A greenhouse with hanging flower baskets and ivy-covered walls.

Longwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Longwood vacation rentals

Interior

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (20 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
The price is AED 281
AED 562 total
includes taxes & fees
6 Aug - 7 Aug
Bella Breeze
Studio | WiFi (free)

2. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is AED 260
AED 566 total
includes taxes & fees
6 Aug - 7 Aug
Cozy Modern Studio
Exterior

3. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
The price is AED 258
AED 536 total
includes taxes & fees
7 Aug - 8 Aug
The Jazz Loft
2 bedrooms, desk, WiFi (free)

4. The Front Porch

The Front Porch
3.0 star property
Downtown Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is AED 456
AED 819 total
includes taxes & fees
13 Aug - 14 Aug
The Front Porch
Interior

5. Totally 80's

Totally 80's
3.0 star property
Sanford
8.6 out of 10, Excellent, (11 reviews)
"Super cute property and fantastic hosts!!"
United States
Angi
The price is AED 226
AED 500 total
includes taxes & fees
6 Aug - 7 Aug
Totally 80's
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

6. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is AED 281
AED 837 total
includes taxes & fees
9 Aug - 10 Aug
The Blue Aztec
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

7. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is AED 270
AED 549 total
includes taxes & fees
13 Aug - 14 Aug
Boho Nights
Standard Apartment | Living area

8. The Mellow Yellow

The Mellow Yellow
3.0 star property
Downtown Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
The price is AED 264
AED 819 total
includes taxes & fees
9 Aug - 10 Aug
The Mellow Yellow
Exterior

9. The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is AED 449
AED 1,025 total
includes taxes & fees
6 Aug - 7 Aug
The Contemporary
Room, 1 King Bed, Non Smoking (High Floor, West View) | WiFi (free), bed sheets

10. The View Hotel, Trademark Collection by Wyndham

The View Hotel, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very Good, (2,111 reviews)
"It was a pleasure staying in this hotel, I loved it"
United States
Iraliz Marie Bonilla
The price is AED 303
AED 341 total
includes taxes & fees
11 Aug - 12 Aug
The View Hotel, Trademark Collection by Wyndham
House | 2 bedrooms, high-speed internet

11. Upstay 2BR Golfer s Retreat w Patio Ventura Resort

Upstay 2BR Golfer s Retreat w Patio Ventura Resort
2.0 star property
Ventura
The price is AED 314
AED 912 total
includes taxes & fees
1 Sep - 2 Sep
Upstay 2BR Golfer s Retreat w Patio Ventura Resort
Apartment, Patio | Private kitchen | Coffee/tea maker

12. Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
4.0 star property
Downtown Orlando
10.0 out of 10, Exceptional, (1 review)
"Very nice place"
United States
John
The price is AED 347
AED 1,412 total
includes taxes & fees
11 Aug - 12 Aug
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Apartment (2 Bedrooms) | Interior

13. Upstay Golfer's Retreat w Patio at Ventura Resort

Upstay Golfer's Retreat w Patio at Ventura Resort
3.5 star property
Ventura
The price is AED 275
AED 843 total
includes taxes & fees
1 Sep - 2 Sep
Upstay Golfer's Retreat w Patio at Ventura Resort
Terrace/patio

14. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.4 out of 10, Very Good, (1,193 reviews)
"I love this hotel, super clean and comfortable"
United States
Raúl
The price is AED 212
AED 283 total
includes taxes & fees
19 Aug - 20 Aug
The Point Hotel & Suites Orlando
The Garden, Pet Friendly | Terrace/patio

15. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (39 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is AED 577
AED 640 total
includes taxes & fees
6 Aug - 7 Aug
Historic Tremain Cottages
Apartment, Patio | Living area

16. Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is AED 369
AED 1,035 total
includes taxes & fees
10 Aug - 11 Aug
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Bar (on property)

17. Premier Resort Condos Near Universal

Premier Resort Condos Near Universal
4.0 star property
Florida Center
8.6 out of 10, Excellent, (28 reviews)
"We had an amazing stay, definitely will visit again"
United States
Cydney
The price is AED 321
AED 605 total
includes taxes & fees
13 Aug - 14 Aug
Premier Resort Condos Near Universal
Studio | Living area

18. Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
3.5 star property
Colonialtown South
The price is AED 1,029
AED 1,409 total
includes taxes & fees
7 Aug - 8 Aug
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
Villa (3 Bedrooms) | Interior

19. The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is AED 496
AED 1,978 total
includes taxes & fees
6 Aug - 7 Aug
The Farm House - Great Location + Pet Friendly!
Cottage, 1 Queen, 2 Twins, Sleeper Sofa, Pet Friendly (235 Cottage) (Ground Floor) | Terrace/patio

20. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is AED 783
AED 870 total
includes taxes & fees
6 Aug - 7 Aug
Mount Dora Cottages
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longwood Hotel Reviews

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"So convenient that it’s right inside the airport; no rushing to catch a shuttle or stressing when you get off the plane. They found us an open room to upgrade to when our plane got in early and we didn’t want to wait around for check in. On site restaurant is really nice too."
Carly 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport

Frequently asked questions

Can I find vacation rentals in Longwood?

Yes, we have vacation rentals near the most popular sights in Longwood, or you can go with a secluded option if you're looking for relaxation. Longwood is known for its shopping and lake views. Make sure you have time to check out the restaurants and golf courses during your trip.

What's the top vacation rental that Longwood has to offer?

Tiny tropical Orlando Univesal-Disney: This vacation home rental near Longwood is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Longwood?

With 30 Expedia vacation rentals, you're sure to find just the right place for your Longwood stay.

What can I see and do in Longwood?

Boombah-Soldiers Creek Park and Big Tree Park are a couple of lovely local spots to get outside and enjoy nature. Kia Center and Orlando International Premium Outlets are other popular places to visit in the area.

What are vacation rentals like in Longwood?

Vacation rentals are private properties you can book for a few days or a quick weekend in Longwood. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.