House holiday 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

Guest favourite
Home in Orlando
4.88 out of 5 average rating, 124 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

SuzanneRating, 5 stars4 days ago
Had a nice stay with family and friends at Alyssa’s place along with 2 dogs. Was so nice to be able to bring out pets along on vacation. The house was clean, beds were comfortable, lots of space. I Spent most of my time out in the pool which was amazing.
Superhost
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 favourite
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 favourite
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 favourite
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 favourite
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!
Superhost
Home in Apopka
4.84 out of 5 average rating, 119 reviews

2-bedroom home with pool near Kings Landings!

AshtonRating, 5 stars2 weeks ago
We had an absolutely wonderful stay at this property! Very clean and cozy, making it easy to relax and feel at home. The pool was a major highlight! It was well-maintained, refreshing, and the perfect place to unwind under the sun. We loved spending our afternoons there. The area was incredibly peaceful, offering an escape from the hustle and bustle. Very quiet and secluded neighborhood. We couldn’t have asked for a better experience and would love to return in the future. Highly recommend!
Guest favourite
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!! 😁

Weekly house rentals

Guest favourite
Home in Casselberry
4.96 out of 5 average rating, 47 reviews

Luxurious lakefront home near DT and Winter Park

CatherineRating, 5 stars1 month ago
We had a lovely stay. It was so nice to come home to a clean comfortable home away from home at the end of the day. I love the decor!
Top Guest favourite
Home in Longwood
4.94 out of 5 average rating, 35 reviews

Central Florida Pool Home

LisaRating, 5 stars1 week ago
We were in the area for a softball tournament at the Seminole Softball complex which was a short drive away! Travis was an excellent and friendly host who answered all questions. We have stayed in a lot of Airbnb’s and this has to be the cleanest one we have stayed in! Everything was squeaky clean outside and inside! Home is well decorated, set up for entertainment and had everything we needed to be feel comfortable and at home. The pool was a perfect temperature and made me feel like I was in a backyard oasis! The screened in patio was perfect for having a few drinks while watching games on the very large TV and grilling hamburgers using one of the 3 options of grills provided. My daughter, husband and I enjoyed the Bocce Court as well as cornhole boards! To top it all off the beds and living room couch were super super comfortable! We throughly enjoyed our stay, this home is in our top 3 we have stayed. We will definitely book again when in the area! Thank you so much!
Guest favourite
Home in Winter Park
4.95 out of 5 average rating, 20 reviews

New built Private Studio Orlando/Winter Park area

GregoryRating, 5 stars4 weeks 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 favourite
Home in Casselberry
4.92 out of 5 average rating, 25 reviews

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

DebbieRating, 5 stars1 week ago
The palace looked exactly like your pictures! The pool was perfect! Great communication
Guest favourite
Home in Lake Mary
4.97 out of 5 average rating, 90 reviews

Cozy, Stylish & Charming Home

RossibellyRating, 5 stars1 week ago
My family and me recently had the pleasure of staying in this cozy and warm house, and it was everything we hoped for and more. It was the perfect spot for our family trip to Florida. The house was exactly as described - cozy, clean and incredible welcoming. From the moment we walked in, felt right at home. The interior was thoughtfully decorated with charming, rustic touches and soft lighting that created an inviting atmosphere. This Airbnb had everything we needed for a comfortable family trip, from a well-equipped kitchen for cooking meals, to spacious bedrooms and plenty of thoughtful touches throughout. The bedrooms were comfortable with soft linens and plenty of blankets in case is needed. The living space was just the right size for us, to chill and relax. But what we loved the most was the patio – it was the perfect place to enjoy our morning coffee or unwind in the evenings after a day out. Santiago, the host went above and beyond to make sure we had a great stay.
Guest favourite
Home in Altamonte Springs
4.95 out of 5 average rating, 86 reviews

Orlando Poolside Oasis

DarielRating, 5 stars2 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.
Guest favourite
Home in Altamonte Springs
4.93 out of 5 average rating, 44 reviews

Lakefront House ~ Pool ~ 5 Star Location

JonRating, 5 stars1 week ago
WOW! What a great place. Very picturesque. Enjoyed the lakefront, pool, private. Location is close to the Altamonte Mall and alot of retail, restaurants, etc - however, the location is tucked away and you would never know it.
Guest favourite
Home in Casselberry
4.83 out of 5 average rating, 29 reviews

Stylish and cozy townhome!

SherieRating, 5 stars1 week ago
The townhome was clean and in a safe neighborhood! It was stocked with everything we needed to feel at home. The beds and couches were comfy, which is a big plus as well! Grace was quick to respond when we had questions and was super friendly!

Private house rentals

Guest favourite
Home in Lake Mary
5 out of 5 average rating, 12 reviews

Casa Alma Vacation Home

TimRating, 5 stars2 months ago
Great home. We were a group of 8 and the home did not feel crowded. Kitchen was a beautiful space and open enough for us all to hang out. Host was very kind and responsive. Yard is spacious. Nice quiet neighborhood. Would definitely recommend and stay again!
Guest favourite
Home in Altamonte Springs
4.93 out of 5 average rating, 44 reviews

Secluded Pool Getaway

KyleRating, 5 stars3 weeks ago
10/10 great place to stay! Everything from checkin to checkout was so easy and smooth and exactly what we wanted for the weekend. Spacious, comfortable, and feels like home. Thank you! Definitely recommend.
Guest favourite
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.
Superhost
Home in Altamonte Springs
4.75 out of 5 average rating, 12 reviews

Stylish and Cozy Castle near EPIC Universe Park!

RyanRating, 5 stars1 month ago
upon arrival the bottom lock on the door was keeping me from getting inside not even 60 seconds after i text deja she gave me a solution and i was inside in no time. there was no paper towels when we got there but deja was SUPER fast to get some more delivered to the house and also through in some bottled water for me and my girl. Deja is a great host with great communication and will make sure your stay is worth every penny!
Guest favourite
Home in Sanford
4.93 out of 5 average rating, 69 reviews

Generations Gateway (Pool/Sauna)

DeborahRating, 5 stars3 days ago
We were so excited for our week celebrating our son’s wedding. The house was perfect for our family (4 adults and 2 toddlers). The pool was a bonus for the hot summer days and the outdoor blackstone was a pleasure to bbq on. The house was equipped with items for the littles (pack-n-play, high chair, outdoor chalk and pool toys). We will definitely be staying here again.
Guest favourite
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 !
Superhost
Home in Longwood
5 out of 5 average rating, 5 reviews

Lakefront Home Where You Can Retreat and Relax

MarkRating, 5 stars5 months ago
Great house with tons of space and a pretty lake view out back. Nice that the master is on the opposite end of the house from the rest of the guests. House was in excellent condition, in a quiet neighborhood, and the host was so helpful....even had coffee, crib sheets, and a high chair delivered (so our little one had a place to eat). We would recommend this to anyone.
Top Guest favourite
Home in Apopka
4.97 out of 5 average rating, 60 reviews

Best of Both Worlds Lakehouse

BobbyRating, 5 stars3 days ago
We had the best time here! It was the best base camp for our family vacation; two kids wanted to do universal and others spent all day fishing and was very successful! We literally used every part of the house and it was great - used the paddle boards multiple times a day, played games in the game room, grilled and family dinners, lounged on the sofas for movies and plenty of space for sleeping. Great community, very safe and peaceful neighborhood; easy Walmart grocery deliveries. Highly recommend!

Quick stats about house rentals in Longwood

  • Total rentals

    60 properties

  • Nightly prices starting at

    $17 NZD 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

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