
House holiday rentals in Winter Springs
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Springs
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Winter Springs
House rentals with a pool

3 bedroom Villa in Kissimmee
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.

Quiet Place, convenient to everything!
The home is as described. Nice and Clean. Quiet neighborhood. Highly Recommend!!!!

Private pool home near Downtown
Great house. Great host. Always attentive and responsive. 2nd stay. Will go for a 3rd

Bonheur Ala Maison
Leah was a great host and very responsive. The house was great for me and my family while traveling for work. Awesome location in great neighborhood. I felt safe for my family while at work during the day. The pool area was great and the accommodations were suitable for our family. My 3 children had a blast and they had enough room to space out when necessary. Thanks Leah again for our stay and being a great host.

Rate Discount~ Pool~Private Country Retreat
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.

Modern Tropical House Heated Salt Pool
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!

The Orlando Retreat.
Had a wonderful time!! Pool was great and house was very comfortable! We always feel right at home this is our second stay!! 😁

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!
Weekly house rentals

Beautiful House Completely Remodeled
We loved our stay. The house was clean and comfortable, and located in a super convenient location. We'll definitely come back the next time we come to Orlando!

Winter Park Guest Suite near UCF/FullSail/Rollins!
Grear stay!!! We were extremely surprised when we walked in the door. It was exactly as the photographs. The airbnb was very clean. We did encounter a few flies in the airbnb but my son was able to get rid of them. I texted the hosts and they responded right away. They were apologetic and assured me that it had never happened before and would look into it. The very next day, they sent someone to try to figure out the problem. I believe it was because the garbage bin was next to the airbnb. Once it was moved over to the other side, we did not experience anymore flies. The airbnb was closed to Full Sail University, where my son did a one week summer program. It was also very close to grocery stores and restaurants. I was able to buy groceries and at times get them delivered. I was able to cook in there two range burner which was my number one reason for staying at an airbnb instead of a hotel. The airb had the pots, pans, and dishes. I did not rent a car and the Uber service was great.

Moxy Luxe Vacation / Heated Pool/ King Bed Ste
Enjoyed our stay. Home was just as pictures advertised. Really quiet and peaceful neighborhood. I recommend this place.

House of Blues-3 Bedrooms+GameRoom
I was only there for one night but it was great and exactly what I needed at the time. The house was clean and the beds were comfortable. I will stay there again if in the area.

New built Private Studio Orlando/Winter Park area
This sweet little suite met all my needs for a week visiting friends. There was an internet problem one day, but Diana stayed in communication with me and the malfunction was corrected in a timely manner. The place is clean and well-appointed. I highly recommend it, and I would definitely return.

Blue Villa | 8 PPL | Heated Pool | BBQ | Top Area
The Blue Villa was an absolutely wonderful accommodation! From check in to check out, there was easy access, immediate responses to communications, peaceful neighborhood, great restaurants near by, leading to a fantastic stay. We would definitely return!

May Discounts! Close to Disney & Universal Parks!
Everything was perfectly fine, only upon entry the floors definitely were not swept well or mopped. As far as just that the stay was great. Video games were a treat for us, got to jam out on guitar hero and enjoy my time there. Definitely recommend the stay !

Spacious 4 bedroom single story home
Ronald's place was paradise!! Beautiful house on beautifully maintained property, in a quiet neighborhood. It doesn't get better than that! The house was so spacious and the backyard was perfect for my kids to play and watch animals from. Neighborhood was perfect for evening and morning walks. The house was well stocked with lots of towels, linens, and kitchen supplies. It was an awesome long-term stay and I highly recommend it!
Private house rentals

SEEN ON TV! Private Resort, Nintendo-theme Game Rm
Caitlin was incredibly responsive whenever we had a question about anything. The house was incredible, they took so much time and money making all the amenities and details first class. Everything was explained in easy to read pamphlets that described everything. The game room was a big hit, and of course the bbq and pool area, and my family absolutely loved it. Everyone was raving at how nice a place the house was. I highly recommend staying here if you can, I would definitely rent again if we’re ever back in the area.

Relaxing 2 bedroom house
Beautiful and comfortable home with everything you need! Comfortable beds and great location! Thank you!

Joe's Bar and Grill
Second time at Joe’s. Among the best AirBnB’s in our extensive experience! Stocked with every little thing you might want (ie: instant read thermometer for grilling). Joe reached out to help before I even had a chance to ask about the WiFi (wife had unplugged router by accident) and opened the garage door when my kids locked themselves out. House is private and quiet and the pool area is awesome. Lot of activities within easy reach. Such an easy, comfortable stay. Thanks again Joe and crew!

Lakefront Paradise Near Attractions
What a lovely home this is. Very thoughtfully done and beautiful setting. Our contact person Gabriel was very very responsive. There were three couples staying here together and there was plenty of room to enjoy visiting or alone time.

Luxurious and modern cottage near UCF
We loved Alejandro’s property. It was well-supplied, clean, and private. We loved having a large screened in porch to eat breakfast in the morning and relax in the evenings. When we let Alejandro know about a potential issue, he had someone come take care of it quickly. We will definitely reserve this spot again.

The Winter Park Experience
The host was incredible and attentive to every detail. From start to finish the experience was seamless. The host was responsive and accommodating and made sure we felt like home when we were staying there. The host went above and beyond for us. There are not enough good words for me to say about the host, we highly recommend staying here. 12/10 experience

Y2K Home in Orlando 2 min to UCF
Great peaceful stay. Very clean and host communicates with me throughout the stay .Definitely recommend

Orlando Poolside Oasis
My friends and I really enjoyed the house it was very clean, well-organized, and overall a great place to stay. We didn’t encounter any issues, except for the lack of lighting in the backyard at night, which made it difficult to use the pool after dark. It wasn’t a major problem, but having some outdoor lights would definitely be a nice addition. Other than that, everything was perfect! The owners were very helpful and even allowed us early check-in, which we truly appreciated.
Quick stats about house rentals in Winter Springs
Total rentals
50 properties
Nightly prices starting at
₹1,727 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Central Florida Holiday rentals
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Rentals with a patio Winter Springs
- Rentals with outdoor seating Winter Springs
- Apartment rentals Winter Springs
- Family-friendly rentals Winter Springs
- Rentals with a washing machine and dryer Winter Springs
- Rentals with pools Winter Springs
- Pet-friendly rentals Winter Springs
- House rentals Seminole County
- House rentals Florida
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- Playalinda Beach
- ESPN Wide World of Sports
- Titusville Beach
- Amway Center
- Epcot
- Daytona International Speedway
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park