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House vacation rentals in Winter Park

Find and book unique houses on Airbnb

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Popular amenities for Winter Park house rentals

House rentals with a pool

Superhost
An open-concept living area features a sleek black sectional sofa paired with a matching chaise. A coffee table sits center stage, adorned with a potted orchid. A wall-mounted TV displays vibrant images, while a piece of artwork adds a modern touch to the decor.
Home in Orlando
4.84 out of 5 average rating, 306 reviews

King Bed | Grill | Pets | Central Location!

SianoahRating, 5 stars3 weeks ago
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.
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.
Top guest favorite
A sparkling pool is surrounded by a screened enclosure, featuring a yellow floating toy. A soothing spa area with bubbling jets is visible, with lush greenery framing the scene. A shaded area with an umbrella is included, providing a relaxing retreat.
Home in Minneola
4.98 out of 5 average rating, 130 reviews

Pool + Heated spa Family friendly King suite Oasis

VivianRating, 5 stars1 week ago
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!!! 💕
Guest favorite
A bright pink inflatable flamingo floats on the surface of a clear pool, surrounded by tropical plants and a screened enclosure. Sunlight reflects off the water, creating a relaxing atmosphere for outdoor leisure.
Home in Oviedo
4.92 out of 5 average rating, 335 reviews

4 bedroom Modern pool home, close to UCF&Boombah

VictoriaRating, 5 stars3 weeks ago
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!
Top guest favorite
The private pool is surrounded by lush greenery and features a gentle waterfall cascading into the water. Colorful plants line the edge, offering a tranquil environment for relaxation. The clear blue water is inviting and complements the serene outdoor setting.
Home in Ocoee
4.96 out of 5 average rating, 110 reviews

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

BillRating, 5 stars1 week ago
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.
Superhost
A spacious pool area features a crystal-clear pool surrounded by lounge chairs and umbrellas. Lush palm trees provide shade, and a small fence enhances privacy. A gentle slope leads to a shallow section with jets, blending seamlessly into the inviting water.
Home in Orlando
4.86 out of 5 average rating, 195 reviews

Year around Heated Pool 7 min from Airport!

JoseRating, 5 stars1 week ago
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.
Guest favorite
Home in Lake Mary
4.88 out of 5 average rating, 99 reviews

Markham Woods 4BR Pool Retreat near Attractions

LeslieRating, 5 stars2 weeks ago
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.
Guest favorite
A private outdoor space features a sparkling pool with a waterfall and spillover spa. Sun loungers are positioned around the pool deck made of beige pavers. Lush greenery and palm trees create a serene backdrop under a partly cloudy sky.
Home in Four Corners
4.96 out of 5 average rating, 178 reviews

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

KaylaRating, 5 stars3 weeks ago
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

Superhost
A serene outdoor area features a sparkling pool surrounded by a paved patio. Two gazebos provide shaded seating options, complemented by a few lounge chairs and decorative planters. The fenced yard offers privacy, and the space invites relaxation and gatherings.
Home in Winter Park
5 out of 5 average rating, 7 reviews

Casa Winter Park

CristinaRating, 5 stars2 weeks ago
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!
Superhost
A light-filled living area features a modern cream-colored sofa accented with orange pillows. A dark coffee table sits in front, complemented by two table lamps. Wall art displays floral designs, and a mirror reflects the space, enhancing the open feel. A doorway leads to additional areas.
Home in Winter Park
4.83 out of 5 average rating, 70 reviews

3 BR minutes walk to Park Avenue

MichaelRating, 5 stars3 weeks ago
Solid place with great proximity to restaurants.
Guest favorite
An open living area features modern furnishings, including a dark leather sectional and two accent chairs. The space is complemented by a wooden coffee table and clear views into the kitchen, which showcases sleek cabinets and stainless steel appliances. A staircase leads to the upper level.
Home in Orlando
5 out of 5 average rating, 10 reviews

Spacious Lakefront 2 Bed Home-Close to Everything!

MichaelaRating, 5 stars2 weeks ago
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!
Superhost
A spacious bedroom features a comfortable bed with a textured blue throw and an array of decorative pillows. Two bedside lamps provide soft lighting beside the bed. Framed pictures adorn the wall above, while a large closet with double doors is visible in the background.
Home in Baldwin Park
4.72 out of 5 average rating, 39 reviews

Walk To Bike Trail, Baldwin Lake

CynthiaRating, 5 stars5 months ago
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.
Top guest favorite
A bright living area features comfortable gray sofas positioned around a glass coffee table. Natural light enters through a nearby window, illuminating the space. A flat-screen television is mounted on the wall, and a decorative clock adds a stylish touch.
Home in Winter Park
5 out of 5 average rating, 40 reviews

