
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.

Tropical Sarasota Oasis | Private Pool + 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.

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt
Beach ready Apt!! Echo/white noise machine 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 .

A&A's Paradise near IMG & Anna Maria beaches
Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

The Animal House
Relax with the whole family at this peaceful place to stay. Fun animal themed, totally remodeled upstairs apartment with one bedroom and kitchen. Private entrance and on driveway parking. Private screened lanai upstairs with outdoor dining and room for family games or entertaining. Access to the pool and lanai (newly renovated), fire pit, treehouse, swing and your own gas grill for guest use. Spacious back yard on a cul-de-sac. Close to shopping, dining, beaches, the airport and the interstate.

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.

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.

Beachfront Resort, Ocean View, Pool, Tennis, Gym
Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

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.

Private Heated Pool, Turfed Putting Green Retreat
Imagine life in a tropical oasis-surrounded by palms trees, turfed lawn and putting green while enjoying the Florida sun relaxing your private saltwater heated pool with extended sun shelf. This 3 bedroom/2 bath 1940s bungalow is a great place to relax and unwind with your own resort style backyard. The fully equipped home, located between downtown Bradenton and Anna Maria Island offers fun in every direction. We guarantee you'll want to stay awhile!

Sweet Retreat at Shorewalk!
Bring the whole family to this great place with lots of room for fun. A spacious 2 bedroom, 2 bathroom condo on the second floor, newly renovated and fully equipped, is within walking distance of supermarkets, restaurants, the cinema, and bowling. Whether you are a single family on vacation, a couple enjoying a weekend getaway, or a sports team in training, we have you covered. Stay with us and enjoy all the comforts of home!
Popular amenities for Whitfield rentals with a pool
House rentals with a pool

Waterfront View Mins To AMI Beaches

Seashells & Sunshine – Pool, Games, AMI Beaches

Coastal Oasis/big pool heating option /3bd2bth

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

The Sea Hut

Heated Pool-Near Beaches-MiniGolf-Arcade

Cozy Pool House| 24 min to Beach

Heated 3BR Pool Home Glen Oaks | Close to Downtown
Condo rentals with a pool

Palms Villa: Cozy & Minutes from Anna Maria Island

Shorewalk upgraded condo 4505.

Sunset and beach view from your balcony Unit 403

Cozy 2 bed/2.5 bath townhome

The Seabreeze Cottage with peaceful water views

Sun-Kissed Memories!

Sea Club 2 - Relaxing Siesta Beach Key Condo Rental

Short Stroll to the Surf! ~ Make Memories on AMI
Other vacation rentals with a pool

Waterside Retreat: Modern 2BR, Mins to Beach & Apt

Freshly Renovated Vacation Villa at Shorewalk

Hotel Style w/pool & Tiki Grill

Settle Down in Sarasota

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

Beautiful Top Floor Serenata 2Bd/2Ba Apartment

Modern Beach Haven: Secure Suite @ IMG Academy

Luxury 2BR/2BA Condo Minutes from Beaches & IMG
When is the best time to visit Whitfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $235 CAD | $320 CAD | $313 CAD | $235 CAD | $215 CAD | $205 CAD | $234 CAD | $211 CAD | $191 CAD | $189 CAD | $222 CAD | $249 CAD |
| 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 120 vacation rentals in Whitfield

Nightly prices starting at
Whitfield vacation rentals start at $41 CAD per night before taxes and fees

Verified guest reviews
Over 5,130 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
120 of Whitfield vacation rentals include wifi access

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

4.7 Average rating
Whitfield stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Rentals with a washer and dryer Whitfield
- Waterfront rentals Whitfield
- Fitness-friendly rentals Whitfield
- Family-friendly rentals Whitfield
- House rentals Whitfield
- Pet-friendly rentals Whitfield
- Rentals with outdoor seating Whitfield
- Rentals with a firepit Whitfield
- Rentals with a fireplace Whitfield
- Hotel rooms Whitfield
- Rentals with a patio Whitfield
- Rentals with pools Manatee County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Dunedin Beach
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- Manasota Key Beach
- River Strand Golf and Country Club
- Hard Rock Casino
- Englewood Beach
- North Beach At Fort DeSoto Park




