf-Arcade

The sun is shining at SunSota-Htd Pool/Game RM/MCM

Sapphire Shores Muse | 2 Bed 3 Bath | Luxe Pool
Condo rentals with a pool

The Beach Condo #107 Beachfront Full View

On the Beach; Siesta Key SunBum Studio

LIDO KEY 1 BR/1Bath Heated Pool 16

Sunset and beach view from your balcony Unit 403

Cozy 2 bed/2.5 bath townhome

Heated Pool Apartment Near Siesta Key | 1BR

Beachfront Resort, Ocean View, Pool, Tennis, Gym

The Seabreeze Cottage with peaceful water views
Other vacation rentals with a pool

4BR Sarasota Retreat | Private Pool & Game Room!

Backyard Oasis, Dual Master suite, Pool home!

Pickleball & Heated Pool | Pets Welcome Retreat

Private Pool Oasis w/ Golf Course Sunsets

Near Beaches! + Canal, Pool, and Vibrant Downtown!

Pool+Hot Tub | Coffee Bar | Volleyball | Location

Ponderosa Pine-*Family Friendly*Near airport*Pool*

Clean, quiet, 3 miles from SRQ, 15% off July 26-30
When is the best time to visit Whitfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 657 | ﺩ.ﺇ 848 | ﺩ.ﺇ 808 | ﺩ.ﺇ 632 | ﺩ.ﺇ 577 | ﺩ.ﺇ 551 | ﺩ.ﺇ 628 | ﺩ.ﺇ 566 | ﺩ.ﺇ 514 | ﺩ.ﺇ 507 | ﺩ.ﺇ 595 | ﺩ.ﺇ 668 |
| 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 |
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