The Winter Park Experience

MarieRating, 5 stars6 days ago
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
Top guest favorite
A comfortable living area features a warm orange sofa paired with a matching accent chair. A round coffee table sits on a colorful area rug. Large windows provide ample natural light, and artwork adorns the walls. A dining space is visible in the background.
Home in Orlando
5 out of 5 average rating, 23 reviews

King/Queen Quiet Vibey Bungalow

LydiaRating, 5 stars1 week ago
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.
Superhost
A well-lit living area features hardwood flooring and an archway leading to another space. A flat-screen television is positioned on a wooden media console. Comfortable seating includes a gray sofa and an accent chair, with a central coffee table adding functionality.
Home in Winter Park
5 out of 5 average rating, 6 reviews

Cheerful 4-Bedroom Home With Pool

AmandaRating, 5 stars1 week ago
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!
Top guest favorite
A cozy outdoor fire pit area is surrounded by four chairs and a circular stone border. Soft lighting from string lights creates a welcoming ambiance in the fenced backyard, with a well-maintained grassy area and a pathway leading to the bungalow in the background.
Home in Orlando
4.94 out of 5 average rating, 85 reviews

Colonialtown Bungalow

MichaelRating, 5 stars2 weeks ago
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

Guest favorite
The exterior view of the bungalow features a landscaped front yard with well-maintained greenery. A welcoming entrance with a bright red door is highlighted, complemented by vibrant hedge plants. The driveway leads to an attached one-car garage, set against a backdrop of mature trees.
Home in Winter Park
4.88 out of 5 average rating, 26 reviews

Winter Park - Cozy retreat near Lake Killarney

LeeRating, 5 stars1 week ago
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
Guest favorite
An outdoor space features a large pool surrounded by a patio area. Comfortable seating and an umbrella are positioned under a shaded area. Lush greenery lines the back and sides, providing privacy, while the main house showcases a welcoming design with large doors leading out to the pool.
Home in Winter Park
4.88 out of 5 average rating, 89 reviews

Charming Retreat In Winter Park

AlanRating, 5 stars2 weeks ago
Great location, very nice house
Guest favorite
A living room area features a comfortable seating arrangement with a sectional sofa and armchair. A television is positioned on a glass-top stand, accompanied by decorative lamps. A mirror reflects light, enhancing the space, while a window with blinds allows natural light to filter in.
Home in Baldwin Park
4.93 out of 5 average rating, 80 reviews

City Charmer

SoniaRating, 5 stars3 weeks ago
This place was amazing. It had everything we needed plus more. Patrick is a very good host. Felt right at home.
Superhost
A private pool is framed by a spacious yard, featuring comfortable lounge seating and floating pool toys. Outdoor lighting creates a warm atmosphere as dusk settles, and nearby hammocks offer spots for relaxation. The home has multiple windows that provide clear access to the outdoor space.
Home in Winter Park
4.71 out of 5 average rating, 14 reviews

Citrus Oasis: 4BR Pool Home

NicholasRating, 5 stars3 weeks ago
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.
Guest favorite
A modern single-story house is set on a spacious lot, where greenery frames the exterior. The driveway leads up to a two-car garage, and large windows offer a view of the interior. A well-maintained lawn complements the inviting façade.
Home in Winter Park
5 out of 5 average rating, 25 reviews

Newly Renovated 2 Bed/2Bath, Fully Furnished Home

IreneRating, 5 stars3 weeks ago
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!
Guest favorite
A spacious living area showcases comfortable seating with colorful chairs in blue and orange. An elegant coffee table occupies the center, while a large TV hangs on the wall. Bright lighting enhances the open floor plan, accented by decorative plants and modern artwork.
Home in Casselberry
4.92 out of 5 average rating, 26 reviews

Blue Villa | 8 PPL | Heated Pool | BBQ | Top Area

SabrinaRating, 5 stars1 day ago
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!
Top guest favorite
A spacious living area features a comfortable gray sectional sofa facing a large flat-screen TV mounted on a white wall. Light hardwood floors complement the contemporary decor, which includes a wooden dining table, decorative plants, and expansive glass doors leading to an outdoor space.
Home in Orlando
4.98 out of 5 average rating, 53 reviews

Stunning Modern 2/2 Home in Hip Enclave near DT

CarolRating, 5 stars1 month ago
Beautifully remodeled home in popular area. Bathrooms, kitchen and common areas exquisite. Host is very accommodating and responsive.
Top guest favorite
The exterior of the bungalow is surrounded by vibrant greenery, featuring classic window shutters and inviting textures. Elements indicating various amenities include icons for bicycle rentals, pet policy, kitchen accessibility, rental vehicles, and event approvals, enhancing the overall experience.
Home in College Park
5 out of 5 average rating, 12 reviews

3BR Oasis DT ORL, Full Kitchen & Fenced Yard!

DomineRating, 5 stars1 week ago
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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