Vacation 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 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

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.

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.

4.99 out of 5 average rating, 317 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.

4.93 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.

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

A beautiful and private one bedroom cottage in a 1924 built Ringling property, nestled in the historic neighborhood of Whitfield a estates. With everything you would need including a semi private not heated pool, private parking and separate entrance. A ten minute drive to downtown Sarasota, 15 to Lido beach/St. Armamds circle, three minutes from Sarasota airport and 5 minutes to all of the shopping University place has to offer! Please follow us @casitafloreado #casitafloreado

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

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 123 reviews

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

Home in Bradenton

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

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!

5.0 out of 5 average rating, 9 reviews

Home in Bayshore Gardens

King Beds | Game Room | Putt Putt | Pool |

5.0 out of 5 average rating, 3 reviews

The Aviator | 7 Mins From SRQ | Pool | Giga Wifi

4.96 out of 5 average rating, 25 reviews

Pool, pickleball and games! Relax in our home

4.98 out of 5 average rating, 64 reviews

Grand Sarasota Retreat:Heated Pool • Beach • Patio

4.89 out of 5 average rating, 55 reviews

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

5.0 out of 5 average rating, 73 reviews

Seashells & Sunshine – Pool, Games, AMI Beaches

Condo rentals with a pool

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!

4.98 out of 5 average rating, 258 reviews

Condo in Longboat Key

Island Time: Open Next Week!

4.88 out of 5 average rating, 139 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

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, 144 reviews

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

The image captures a serene beach scene at sunset, with a golden sun reflecting on the gentle waves. Silhouetted seagulls stand in the sand, their shadows stretching across the shoreline as the day's warmth begins to fade.

4.9 out of 5 average rating, 115 reviews

Serene 2 Bedroom Condo in ShoreWalk Resort

A modern kitchen showcases sleek, white cabinetry and a dark granite countertop. Stainless steel appliances include a microwave and oven, complemented by a mosaic tile backsplash. The space is well-lit with natural light from an adjacent living area, creating an open and airy environment.

4.79 out of 5 average rating, 155 reviews

Shorewalk upgraded condo 4505.

4.98 out of 5 average rating, 110 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

4.91 out of 5 average rating, 152 reviews

New Luxury 3/3 Condo in Margaritaville Resort

Other vacation rentals with a pool

4.9 out of 5 average rating, 20 reviews

Condo in Sarasota

Sarasota Studio | Pool | Near Siesta Key & Beaches

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 screened-in outdoor area features a sparkling pool surrounded by tan brick pavers. Four white lounge chairs are positioned near the water, and the light blue sky complements the home's beige exterior and vibrant blue doors.

4.92 out of 5 average rating, 92 reviews

4BR Sarasota Retreat | Private Pool & Game Room!

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

4.68 out of 5 average rating, 137 reviews

A pelican is perched on a wooden railing overlooking the ocean, with its long beak prominently displayed. The water reflects gentle waves beneath a cloudy sky, while a sign stating 'No Sitting or Standing on Rails' is positioned below the bird.

Condo in Sarasota

Hotel Style w/pool & Tiki Grill

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

The vibrant outdoor space features a mini-golf putting green, surrounded by strategically placed lounge chairs and Adirondack seating. Illuminated by string lights, the heated pool area is complemented by cabana umbrellas, with a backdrop of the house showcasing lively decor and inviting lighting.