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House vacation rentals in Longwood

Find and book unique houses on Airbnb

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Popular amenities for Longwood house rentals

House rentals with a pool

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
5 out of 5 average rating, 126 reviews

Private pool home near Downtown

JessicaRating, 5 stars4 days ago
This is instantly become my favorite Airbnb. Such a wonderful and beautiful experience. It’s an absolutely fantastic location while also enjoying the aspect of privacy. This will definitely be my go to anytime that I have to come into Orlando!
Top guest favorite
Home in Davenport
4.91 out of 5 average rating, 126 reviews

The Shire -Private Pool & Hot Tub, Close to parks!

DanaRating, 5 stars2 weeks ago
Monica was very responsive when we had an issue with one of the bathrooms and got it promptly fixed! We have stayed at this house previously and love the location and amenities. We will be back!
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, 252 reviews

Gated community XL pool Home 2500sq/f

KatieRating, 5 stars3 weeks ago
Heidy and her husband Michael were absolutely wonderful hosts while we were visiting Lake Mary. We loved the Sanford area and all the recommendations Heidy gave us. Their home is beautiful, clean, cozy and the backyard is an absolute dream. Our girls loved the pool. It is “cannon ball approved” by my 10 yo. My husband accidentally left the garage door open when we left for Universal for the day, but Michael was notified and kindly went and closed it and checked on the house for us. We loved having them close by. They were so sweet and helpful. We had the best time on our vacation and can’t wait to visit 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, 200 reviews

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

JamieRating, 5 stars1 week ago
This home was clean and conveniently located near a ton of things to do, paces to eat, and a short drive to Disney.
Top guest favorite
A private, screened-in pool area is visible, featuring a clear blue pool and an attached hot tub. Several lounge chairs are arranged along the poolside, and a shaded umbrella stands nearby, providing a relaxing outdoor space.
Home in Clermont
4.92 out of 5 average rating, 144 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

TyreseRating, 5 stars3 months ago
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.
Guest favorite
A screened patio surrounds a refreshing pool, featuring a slide and a small swimming area. Several blue chairs surround a table, offering a space for outdoor dining. Lush trees provide a natural backdrop, enhancing the tranquil outdoor setting.
Home in Apopka
4.87 out of 5 average rating, 139 reviews

Country Pool home on 2 acres-30 minutes to Disney

LindaRating, 5 stars3 weeks ago
This was the perfect location for our family! The kids enjoyed the pool and swings. We enjoyed everything about the home. We would definitely book this home again.
Superhost
A spacious pool area is enclosed by a screened-in lanai, showcasing a clear pool with a white deck. Nearby, a seating area is positioned beside the pool, offering a serene view of the surrounding green space.
Home in Kissimmee
4.82 out of 5 average rating, 116 reviews

Pool House in Kissimmee

DouglasRating, 5 stars1 month ago
Everything was great. We came down to see our granddaughters on spring break. Usually don’t want to swim,this time they did. Wish I would have spent the money to heat the pool. They enjoyed playing pool and wanted to play air hockey but no puck but amazon took care of that. The master on one end and other bedrooms on the opposite end was a big plus for we got up earlier so we didn’t wake them. Would definitely recommend and would love to come back next year.
Superhost
An aerial view displays a single-story home surrounded by green lawns and trees. Neighboring properties feature screened-in pools. A clear driveway leads to the entrance, providing a sense of space and accessibility. The quiet neighborhood setting is evident in the layout.
Home in Davenport
4.81 out of 5 average rating, 180 reviews

4BR-2KingMasters-SpaHeat-Private Pool-Remodeled

LaylaRating, 5 stars1 week ago
Tetyana’s place was very clean, welcoming, and felt like home away from home. It was conveniently located near Disney and easy to access. The bed was very comfortable and I slept like a baby. The master bath was a great way to unwind and relax after walking over 10,000 steps at the Disney parks. We LOVED the jacuzzi/pool combo and how secluded it was. Very quiet neighborhood, responsive host, and easy check-in. We’ll be back. :)

