House vacation rentals in Winter Springs

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Popular amenities for Winter Springs house rentals

House rentals with a pool

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
Guest favorite
A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.
Home in Maitland
4.86 out of 5 average rating, 123 reviews

Bonheur Ala Maison

RyanRating, 5 stars1 week ago
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.
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
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

Top guest favorite
A spacious living area is displayed, featuring a sectional sofa and a large wall-mounted TV. The open kitchen showcases modern appliances and a dining table for six. Natural light floods the space through sliding glass doors that lead to the backyard.
Home in Orlando
4.96 out of 5 average rating, 130 reviews

Beautiful House Completely Remodeled

AnnaRating, 5 stars4 days ago
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!
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 stars6 days 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.
Guest favorite
An open living area showcases a modern black sofa facing a large flat-screen TV mounted on the wall. A coffee table holds board games, while a ceiling fan and decorative lighting enhance the space. The adjoining dining area and kitchen are visible in the background.
Home in Casselberry
4.89 out of 5 average rating, 63 reviews

Moxy Luxe Vacation / Heated Pool/ King Bed Ste

NelsonRating, 5 stars1 week ago
Enjoyed our stay. Home was just as pictures advertised. Really quiet and peaceful neighborhood. I recommend this place.
Guest favorite
A spacious dining area is furnished with a large table surrounded by six chairs, each featuring a vibrant floral pattern. A chandelier hangs above the table, illuminating the space. Sliding glass doors provide access to the outdoor area, allowing natural light to fill the room.
Home in Casselberry
4.81 out of 5 average rating, 37 reviews

House of Blues-3 Bedrooms+GameRoom

JesusRating, 5 stars2 weeks ago
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.
Guest favorite
The entrance area is shown, featuring a welcoming front door framed by two lantern-style lights. A pumpkin sits on the ground next to a small garden bed with plants. A mat lies in front of the door, creating a cozy entryway.
Home in Winter Park
4.95 out of 5 average rating, 20 reviews

New built Private Studio Orlando/Winter Park area

GregoryRating, 5 stars1 month ago
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.
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!
Guest favorite
A spacious backyard features well-maintained grass, surrounded by trees. A seating area includes a table and chairs, while a fire pit adds an inviting element. Adjacent structures provide additional storage, and the updated home can be glimpsed in the background, enhancing the outdoor experience.
Home in Casselberry
4.93 out of 5 average rating, 40 reviews

May Discounts! Close to Disney & Universal Parks!

BrandonRating, 5 stars1 week ago
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 !
Guest favorite
A spacious living room is highlighted by large windows allowing natural light. A brick fireplace serves as a central feature, complemented by a comfortable sectional sofa and armchairs. A coffee table sits on a textured rug, creating an inviting space for relaxation.
Home in Winter Springs
5 out of 5 average rating, 8 reviews

Spacious 4 bedroom single story home

MarcyRating, 5 stars2 weeks ago
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

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
A light-filled living area features a tufted gray sofa adorned with decorative pillows. A wooden coffee table is centered on a patterned area rug, with a small decorative bowl placed on top. Natural light filters through multiple window blinds, illuminating the warm hardwood floor.
Home in Sanford
4.88 out of 5 average rating, 41 reviews

Relaxing 2 bedroom house

DenisseRating, 5 stars3 days ago
Beautiful and comfortable home with everything you need! Comfortable beds and great location! Thank you!
Top guest favorite
The image displays the logo for Joe's Bar & Grill, featuring stylized text in vibrant colors. Flanking the logo are palm trees on either side, with a graphic of a swimming pool in the center, enhancing the tropical theme. Various playful tropical elements are integrated into the design.
Home in Altamonte Springs
5 out of 5 average rating, 55 reviews

Joe's Bar and Grill

RyanRating, 5 stars3 weeks ago
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!
Guest favorite
A serene sunset paints the sky in hues of orange and pink, visible through the silhouettes of tall cypress trees. The calm waters of Lake Killarney reflect the vibrant colors, creating a peaceful ambiance along the landscaped lawn and tiled walkway.
Home in Winter Park
4.92 out of 5 average rating, 53 reviews

Lakefront Paradise Near Attractions

CathyRating, 5 stars1 month ago
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.
Guest favorite
The living area features a modern sectional sofa arranged around a textured coffee table. A colorful area rug adds warmth. A dining table with black chairs is set nearby, illuminated by pendant lights. Large windows provide ample natural light, and contemporary wall art enhances the ambiance.
Home in Orlando
4.94 out of 5 average rating, 94 reviews

Luxurious and modern cottage near UCF

StacyRating, 5 stars2 days ago
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.
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
Superhost
A vibrant bedroom features purple walls and artistic decor. A spacious bed is dressed in a black-and-white checkered blanket, complemented by colorful pillows. A window allows natural light to illuminate the room, highlighting green plants nearby. A sitting area includes a black couch, enhancing comfort.
Home in Orlando
4.73 out of 5 average rating, 26 reviews

Y2K Home in Orlando 2 min to UCF

DeziahRating, 5 stars1 day ago
Great peaceful stay. Very clean and host communicates with me throughout the stay .Definitely recommend
Guest favorite
The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.
Home in Altamonte Springs
4.95 out of 5 average rating, 86 reviews

Orlando Poolside Oasis

DarielRating, 5 stars3 weeks ago
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

    G$4,184 GYD 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