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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Longwood vacation rentals

A modern kitchen with a microwave, coffee maker, and potted plants. There is a seating area with a sofa and a coffee table.

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The price is AED 284
AED 598 total
includes taxes & fees
26 Oct - 27 Oct
The Longwood Escape • Modern Private Guesthouse Near Orlando
Terrace/patio

2. The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub

The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
Longwood
8.4 out of 10, Very good, (5 reviews)
"Awesome place to stay! Was well stocked for our big group and plenty of space for everyone to hang out."
United States
Tyler P.
The price is AED 3,425
AED 6,120 total
includes taxes & fees
30 Sep - 1 Oct
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
A swimming pool with a unique light display creating patterns on the water's surface.

3. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is AED 360
AED 888 total
includes taxes & fees
30 Sep - 1 Oct
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A modern kitchen with white cabinets, a microwave, and a green wall with a neon sign.

4. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is AED 281
AED 800 total
includes taxes & fees
30 Sep - 1 Oct
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Private kitchen

5. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (48 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is AED 441
AED 1,184 total
includes taxes & fees
27 Oct - 28 Oct
Florida Vacation with pool fun for families
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

6. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (58 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is AED 479
AED 898 total
includes taxes & fees
6 Oct - 7 Oct
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A backyard with a hammock, outdoor seating, and string lights.

7. 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 264
AED 543 total
includes taxes & fees
7 Oct - 8 Oct
The Jazz Loft
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

8. Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Sanford
9.8 out of 10, Exceptional, (9 reviews)
"Perfect spot for a quick night after your flight into Sanford. Close to the airport, clean accommodations in a quiet neighborhood. Couldn’t ask for more!"
United States
Julia F.
The price is AED 393
AED 514 total
includes taxes & fees
30 Sep - 1 Oct
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A modern kitchen with a marble countertop, gold faucets, and a large window.

9. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (21 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 253
AED 530 total
includes taxes & fees
2 Oct - 3 Oct
Bella Breeze
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

10. 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 281
AED 562 total
includes taxes & fees
30 Sep - 1 Oct
Boho Nights
Private kitchen

11. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is AED 257
AED 487 total
includes taxes & fees
6 Oct - 7 Oct
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A modern kitchen with a central island, built-in appliances, and a skylight.

12. Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (109 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
Stylish Boutique Guest house in Winter Park
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

13. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is AED 281
AED 837 total
includes taxes & fees
1 Oct - 2 Oct
The Blue Aztec
A modern living room with a grey sofa, two armchairs, a coffee table, and a small side table with a lamp. There is a brick fireplace, a kitchen area with a countertop and cabinets, and a large window with blinds.

14. 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 417
AED 775 total
includes taxes & fees
30 Sep - 1 Oct
The Front Porch
Terrace/patio

15. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
West Lakes District
10.0 out of 10, Exceptional, (4 reviews)
"Tammie is an amazing host! Super comfy and cute tiny home! Definitely booking again!"
United States
chelsea
The price is AED 244
AED 492 total
includes taxes & fees
30 Sep - 1 Oct
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

16. Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
The price is AED 430
AED 1,275 total
includes taxes & fees
4 Oct - 5 Oct
Tranquil 3-bedroom house in Sanford with AC, WiFi
IMG 8991

17. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is AED 312
AED 644 total
includes taxes & fees
1 Oct - 2 Oct
The Blue Aztec
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

18. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (334 reviews)
"Establishment with meticulously designed in, which made it very comfortable. I enjoyed my stay tremendously. The communication of the staff was amazing, our room is immaculate, a bar had a very in fighting comforting environment very clean get place to socialize with friends and family.I will see you next year the same time."
United States
Sondria
The price is AED 281
AED 316 total
includes taxes & fees
4 Oct - 5 Oct
Suites by The Wellborn
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

19. Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.6 out of 10, Exceptional, (13 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is AED 386
AED 921 total
includes taxes & fees
30 Sep - 1 Oct
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
A house with a red door, a front porch, and a pathway leading to the entrance.

20. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AED 234
AED 647 total
includes taxes & fees
1 Oct - 2 Oct
Downtown Cottage
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

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?

Salt Pool, cozy House near Downtown and International Airport: This vacation home rental near Longwood is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchenette with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Longwood?

With 32 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 Wekiva River are a couple of lovely local spots to get outside and enjoy nature. Universal Studios Florida and Universal Orlando Resort 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.