Weekly house rentals

Top guest favorite
A cozy living room features an oversized L-shaped couch adorned with colorful cushions. A rustic coffee table sits in front, and a large television is mounted on the wall. Bright wall colors and a horse painting create a welcoming atmosphere, with natural light illuminating the space.
Home in Orlando
4.94 out of 5 average rating, 34 reviews

Pet-Friendly Bungalow Near Downtown Orlando

LisaRating, 5 stars6 days ago
Megan was really attentive and great to book with! The house felt very comfortable, like I was staying at a good friend’s house for a few days. I loved being so close to downtown and really appreciated the pet friendly hospitality as well!
Guest favorite
Home in Davenport
4.79 out of 5 average rating, 48 reviews

969T-Single Storey House 20 min from Disney 4 bed

AlciraRating, 5 stars2 days ago
Tatiana es una excelente profesional, amigable, está atenta a todos los.requerimientos. La casa es amplia, luminosa y con todo los detalles para pasar una estadía confortable y placentera Nada negativo para mencionar, todo lo contrario
Guest favorite
The living area features a light color scheme with a sectional sofa adorned with yellow and green cushions. A modern coffee table sits at the center, complementing the entertainment unit housing a flat-screen TV. Natural light enters through the front door, enhancing the space.
Home in Kissimmee
4.95 out of 5 average rating, 22 reviews

9001-WW 5 Bedroom ALL Suites Pool Home

AmberRating, 5 stars3 months ago
Found this air b&b last minute and late due to having to leaving our precious air b&b. Magic was very helpful and responsive on such short notice. I’m so thankful we found this place my kids absolutely loved it and they will remember it forever! It was very clean. They were also very accommodating. Had an issue with the dishwasher but it was quickly fixed. We absolutely loved it, thank you again!! You made our vacation amazing. Perfect house for our Disney Christmas surprise. We will be back.
Superhost
The exterior of the residence features a warm-toned facade with decorative arches. Lush landscaping, including palm trees and colorful foliage, enhances the welcoming appearance. A paved walkway leads to the entry, surrounded by meticulously maintained green grass.
Home in Kissimmee
4.9 out of 5 average rating, 123 reviews

5BD Windsor Westside Private Pool (WW 9025)

LydiaRating, 5 stars2 months ago
Jose is very friendly and respond most of the time within 15 minutes. Easy to talk to. We loved the place. We were already familiar with the subdivision and the area. We were with 6 and had plenty of rooms and bathrooms
Superhost
The outdoor area features a heated pool and a nearby jacuzzi, surrounded by a screened enclosure. A serene lake view is visible beyond the pool area, with reflections of the sky and clouds on the water's surface.
Home in Kissimmee
4.77 out of 5 average rating, 142 reviews

3/2 Family Home, climatized Pool and Sunset Views

MilagrosRating, 5 stars4 weeks ago
Our host Ana was very helpful and would always respond quickly to any questions I had. I had a great experience.
Guest favorite
A spacious living area features an expansive sectional sofa, complemented by a glass coffee table. The open kitchen, equipped with modern appliances and white cabinetry, is visible in the background. Elegant lighting fixtures enhance the contemporary design, creating a welcoming atmosphere.
Home in Davenport
4.93 out of 5 average rating, 14 reviews

BRAND NEW 10Bedrms/Sleeps22 At Windsor Island

AileenRating, 5 stars2 weeks ago
Our stay was fantastic!! Close to all the parks, but with all the amenities here, you can enjoy your entire stay within the community! Perfect for large groups with kids! Game space upstairs is awesome! Would love to stay here again when we are in the area. Highly recommend!
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, 6 reviews

Spacious 4 bedroom single story home

RobertRating, 5 stars3 weeks ago
This home is one the most wonderful place we’ve stayed in. Lovely kitchen complete with so many items to cook a family dinner. Beautiful lanai with comfortable seating and lovely plants. And the back garden is beautiful as well with many flowering plants this time of year. Ronald was very accommodating by solving all the minor problems. Loved our stay here.
Top guest favorite
A light and airy living room features two teal armchairs with patterned pillows beside a modern sofa. A flat-screen TV is mounted on the wall, accompanied by decorative mirrors and subtle lighting. Natural light filters in through large windows framed by striped curtains.
Home in Davenport
5 out of 5 average rating, 81 reviews

5 ⭐️Gorgeous*Gated*15 Min.Disney*Wi-Fi*GameRoom

AmandaRating, 5 stars4 months ago
Excellent space. Close to Disney and other dining options. Nice, gated community. Will recommend!

