Vacation rentals with a pool in Winter Springs

Find and book unique homes with a pool on Airbnb

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Popular amenities for Winter Springs rentals with a pool

House rentals with a pool

Guest favorite
The in-ground swimming pool, shaped in a natural curve, is surrounded by a red deck and lush greenery. Pool toys and a basketball hoop are visible, alongside lounge chairs, providing space for relaxation and enjoyment.
Home in Orlando
4.88 out of 5 average rating, 124 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

SuzanneRating, 5 stars5 days ago
Had a nice stay with family and friends at Alyssa’s place along with 2 dogs. Was so nice to be able to bring out pets along on vacation. The house was clean, beds were comfortable, lots of space. I Spent most of my time out in the pool which was amazing.
Top guest favorite
The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.
Home in Kissimmee
4.87 out of 5 average rating, 241 reviews

3 bedroom Villa in Kissimmee

JenniferRating, 5 stars3 weeks ago
I cannot say enough good things about Raymond & our stay. I travel a lot for my son’s lacrosse team & this was our favorite Airbnb so far! Raymond is very responsive & kind! I hope it’s available to book next year when we return.
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, 129 reviews

Quiet Place, convenient to everything!

FrancisRating, 5 stars1 month ago
The home is as described. Nice and Clean. Quiet neighborhood. Highly Recommend!!!!
Top guest favorite
A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.
Home in Orlando
4.99 out of 5 average rating, 135 reviews

Private pool home near Downtown

VanRating, 5 stars2 weeks ago
Great house. Great host. Always attentive and responsive. 2nd stay. Will go for a 3rd
Top guest favorite
A serene outdoor area features a rectangular pool surrounded by a safety fence. A covered patio offers shaded seating, while a turquoise umbrella stands over a cushioned lounge chair. Lush greenery and landscaped gardens enhance the outdoor setting, contributing to a relaxed atmosphere.
Home in Apopka
4.99 out of 5 average rating, 105 reviews

Rate Discount~ Pool~Private Country Retreat

JillRating, 5 stars2 weeks ago
In town for a baseball tournament. Location to the fields was great — less than a 10 minute drive! Everything was clean. We enjoyed the pool after a hot day at the field. We appreciated the grill and used it to make some hamburgers and hot dogs. Kitchen was well equipped. Would definitely stay again if we need to be in the area.
Guest favorite
A tranquil pool area is surrounded by lush tropical plants, featuring a well-maintained saltwater pool with clear blue water. A shaded lounge area includes a comfortable chair, while a towel and snacks are neatly arranged beside the pool, highlighting a serene outdoor retreat.
Home in Orlando
4.9 out of 5 average rating, 146 reviews

Modern Tropical House Heated Salt Pool

LuisRating, 5 stars3 months ago
I had a wonderful stay at this property. The host provided clear and concise instructions, making the check-in process seamless. The house itself is beautiful, offering a perfect balance of privacy and comfort. Renting the entire place gave us the space we needed, and it came equipped with all the essentials. Highly recommend for anyone looking for a relaxing and practical getaway!
Guest favorite
A spacious backyard features a glistening pool surrounded by a neatly paved area. Metal dining chairs and a table are positioned near the pool. The house is visible in the background, showcasing a sleek design and multiple windows.
Home in Orlando
4.93 out of 5 average rating, 182 reviews

The Orlando Retreat.

TaylirRating, 5 stars3 weeks ago
Had a wonderful time!! Pool was great and house was very comfortable! We always feel right at home this is our second stay!! 😁
Guest favorite
The screened-in pool area features two green lounge chairs positioned beside a tranquil swimming pool. A spacious backyard is visible through the screen, showcasing lush greenery and a scenic sunrise casting soft colors across the sky.
Home in DeBary
4.88 out of 5 average rating, 102 reviews

Pool Home with Tiki Pub Close to Everything!

ChristianRating, 5 stars1 month ago
Amazing stay, and the homeowners were very helpful and understanding. Definitely look forward in staying again in the future.

Condo rentals with a pool

Guest favorite
An aerial view showcases the expansive pool area surrounded by lush landscaping. A large swimming pool is centrally positioned, flanked by a children's pool and numerous lounge chairs. The grounds feature walking paths and palm trees, contributing to the overall inviting atmosphere.
Condo in Orlando
4.92 out of 5 average rating, 101 reviews

Location,Location 3bd 2bth near parks conv.ct/Int.

LucindaRating, 5 stars1 week ago
Working with Isabela, was easy. The place was perfect for our needs. Beautiful, easy access to local attractions. Would highly recommend.
Guest favorite
The outdoor pool area features clear blue water surrounded by a deck. White lounge chairs are positioned around the pool, with a fence in the background. Lush green trees and shrubbery add a natural element to the space, complemented by a bright blue sky.
Condo in Kissimmee
4.87 out of 5 average rating, 134 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

KassidyRating, 5 stars1 week ago
The place was great! it was perfect for a quick family trip to Disney. Would highly recommend!
Guest favorite
A well-lit pool area is featured, showcasing a curved swimming pool with clear blue water. Surrounding amenities include several lounge chairs and palm trees. The building in the background contains multiple balconies, reflecting warm light from the interior.
Condo in Florida Center
4.88 out of 5 average rating, 225 reviews

Maria Luz Studio-Huge Terrace/Universal area.

