Holiday rentals with a pool in Whitfield

4.82 out of 5 average rating, 101 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and decorative rocks. Palm trees and various plants enhance the area, while the tranquil water view is visible in the background, providing a calming atmosphere for relaxation.

Loft in Bradenton

Mediterranean-Type Waterfront w/Pool-Saltwater Spa

Kick back in this Scent of Serenity Retreat. This 3-Level Private 2-Bedroom/1 Bath apartment/loft sleeps up to 5 guests. Pool-Saltwater Spa. Recreation Rm. Shared Laundry Rm in bldg. Level 1: Twin Bed sleeps 1 Lev. 2: Master Queen Bed for 2; Lv Rm: Futon Sleeps 1 ; Air mattress sleeps 1 Lev.3-Observation/Yoga Rm. Spiral Staircase. No wheelchair access. Not suitable for kids under 12. 10mins from SRQ. Botanical gardens, shopping, restaurants - 1-2 mi. Beaches w/Free parking 9 mi away.

4.93 out of 5 average rating, 129 reviews

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.

A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.

4.97 out of 5 average rating, 105 reviews

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indulge at this Mediterranean estate, boasting lush botanical gardens and rare tropical fruit trees for your picking pleasure. Enjoy the custom pool, hot tub, sauna, cold plunge and the home gym. The expansive outdoor haven features a fully-equipped kitchen, fireplace, TV, and dining space. Enjoy leisurely games of pool, ping pong & shuffleboard, then retreat to the luxurious indoors with comfortable beds and a massive TV, all within the privacy of a walled-in estate. Your lavish escape awaits.

The covered swimming pool area features a spacious rectangular pool with crystal-clear water. Surrounding the pool are several lounge chairs, and the area is framed by a screened enclosure. Landscaped borders enhance the outdoor space with a touch of greenery.

4.82 out of 5 average rating, 224 reviews

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.

4.98 out of 5 average rating, 104 reviews

A cozy living area features a light blue wall, with a comfortable white sofa arranged around a neutral-toned rug. In the foreground, a wooden dining table with four chairs provides seating. Natural light enters through a doorway that leads to an outdoor space.

Guesthouse in Bradenton

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.

4.98 out of 5 average rating, 318 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Sarasota

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

A screened patio area features a private heated pool, surrounded by lush greenery. Comfortable seating includes wooden chairs and a table, with lounge chairs positioned by the pool. Bright sunlight fills the space, creating a welcoming atmosphere for relaxation.

4.96 out of 5 average rating, 112 reviews

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!

4.85 out of 5 average rating, 108 reviews

A spacious outdoor area features a heated saltwater pool surrounded by a screened enclosure. A jacuzzi is attached to the pool, with multiple lounge chairs positioned for relaxation. Lush greenery lines the perimeter, enhancing the sense of privacy and tranquility.

Home in Bradenton

Stylish 6 Bed Pool Home with Golf Simulator & Spa

Experience ultimate Florida luxury at our 6-bedroom, 4-bathroom Bradenton home, fully remodeled for your perfect staycation. Enjoy a heated saltwater pool, spa, outdoor kitchen, and bar with granite counters, ice maker, and fridge. Nestled at the end of a private drive, this paradise offers a golf simulator, putting green, and cornhole court. Centrally located yet secluded, it comfortably sleeps 12. Non-smoking and meticulously clean, this is your dream getaway for relaxation and fun.

4.97 out of 5 average rating, 103 reviews

The inviting pool area features a vibrant mural, surrounded by tropical greenery. A floating flamingo and watermelon-shaped inflatable add a playful touch to the azure water. Colorful poolside seating, including cheerful yellow chairs, enhances the relaxing atmosphere of this outdoor space.

Home in Bradenton

Near IMG! Fun 4BR•Pool w/Golf, Arcade & Fire Pit!

Welcome to SunKissed Getaway! A bright and spacious family-friendly pool home designed for comfort, fun, and relaxation. Perfect for families, groups, and IMG visitors, this home offers a private pool, cozy fire pit, BBQ station, mini golf, arcade games and outdoor games everyone will love! Perfectly located just 3 miles from SRQ Airport, close to IMG Academy, Sara Bay Golf Club, and the best Gulf Coast beaches including Anna Maria Island, Lido Beach, Bradenton Beach, and Siesta Key.

4.93 out of 5 average rating, 113 reviews

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.

The image features a heated saltwater pool with a pink inflatable flamingo. Surrounding the pool are comfortable seating options, including fire pit seating. The vibrant indoor spaces are visible, showcasing a cozy living room with a turquoise color scheme and a game room with a retro arcade machine.

4.98 out of 5 average rating, 110 reviews

Family Oasis *Heated Saltwater Pool *Near Beaches

Welcome to ☀️ Sarasota Sunshine ☀️ — your family's home away from home! Relax by your private heated pool, spend the day at nearby Gulf Coast beaches, or visit downtown Sarasota from our thoughtfully designed home. Sleeping up to 9 guests, Sarasota Sunshine offers modern comfort and extensive family-friendly amenities, making it easy to pack less, relax more, and create lasting memories. Minutes from downtown Sarasota, SRQ Airport, IMG Academy, and world-famous Gulf Coast beaches.

A charming one-level home is presented, surrounded by lush tropical landscaping. The exterior features a welcoming entrance with a decorative lantern and a garage, set against a backdrop of a colorful sunset sky, enhancing the inviting atmosphere of the property.

