
House vacation rentals in Winter Park
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Top-rated house rentals in Winter Park
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Vacation rentals for every style
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Popular amenities for Winter Park house rentals
House rentals with a pool

King Bed | Grill | Pets | Central Location!
This Airbnb is definitely one we will keep in rotation. With an elderly in-law, we needed a place with a fourth bedroom. The bonus was the pool and we took full advantage of that just to relax and enjoy. Everything we needed was close by and easy to get to. All in all the hosts home felt like home. We hope to stay again in the future.

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.

Pool + Heated spa Family friendly King suite Oasis
What an amazing 2 weeks with family!! Don’t hesitate to book this GEM of a home! It’s beautiful, peaceful (on a culdesac) SUPER QUIET at night, great spots to eat at the waterfront and all around Minneola in general. We had an issue with warming the spa and both were very responsive, ordered the part and within 2 days its was perfect. This house had EVERY amenity you would need and then some…games indoor and outdoor, kids books, fire pit, swing, blankets to cozy up on couch, dog bowls, leashes, toys etc. They truly make you feel like it’s home. We can’t rave about it enough!! We were only a short half hour drive away from Disney also. Our 2 small dogs absolutely LOVED chasing lizards and frogs around the pool area! We would LOVE to come back if they would have us! Thank you again for being such great hosts! All you do to make your guests feel comfortable at home does NOT go unnoticed! Until next time beautiful Clermont/Minneola!!! 💕

4 bedroom Modern pool home, close to UCF&Boombah
Loida was an amazing person to speak with. Resolved any and all issues promptly and with great grace. I would definitely stay here again if and when I am in the area again!

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.

Year around Heated Pool 7 min from Airport!
Super nice, pictures do not do it justice. Upgrades clearly done little by little. Pool is amazing, outdoor area great, cozy yet spacious. Would book here again and again. 20 min from Camping World Stadium, 15 min from Downtown Orlando truly accurate, easy in and out from main road and highways.

Markham Woods 4BR Pool Retreat near Attractions
Ahmad was an absolute wonderful host. After arriving a little early to town I asked about an early check in and he quickly responded to let me know I could go ahead and check in. The house is absolutely beautiful, peaceful and spotless. I very much appreciated all the little details and extra amenities. The washer and dryer works wonderful. The beds were clean and comfy, the showers were great. I loved all the storage space for our belongs as well. The location was great as well, literally within miles of anything you could need. The pool was also really nice and my kids very much enjoyed it. I will say they did get little scrapes on the bottom of their feet from the floor of the pool but that’s not a huge deal. So I would suggest water shoes inside the pool. All in all If I could give Ahmad 10 stars I would! I will definitely book this place again. By far my most favorite place I have ever booked so far.

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

Casa Winter Park
This was a spacious and hospitable place. Juan was responsive and understanding. The house was sparkling clean and very beautiful and comfortable. I didn't do any cooking but this was an extremely well-appointed kitchen. Pool is lovely. We loved our stay here!

3 BR minutes walk to Park Avenue
Solid place with great proximity to restaurants.

Spacious Lakefront 2 Bed Home-Close to Everything!
Personally I was sad to leave! Such a lovely location and getting to enjoy the views from the kitchen island or hanging out on the dock every day was so peaceful. Just the kind of vacation I needed to get me through the rest of my year 🌴 Our host was very kind and responded very quickly! Book a stay here!

Walk To Bike Trail, Baldwin Lake
We had a very comfortable stay. Michelle’s has a charming place close to a lovely park where we took several walks. Also the restaurants in the area are very good.

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

King/Queen Quiet Vibey Bungalow
The home was clean and comfortable. Plenty of Restaurants nearby, in walking distance. Chris was very responsive and friendly. I would definitely stay here again.

Cheerful 4-Bedroom Home With Pool
We had a great stay at this Winter Park apartment. It was spacious, comfortable, and very well located — close to everything we needed. The host was responsive, helpful, and accommodating throughout our stay, which made the experience even better. Would definitely recommend to anyone visiting the area!

Colonialtown Bungalow
Great place to stay when we came in to town for a concert. Short drive to many great places to eat and shop. House had a great cozy feel in a nice and quiet area. Family had a relaxing time. Host was very quick to respond and provided great instructions.
Private house rentals

Winter Park - Cozy retreat near Lake Killarney
This is a great house with a nice big backyard very private and comfortable. Really close to downtown Winter Park and close to the interstate. Great restaurants close by. Highly recommend

Charming Retreat In Winter Park
Great location, very nice house

City Charmer
This place was amazing. It had everything we needed plus more. Patrick is a very good host. Felt right at home.

Citrus Oasis: 4BR Pool Home
Great place in a great area. Jacob was quick to answer any questions and fix any minor bumps that might arise. Very satisfied and would love to come back again if I'm in the area.

Newly Renovated 2 Bed/2Bath, Fully Furnished Home
The location was difficult to find because of maps. Everything else was great. One of my guests said "it's a good Airbnb when there's real plants!" The location was private, nice office space, bright everything good!

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!

Stunning Modern 2/2 Home in Hip Enclave near DT
Beautifully remodeled home in popular area. Bathrooms, kitchen and common areas exquisite. Host is very accommodating and responsive.

3BR Oasis DT ORL, Full Kitchen & Fenced Yard!
Such a lovely and cute place! We will definitely be back if we are in Orlando again! The space was perfect for us and a calming retreat to come home to.❤️
Quick stats about house rentals in Winter Park
Total rentals
170 properties
Total number of reviews
5.1K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
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- 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
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