
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 R 480 ZAR per night before taxes and fees

Verified guest reviews
Over 6,110 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.

Private Pool | 20 min to Siesta Key4BR |Sleeps 12
Escape to Paradise Palms, a tropical, well equipped home with lots of room for fun and relaxation. Close to Siesta+Lido beaches! 5 miles to IMG +14 miles to AMI! 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.

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.

Serenity Lake
Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

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!

Beach Bliss: Open Sat - Fri, $175/nt + Fees!
This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Golf View-4BR Htd Pool/Near IMG/AMI/Siesta Beaches
Welcome to The Siesta Retreat located on Sarasota FL. This gorgeous home has been completely renovated in a peaceful area overlooking the Sara Bay Country Club Golf Course . Pack your bags and get ready to vacation! Home is 4 miles from SRQ Airport and 7 miles from downtown Sarasota. Siesta Key has been rated the #1 beach in the US, only 14 miles from the home. Additionally Ana Maria Island is 15 miles, Lido Beach 10 miles, Coquina Beach 13 miles, and Longboat Key 16 miles from home.

Sea Vue -King Beds | Stunning Views | 2MI to Beach
Welcome to Sea Vue, a luxury Western facing home offering unparalleled water views, superior outdoor living, 5 bedrooms with dreamy hotel style bedding and activities for the entire group. Located just 2 miles to award winning St. Pete Beach & a short drive to the booming Downtown area this home is sure to exceed guest's highest expectations. Prepare to experience the highest level of customer service and indulge in your own private oasis inside and out.

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.

Cozy Private Estudio • Near IMG, Beach & Airport
Cozy tropical retreat just 4.6 miles from Sarasota Airport and 7 miles from the beach. Perfect for two! Enjoy a private stock tank pool, fully equipped kitchen, comfy bed, fast Wi-Fi, and free parking. Relax in your own peaceful outdoor space and feel the tropical vibe. Ideal for a romantic escape, a beach weekend, or simply to unwind in a unique and private setting.
Popular amenities for Whitfield rentals with a pool
House rentals with a pool

Stylish 6 Bed Pool Home with Golf Simulator & Spa

Casa Noir | POOL • BBQ • FIRE PIT • GAMES • VIBES

Water's Edge: Charming Canal Oasis

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

Private Heated Pool~Yacht Rental~BBQ~Near Water

Heated Pool-Near Beaches-MiniGolf-Arcade

4BR Sarasota Retreat | Private Pool & Game Room!

Htd Pool + Games | Sleeps 12 | Near Lido & Siesta
Condo rentals with a pool

Beachfront Escape – Private Balcony, Gulf Views

The Beach Condo #107 Beachfront Full View

Beach Condo with Quiet, Private Beach

The Seashell Cottage with peaceful water views!

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

Cozy 2 bed/2.5 bath townhome

Sunset and beach view from your balcony Unit 403

Beachfront Resort, Ocean View, Pool, Tennis, Gym
Other vacation rentals with a pool

The Suite Retreat

Sarasota Studio | Pool | Near Siesta Key & Beaches

Pickleball/Heated Pool/Golf Front/Putt Green/BBall

Sara Bay Retreat

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Seashells & Sunshine – Pool, Games, AMI Beaches

Cottage on the canal

Top 5% of homes: Super clean, quiet, beach close
When is the best time to visit Whitfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 2,866 ZAR | R 3,699 ZAR | R 3,522 ZAR | R 3,346 ZAR | R 2,962 ZAR | R 3,026 ZAR | R 2,738 ZAR | R 2,466 ZAR | R 2,242 ZAR | R 2,210 ZAR | R 2,594 ZAR | R 2,914 ZAR |
| 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 |
Destinations to explore
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- Anna Maria Public Beach