Private house rentals

Guest favorite
A spacious screened-in patio area surrounds a private pool, offering a serene outdoor retreat. The pool features a light blue surface, with lounge chairs positioned nearby. Lush greenery is visible beyond the enclosure, providing an inviting backdrop.
Home in DeBary
4.92 out of 5 average rating, 26 reviews

Central Florida Pool Home.

RobinRating, 5 stars1 month ago
We truly enjoyed our stay at Jim's. It is a very nice house and well worth the money! Yoburt the cat is awesome company and a great host! Will go back again if we need a place to stay.
Superhost
The exterior of a contemporary two-story home is visible, featuring a light grey facade with white trim. A covered porch with columns and a balcony above is highlighted, surrounded by manicured shrubs and trees. A clear sky and soft clouds provide a bright backdrop.
Home in Four Corners
4.78 out of 5 average rating, 98 reviews

Jas Vacation Home

CarmenRating, 5 stars3 months ago
Great place for my family to spend Christmas together. The place had enough space, quite, easy access, and mostly the kitchen space was more than enough to cook a holiday dinner.
Guest favorite
A heated, screened-in pool area is illuminated by string lights, creating a serene atmosphere. The turquoise water is surrounded by a spacious concrete deck, featuring several lounge chairs. Lush greenery is visible beyond the pool enclosure, enhancing the sense of privacy.
Home in Davenport
4.89 out of 5 average rating, 154 reviews

Private Haven: Free Pool Heat & BBQ/5Bedroom/4.5Ba

NataliaRating, 5 stars1 month ago
Pam’s place was lovely and a perfect place for our vacation. The heated pool was very appreciated, and there were plenty of towels, blankets, soap, dishes, blankets etc. The house was exactly as pictured and very spacious. Pam was very helpful with instructions and checked in regularly. We had no issues during our stay but we felt if anything did occur Pam would have been responsive which was nice to know. We would definitely recommend this place and would stay again if we came back to Orlando.
Superhost
The exterior of a single-story home is visible, featuring a well-maintained lawn and landscaped garden. The façade is painted in light colors with a central entrance highlighted by a blue door. A car is parked on the driveway, which leads to a two-car garage.
Home in Kissimmee
4.89 out of 5 average rating, 28 reviews

Pelican House

WilliamRating, 5 stars1 week ago
We stayed at the Pelican House for three whole months. This home worked well for our extended stay because of its proximity to restaurants, groceries and Disney World! The neighborhood was quiet pretty much every night and having the open green space in the back was really nice, especially when the Sandhill Cranes came by in the mornings. They were awesome to watch. Donna was very responsive to any questions or concerns we had during the stay. She would reply within 10 minutes usually. The biggest benefit for us was proximity to Disney World. We could leave the house and be at the parks within 15-20 minutes most days. Traffic coming back from Disney was typically a challenge, though I feel the whole area in Kissimmee would be the same. All in all, we would absolutely stay at the Pelican house again for any future long-term stay in that area. It worked great for our needs this trip! Thanks Donna!!
Superhost
The spacious living area is furnished with two grey sofas and an armchair featuring a blue pattern. Natural light enters through the windows, illuminating the room. A wooden coffee table sits atop a dark area rug, while artwork is displayed on the walls.
Home in Kissimmee
5 out of 5 average rating, 4 reviews