4.96 out of 5 average rating, 129 reviews

Double oven | 4 Famous Beaches | Wine Fridge

Escape to The Bay 218, a beautifully updated one-level Sarasota retreat just steps from the bay and minutes from Lido Key, Siesta Key, Longboat Key, and Anna Maria Island. Relax by your private heated pool, enjoy the chef's kitchen, spacious living areas, and comfortable bedrooms, or head to the beach with the included chairs, cart, and toys. Perfect for families, friends, and coastal getaways. Dog-friendly with approval.

Popular amenities for Whitfield rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A screened lanai area features a glistening pool surrounded by a spacious deck. Two cushioned lounge chairs are positioned for relaxation. Lush palm trees frame the view, complementing the tranquil setting of the fenced backyard.

4.89 out of 5 average rating, 159 reviews

Private Pool | 20 min to Siesta Key4BR |Sleeps 12

An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.

4.95 out of 5 average rating, 110 reviews

Retreat by the Bay-Heated Saltwater Pool

4.96 out of 5 average rating, 25 reviews

Pool, pickleball and games! Relax in our home

5.0 out of 5 average rating, 74 reviews

Seashells & Sunshine – Pool, Games, AMI Beaches

A collage showcases key areas of the property, including a spacious pool area with loungers, a game room equipped with a pool table and foosball, a cozy living room with a fireplace, and an outdoor space featuring a relaxed atmosphere surrounded by greenery.

4.93 out of 5 average rating, 73 reviews

Sarasota Oasis: Convenient/Heated Renovated Pool

A large outdoor pool is framed by mature tropical landscaping, featuring a clear blue water surface under a bright sky. Lounge chairs are positioned around the pool area, providing ample seating for relaxation and enjoyment.

5.0 out of 5 average rating, 50 reviews

Backyard Oasis, Dual Master suite, Pool home!

4.97 out of 5 average rating, 39 reviews

Private Heated Pool~Yacht Rental~BBQ~Near Water

5.0 out of 5 average rating, 9 reviews

Home in Bayshore Gardens

King Beds | Game Room | Putt Putt | Pool |

Condo rentals with a pool

4.98 out of 5 average rating, 258 reviews

Condo in Longboat Key

Island Time: Open Tues - Sat!

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

4.97 out of 5 average rating, 145 reviews

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

A cozy lanai features a view of the tranquil lake, with vibrant turquoise chairs arranged around a patterned rug. Potted plants add greenery, while large glass doors provide natural light and an outdoor connection.

4.95 out of 5 average rating, 212 reviews

The Seashell Cottage with peaceful water views!

4.88 out of 5 average rating, 139 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

An open kitchen features a dark granite countertop with seating for two. A set of pendant lights hangs above, illuminating the space. Modern appliances and warm wood cabinetry create a functional cooking area. A welcoming sign is displayed on the wall near the laundry machines.

4.87 out of 5 average rating, 152 reviews

Shorewalk upgraded condo upstairs unit 4415

The inviting living area features a brown leather sofa paired with a teal accent chair. A circular mirror is positioned above a coffee table, which holds magazines. A patterned rug sits beneath, and natural light filters through the sliding glass doors.

4.96 out of 5 average rating, 161 reviews

Cozy 2 bed/2.5 bath townhome

4.98 out of 5 average rating, 110 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

4.97 out of 5 average rating, 212 reviews

Luxury 3/3 Margaritaville Resort

Other holiday rentals with a pool

4.93 out of 5 average rating, 30 reviews

A charming yellow cottage is shown surrounded by lush greenery. The exterior features arched windows and a terrace area furnished with blue chairs and a table, complemented by a striped umbrella. Flower arrangements add a touch of color to the vibrant setting.

Guesthouse in Sarasota

Casita Floreado! Private 1BR cottage, with pool

4.9 out of 5 average rating, 20 reviews

Condo in Sarasota

Sarasota Studio | Pool | Near Siesta Key & Beaches

A private screened pool area features a vibrant blue pool surrounded by loungers and colorful pool floats. A well-maintained lawn and mini-golf area are visible, while a game room with bright visual elements offers entertainment options. A cozy living space showcases a comfortable sofa and artistic wall design.

4.91 out of 5 average rating, 77 reviews

Heated Pool-Near Beaches-MiniGolf-Arcade

Place to stay in Sarasota

A cozy seating area is featured with a modern electric reclining loveseat and a small bar table with two stools. Light from a nearby lamp provides illumination, while decorative artwork and a sign add a touch of charm to the neutral walls.

The Suite Retreat

4.84 out of 5 average rating, 58 reviews

A serene outdoor area features two lounge chairs beside a small table, surrounded by lush palm trees. The clear water of the canal reflects the blue sky, while a screened enclosure contains a swimming pool nearby, creating a tranquil setting for relaxation.

5.0 out of 5 average rating, 44 reviews

Water's Edge: Charming Canal Oasis

A spacious outdoor area features a clear pool surrounded by lush greenery and palm trees. Lounge chairs are arranged beside the pool, and a playset is visible in the background. Neatly laid stepping stones lead towards the grass, enhancing the inviting environment.

4.97 out of 5 average rating, 93 reviews

As seen on HGTV | 6 miles to the beach! Htd pool

4.88 out of 5 average rating, 8 reviews

Bayside*Htd pool*Pickleball*Close to Beaches