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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, 307 reviews

King Bed | Grill | Pets | Central Location!

LaurenRating, 5 stars2 weeks ago
we came to town for one evening for a concert at camping world stadium. The house, with traffic on the way, was 20 minutes from the stadium which was very convenient for us. because we only got to stay for one night we didn't get to enjoy the house to it's full potential but our impression was great! everything was very clean and beds were comfortable. Pool was awesome! The only thing that initially concerned us was it seemed like the surrounding neighborhood was a little sketchy. We had 0 issues with safety but it was just our initial impression. We will book again if going to the area!
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.
Guest favorite
Home in Casselberry
4.87 out of 5 average rating, 101 reviews

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

BeverlyRating, 5 stars1 week ago
Very nice inside and spacious backyards closed in games for the children and family to do lots of beds I like that you can shut the master door and everybody can still get to the bathroom as a huge thing for me.
Superhost
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, 259 reviews

Gated community XL pool Home 2500sq/f

JackieRating, 5 stars2 weeks ago
Heidy’s house was wonderful! Very clean and well stocked. The pool and backyard were very peaceful, we spent a lot of our time out on the patio. The master king bed was super comfortable! Heidy left us some cold water in the fridge which was needed upon arrival, June is very hot in Florida! Would 100 percent recommend!
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!
Guest favorite
A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.
Home in Orlando
4.88 out of 5 average rating, 203 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

WadeRating, 5 stars4 days ago
The place was amazing! The private pool and hot tub were exactly what we needed during a week of visiting theme parks. The backyard is so relaxing. Shopping and dining is very close as are the Universal parks and the airport. You can't beat the location! Would definitely stay here again! Thanks for a great stay!
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.
Top guest favorite
The exterior of the home showcases a modern façade with a manicured lawn and a two-car garage. Inside, a spacious living area is furnished with a comfortable sofa and a large TV displaying a streaming service. A bright bedroom features a queen bed against light-colored walls, with natural light illuminating the space. The outdoor pool area is enclosed by a screened patio, highlighting the inviting water and surrounding lounge chairs.
Home in Kissimmee
4.99 out of 5 average rating, 106 reviews

Traveler's Dream - King Bed, Pool, Games, Disney+

LaverneRating, 5 stars3 days ago
We really enjoyed our stay. It was comfortable, clean, and had everything we needed. Thank you for being such a great host—we’d love to come back in the future!

Weekly house rentals

Guest favorite
An open living area features a modern kitchen equipped with stainless steel appliances, including a microwave and refrigerator. A comfortable green sofa with throw pillows faces a wall-mounted television. A glass coffee table is surrounded by four chairs, enhancing the inviting communal space.
Home in Winter Park
4.93 out of 5 average rating, 72 reviews

Winter Park Guest Suite near UCF/FullSail/Rollins!

PaulinaRating, 5 stars1 week ago
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.
Top guest favorite
A private outdoor area features a sparkling pool alongside a spa, both surrounded by a spacious tiled terrace. The exterior showcases modern architectural details, with a spiral staircase leading to an upper level. Large glass doors provide an open view into the home's living spaces.
Home in Baldwin Park
5 out of 5 average rating, 53 reviews

SEEN ON TV! Private Resort, Nintendo-theme Game Rm

RichardRating, 5 stars3 weeks ago
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.
Guest favorite
The kitchen features white cabinetry and a large island with two cushioned stools. Stainless steel appliances, including a refrigerator and oven, are included. Natural light is provided by multiple windows, enhancing the bright and functional space.
Home in Winter Park
4.85 out of 5 average rating, 55 reviews

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!

JohnRating, 5 stars5 days ago
This one you’ll find everything that he says is true great guy great place
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 stars3 weeks ago
Great location, very nice house
Guest favorite
A modern kitchen features white cabinetry and granite countertops, complemented by stainless steel appliances. Bright, natural light streams through the windows, illuminating the open layout. Pendant lights hang above the central island, while a dining area is visible in the background.
Home in Orlando
4.98 out of 5 average rating, 45 reviews

Charming Bungalow in Winter Park

TaralynnRating, 5 stars1 week ago
Loved the stay at this place! The instructions were clear on how to get to the parking and the large kitchen island was a great gathering spot. This house had more than enough space for what our needs were. Host was very responsive. Thank you for having us!
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, 41 reviews

The Winter Park Experience

MarieRating, 5 stars1 week 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, 24 reviews

King/Queen Quiet Vibey Bungalow

ClaudiaRating, 5 stars1 day ago
Chris’ place was simply beautiful! Comfortable, clean, all equipped! We really enjoyed the place and surroundings. Chris was very attentive at helping us get a high chair for my little one. Definitely will come back!

Private 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
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.
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!
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!
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
A serene bedroom features a spacious bed dressed in crisp white linens, flanked by modern bedside lamps. A vibrant floral accent wall adds a pop of color, while light filters through plantation shutters, creating a calming atmosphere.
Home in College Park
4.96 out of 5 average rating, 93 reviews

Yale House in College Park 2 mi from Downtown

AspenRating, 5 stars2 weeks ago
Cute house with character- great place to stay! Loved that there was a grocery store within walking distance!
Guest favorite
A spacious living area is presented with a large sectional sofa and a stylish coffee table at the center. A modern ceiling fan circulates air, while a mounted television above a charming fireplace enhances the space. Natural light enters through nearby doorways.
Home in Orlando
4.93 out of 5 average rating, 15 reviews

Downtown Dream Spot - Trendy, Upscale, & Modern

SocorroRating, 5 stars4 days ago
Great place, stay was amazing and felt right at home, shower was a bit cold but nothing we couldn’t get used to especially with the hot weather.

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

Destinations to explore

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