Sleeps 10 * House + Apt *Pool*Near Disney*GolfView

FrancisRating, 5 stars40 months ago
Walk in the door of the main house and first thing is “wow.” Spaciousness and high ceilings and the view all the way through to the back windows of the golf course was impressive. Neighborhood very walkable and safe Little traffic within the complex for kids. Nice to have easy driveway parking right out front for unloading. Plenty of space to fit my people. Nicely decorated and not full of a bunch of bling on end tables and shelves that the kids would run into and break. I was not just clean but had a sense of clean, design-wise, with the modern but comfy furniture, giant kitchen island, table surfaces… all that and, again, the spaciousness gives you the ability to breathe! But it still had a homey feel – way better than a hotel setting where we would have all been on top of each other. The cute coffee station was a really nice touch with everything you needed right there in one spot off the kitchen. Because the house is set back on the property it was like a real get-away, and with the guest house, my parents were able to have their privacy and we could have ours – when we needed it. The guest house is exactly what they needed. Separated from main house it is perfect for the grandparents to spend alone time with the kids for a while. But it’s also like a real house by itself! Very open and comfortable – and a great view of the action in the pool and courtyard. Pool is just big enough to enjoy and with the protective fence, you don’t really have to worry about the kids running around in the yard – that was also a nice touch. And even though there’s a Wa Wa right outside the complex gate, for quick lunches and coffee – and gas – we discovered an area ChampionsGate, a suburban community with all the restaurants and shops and places to do errands. About a 5-10 minute drive. Lastly, I really liked the big walk-in shower, and my partner absolutely loved the big tub – all that in the en suite bathroom off the master bedroom. It was out of the way and private –  like our own a retreat spot.
Guest favorite
An open-concept living space is shown, featuring a modern kitchen with essential appliances and a breakfast bar. A cozy seating area includes a sofa and television. Natural light enters through large windows, illuminating the laminate flooring. A small dining table is positioned for two.
Home in Apopka
4.94 out of 5 average rating, 197 reviews

Quiet Home Near the Springs

AmparoRating, 5 stars1 week ago
Glenn was nothing but friendly and responsive the entire time we needed something. His home was cute and what we needed for a good nights rest. A cute living area, small kitchen with the basics and a clean bedroom with a comfy bed. Very simple instructions to gain entry and for check out as well. As guests, the best we can do is be amenable and make sure we follow suit.
Guest favorite
A refreshing pool is captured, with sunlight sparkling on the water's surface. The stone-accented summer kitchen with a wooden pergola is visible in the background, along with plants and seating, creating a relaxed outdoor setting.
Home in Casselberry
4.93 out of 5 average rating, 104 reviews

Villa with Guest House & Pool-Patio

MikeRating, 5 stars1 month ago
We were in town for my son’s wedding this past week. We had a variety of family - both old and young - that we were trying to please. This place checked all the boxes we were looking for - spacious, clean, easy to get in and out, great pool and outside area (perfect for relaxing during the day). Lots of little touches as well - soap, shampoo, plenty of towels and extra linens, we even found some sunscreen one afternoon for the pool. We had a great stay and Jose was extremely helpful along the way. Definitely will stay here again in the future as we come back to FL to visit my son and new daughter-in-law! Thank you!
Top guest favorite
A modern exterior features a row of townhomes with a clean white facade. Large windows allow natural light to enter, while pathway and landscaping add an organized aesthetic. The entrance is marked by a sleek door, flanked by decorative elements and privacy walls.
Home in Davenport
5 out of 5 average rating, 5 reviews

318 BD - Disney Dream House

JoaquimRating, 5 stars3 months ago
Edney was an amazing host! His communication was quick and helpful, ensuring we had everything we needed for a comfortable stay. The house was breathtaking – extremely clean, spacious, and thoughtfully designed with every detail in mind. It far exceeded our expectations! We highly recommend staying here and would gladly return in the future. Thank you, Edney, for making our stay unforgettable!

Quick stats about house rentals in Longwood

  • Total rentals

    60 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

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  2. United States
  3. Florida
  4. Seminole County
  5. Longwood
  6. House rentals