LisaRating, 5 stars2 weeks ago
Fantastic and Wonderful! This place has by far been the best!
Guest favorite
The living area features a spacious gray sectional sofa accompanied by a bright blue chair. A modern wooden TV stand holds a flat-screen television. Natural light filters through large windows adorned with light curtains, complementing the neutral color palette.
Condo in Orlando
4.94 out of 5 average rating, 148 reviews

VCR2-108 Deluxe New Apartment - Convention Center

GuoRating, 5 stars1 week ago
We like this apartment very much. it's new and clean, location is also good, whole environment is good. The host reply very fast. will book it again when next time come. only not convenient is that can't stock luggage before check in and after check out.
Guest favorite
The modern living area features a spacious gray sectional sofa accented by colorful cushions. A minimalist coffee table is positioned centrally, and large sliding glass doors provide a view of the outdoor space, allowing natural light to fill the room. Light-colored cabinetry and appliances are visible in the kitchen area.
Condo in Kissimmee
4.93 out of 5 average rating, 196 reviews

3150-303 Resort Pool View Disney Universal Orlando

TrinityRating, 5 stars1 week ago
The place was clean and the host had excellent communication.
Top guest favorite
The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.
Condo in Orlando
5 out of 5 average rating, 142 reviews

Disney & Epic Free Shuttle, Kitchen

AlizahRating, 5 stars1 week ago
Great area to stay and awesome host!
Superhost
An outdoor pool area features palm trees and comfortable seating arrangements. Lounge chairs and shaded tables are positioned around the pool, which is surrounded by modern apartment buildings. A warm-toned lounge area offers additional seating, creating a welcoming space for relaxation.
Condo in Florida Center
4.78 out of 5 average rating, 110 reviews

LUXURY ONE BEDROOM CONDO NEAR UNIVERSAL

ShavornRating, 5 stars1 week ago
Great stay - very close to Universal and nearby attractions. Fast communication and the pool was a plus. Thank you!
Superhost
Condo in Davenport
4.84 out of 5 average rating, 170 reviews

Full-Service Gated Resort, Disney, Universal, MCO!

AngelRating, 5 stars1 week ago
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend

Home rentals with a private pool

A themed bedroom featuring a spacious bed with white bedding, set against a vivid space-themed mural. Two modern nightstands are flanked by unique lamps, and a large window allows natural light to illuminate the room while offering a view of the outdoors.
Villa in Four Corners
4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.
Superhost
An open-concept kitchen and dining area features a large island with seating for four, illuminated by pendant lights. Light-colored cabinetry and modern appliances complement the clean design. Arched doorways lead to the entrance, where natural light brightens the space from the large front door.
Home in Haines City
4.78 out of 5 average rating, 9 reviews

Minniehaha Castle Retreat

AnetteRating, 5 stars2 months ago
This house was ideal for our weekend. Everything we needed was provided, and the extras pillows, towels, and toiletries were a nice touch. The pool water heater was a great addition, making the water perfect for the time of year ($10 a day was worth it) . We enjoyed our stay and would recommend it to others.
Superhost
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.
Villa in Kissimmee
4.79 out of 5 average rating, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars1 month ago
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!
Guest favorite
Villa in Kissimmee
4.92 out of 5 average rating, 50 reviews

Family Retreat Near Disney with Pool & Hot Tub!

JenniferRating, 5 stars1 week ago
This home is just at pictured. Has everything you’ll need. Grill and propane being available on site were a very nice bonus. Hot tub and heated pool were fantastic after walking all day. Host was amazing and communication was very quick. Highly recommend this place and location
A spacious living area features an L-shaped sectional sofa facing a wall-mounted television. Large sliding doors allow light to fill the space, with views of the pool outside. A dining table with stylish chairs complements the modern decor, and warm tones enhance the inviting ambiance.
Home in Davenport
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars2 weeks ago
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.
A welcoming entrance sign for Solterra Resort is displayed with vibrant mosaic lettering. Surrounding greenery, including tall trees, complements the bright blue sky, creating an inviting first impression of the community.
Villa in Davenport
4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

CraigRating, 5 stars48 months ago
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.
A single-story yellow house is showcased, featuring a welcoming entrance and a well-manicured lawn with colorful landscaping. The driveway is paved with bricks, leading to a three-car garage. Lush trees and greenery frame the property, contributing to its tranquil environment.
Home in Kissimmee

Private Oasis with Pool & Spa- 3400clr

TarahRating, 5 stars1 week ago
The home was beautiful & exactly as described.

Quick stats about vacation rentals with a pool in Winter Springs

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$4,184 GYD before taxes and fees

  • Total number of reviews

    990 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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