Photo by Kara Akers

Search Villas in Longwood

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Villas in Longwood

7BR Lakefront Duplex w/ Pool, Sauna & Hot Tub!

9.6 out of 10, Exceptional, (15)
"We stayed here for a golf trip in Orlando and it is fantastic property for a large group with plenty of spacious bedrooms and top notch amenities to offer."
The price is SAR 1,084
SAR 2,448 total
includes taxes & fees
31 Jul - 1 Aug
7BR Lakefront Duplex w/ Pool, Sauna & Hot Tub!

Lakefront Villa at a Prime Location

9.0 out of 10, Wonderful, (54)
"Old property but close to convention center"
Lakefront Villa at a Prime Location

Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!

10.0 out of 10, Exceptional, (3)
"We absolutely loved our stay and it was nice and close to the Winter Park restaurants (Park Ave), Rollins College; as well as, has a nice lake/park to go walking nearby. Quiet neighborhood and the outdoor pool/spa was a nice retreat after a busy day. "
The price is SAR 2,157
SAR 4,137 total
includes taxes & fees
28 Jul - 29 Jul
Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!

Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs

Beautiful Lakefront Home w/ Pool in delightful Altamonte Springs

At Lakes Upscale Villa/Next to Downtown Orlando

9.8 out of 10, Exceptional, (7)
"House is beautiful and great location to downtown. We will definitely look at coming back."
At Lakes Upscale Villa/Next to Downtown Orlando

Majestic Dreams

4.0 star property
9.4 out of 10, Exceptional, (18)
"This place was very clean, nice area. "
Majestic Dreams

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

9.0 out of 10, Wonderful, (2)
"The stay was great. There was a slight smell of a chemical odor but not overwhelming. The bed was comfy with clean sheets and there were enough clean towels. Made friends with the local cat. Overall, its was a great stay!"
The price is SAR 334
SAR 723 total
includes taxes & fees
24 Jul - 25 Jul
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Beautiful Lakefront Villa - 5 Minutes to the Attractions!

9.0 out of 10, Wonderful, (176)
"Located near lots of restaurants and close to the convention center. Great value for the price!"
Beautiful Lakefront Villa - 5 Minutes to the Attractions!

Elegant and Spacious 3BD Town Home With CDC Standards - Close to Convention Center #3vc007

3.5 star property
10.0 out of 10, Exceptional, (1)
"The property is perfectly located for universal, seaworld & Disney, all within 10- 15min drive. Based on a complex the pool is approx 5min walk. The facilities are nice and clean. "
Elegant and Spacious 3BD Town Home With CDC Standards - Close to Convention Center #3vc007

Vista Cay Modern

4.0 star property
10.0 out of 10, Exceptional, (3)
Vista Cay Modern

All-new Mid Century Modern Penthouse 3 Bedroom Home by RedAwning

3.5 star property
All-new Mid Century Modern Penthouse 3 Bedroom Home by RedAwning

Banana Leaf Villa- Book your gathering today!

2.0 star property
8.0 out of 10, Very Good, (3)
"The management team was superb. She was very helpful and even went above me expectations."
The price is SAR 296
SAR 403 total
includes taxes & fees
28 Jul - 29 Jul
Banana Leaf Villa- Book your gathering today!

Emerald Isle

3.5 star property
10.0 out of 10, Exceptional, (2)
"Spacious area with 3 floors. It was well organized, but one conplaint was that there were many ants. Other than that, the place was beautiful. Would recommend. "
Emerald Isle

Cozy One Bedroom Lakefront Villa Close to the Attractions

8.8 out of 10, Excellent, (43)
"The owner is very nice and responsive. However, the property is tiny."
Cozy One Bedroom Lakefront Villa Close to the Attractions

Gator Palace: Stylish 5-bedroom, 4-bath home, with upstairs loft. Sleeps 12.

9.4 out of 10, Exceptional, (42)
"Worked well for our team. Lots of room for teenagers to lay around"
Gator Palace: Stylish 5-bedroom, 4-bath home, with upstairs loft. Sleeps 12.

Enchanted 2 Bedroom Home near Downtown Winter Garden

10.0 out of 10, Exceptional, (3)
"Very nice, clean house. Neighborhood was walkable and felt safe. Well equipped kitchen, provided some coffee, oatmeal and snacks which was great for us in the mornings. "
Enchanted 2 Bedroom Home near Downtown Winter Garden

Charming Winter Park 3 Bedroom Villa with Pool

9.8 out of 10, Exceptional, (9)
"Great, quiet little spot. Had everything we needed. Great location too! "
Charming Winter Park 3 Bedroom Villa with Pool

Banana Leaf Villa- Book your gathering today!

2.0 star property
8.0 out of 10, Very Good, (1)
The price is SAR 296
SAR 403 total
includes taxes & fees
28 Jul - 29 Jul
Banana Leaf Villa- Book your gathering today!

Banana Leaf Villa- Book your gathering today!

2.0 star property
6.0 out of 10, (2)
"Lovely, relaxing piece of property. The staff was very nice. Never saw any other guests during our stay so it felt like we had the whole place to ourselves. Would stay here again in a heartbeat. There was a mini fridge in the room and a hairdryer in the bathroom. It was very clean and taken care of."
The price is SAR 296
SAR 403 total
includes taxes & fees
28 Jul - 29 Jul
Banana Leaf Villa- Book your gathering today!

Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!

6.4 out of 10, (5)
"The house it a bit outdated. It was clean and comfortable but the couch was all torn up and the bathrooms had some issues with plumbing. "
Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Longwood Hotel Reviews

Frequently asked questions

Why book your villa in Longwood with Expedia?
Booking a villa in Longwood is as simple as deciding on your travel dates and choosing a place that checks your boxes. On the lookout for something affordable or luxurious, or a property that also features a pool and free WiFi? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Longwood?
A fantastic way to zero in on cheap villas in Longwood is with Expedia's useful filter tool. Narrow down your search by amenities, star rating and budget to nab awesome prices in just a couple of clicks.