Vacation rentals with a pool in Winter Springs

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winter Springs

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guesthouse in Longwood

4.97 out of 5 average rating, 113 reviews

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not have issues. Grab bars in the bathroom.

Top guest favorite

A spacious swimming pool is surrounded by a tiled patio, with lounge chairs placed nearby. Lush green lawns and trees frame the area, offering views of the tranquil lake in the background. A shaded pavilion is visible to one side, providing a relaxing outdoor space.

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 363 reviews

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Top guest favorite

A round above-ground pool is surrounded by a stone pathway and a grassy area. A blue shade sail is positioned overhead, offering protection from the sun. A swing set is located nearby, enhancing the outdoor recreational space.

Home in Longwood

4.96 out of 5 average rating, 141 reviews

Pvt Fishing lk , Pets,Nature, Pool,garage

No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes and kayak, peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions NEW SHOWS at DISNEY close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

Guest favorite

A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.

Home in Maitland

4.87 out of 5 average rating, 128 reviews

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Guest favorite

Home in Casselberry

4.88 out of 5 average rating, 107 reviews

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

Newly renovated farmhouse gem centrally located in the beautiful Casselberry / Orlando area. Stylish and thoughtful touches throughout will make you feel right at home. 2 king beds, 1 queen and 1 bunk room (2 doubles & 2 twins) along with an 8' farmhouse table (seats 8) makes this home great for both small & larger groups alike. Complete with a hot tub, amazing walk-in shower, Marvel Arcade, Private patio with pergola outdoor furniture & Pool, it's great for both the adults and kiddos!

Top guest favorite

A tranquil pool area is surrounded by a screened enclosure, showcasing a crystal-clear saltwater pool. Comfortable lounge chairs are positioned near the water, and lush greenery, including ferns and tropical plants, enhances the serene setting.

Guest suite in Lake Mary

4.96 out of 5 average rating, 347 reviews

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Top guest favorite

A private outdoor pool area is highlighted, featuring a clear blue pool surrounded by patio tiles. Comfortable lounge chairs and a dining set under large umbrellas offer shaded seating. Lush greenery forms a natural backdrop, enhancing the tranquil atmosphere.

Guest suite in Oviedo

4.92 out of 5 average rating, 427 reviews

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and there is no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge, microwave, TV, Wifi and access to non-heated swimming pool. Host primary residence does overlook the pool area. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Disney: 40 miles

Superhost

A screened-in pool features a curvy design, surrounded by a spacious deck. The water is clear and inviting, reflecting sunlight. Lush greenery and tropical plants are visible around the pool area, creating a serene outdoor environment.

Home in Altamonte Springs

4.82 out of 5 average rating, 131 reviews

Quiet Place, convenient to everything!

Spacious home in a very quiet residential neighborhood. Perfect home away from home for your special getaway. Vacations, business trips, wedding groups, graduations have all been hosted in the past, and everyone had a great time. There's significant value in having your own quiet place and multiple rooms in a family-friendly setting. DO NOT BOOK MY QUIET PLACE IF YOUR PLAN INCLUDES ANY LARGE GATHERING WHICH MIGHT IMPACT MY HOME OR NEIGHBORHOOD. YOUR RESPECT IS EXPECTED.

Guest favorite

A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.

Home in Lake Mary

4.89 out of 5 average rating, 266 reviews

Gated community XL pool Home 2500sq/f

Our LK Mary home sits in Between the 2 most famous places central Florida has to offer, Disney World & Daytona beach and everything else in between. This property sits on 1/2acre of land, tropical landscaped backyard making your stay with us the true Floridian experience . Total privacy with quite nights for a full rest. NO BIKERS PLease! My home is in a Gated community.1 mile to Dtwn Lake Mary. Our pool is NOT heated, the hot tub only CAN be headed at an additional cost

Top guest favorite

A salt-water pool is visible, featuring distinct areas with glowing blue and green lighting, set against a backdrop of a vibrant sunset sky. Surrounding the pool is a textured stone patio and a secure fence, providing a tranquil outdoor space.

Guesthouse in Orlando

4.99 out of 5 average rating, 161 reviews

Luxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

Superhost

A well-maintained outdoor pool is surrounded by a stone patio, with lounge chairs positioned for relaxation. The area is enhanced by palm trees and greenery. Behind the pool, an inviting clubhouse with large windows is visible, offering a shaded retreat.

Condo in Winter Park

4.83 out of 5 average rating, 106 reviews

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

Top guest favorite

A rustic stock tank pool is positioned on a stone pathway surrounded by natural landscaping. Comfortable seating with blue-patterned cushions is visible next to the pool, alongside a hammock and shed. The area is shaded by a canopy, providing a relaxing outdoor space.

Home in Sanford

4.99 out of 5 average rating, 150 reviews

The Cypress House

This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb