Longwood Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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 ā€¢ Modern Private Guesthouse Near Orlando

The Longwood Escape ā€¢ Modern Private Guesthouse Near Orlando
Longwood
The Longwood Escape ā€¢ Modern Private Guesthouse Near Orlando
A kitchen with granite countertops, two coffee makers, a sink, wooden cabinets, and a window with white curtains.

2. Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games

Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games
Longwood
9.2 out of 10, Wonderful, (17 reviews)
"It was very nice. It had everything we needed and we will stay there again. Our kids had so much fun in the game room."
United States
Wes S.
The price is SARĀ 340
SARĀ 1,037 total
includes taxes & fees
18 Nov - 19 Nov
Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games
Terrace/patio

3. The American Dream House ā€“ Lakefront Luxury with 2 Heated Pools & Hot Tub

The American Dream House ā€“ 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 SARĀ 4,117
SARĀ 7,111 total
includes taxes & fees
15 Nov - 16 Nov
The American Dream House ā€“ Lakefront Luxury with 2 Heated Pools & Hot Tub
A swimming pool with a unique light display creating patterns on the water's surface.

4. Disney Pool Days & Hammock Naps Book Your Escape NOW!

Disney Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (71 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is SARĀ 409
SARĀ 942 total
includes taxes & fees
1 Dec - 2 Dec
Disney Pool Days & Hammock Naps Book Your Escape NOW!
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

5. 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)
"Everything about the house was great. Great house for the price!"
United States
Charles T.
The price is SARĀ 456
SARĀ 865 total
includes taxes & fees
17 Nov - 18 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A swimming pool with lounge chairs and palm trees.

6. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,512 reviews)
"This is a great place to stay"
United States
Susan
The price is SARĀ 243
SARĀ 320 total
includes taxes & fees
29 Nov - 30 Nov
The Point Hotel & Suites Orlando
A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

7. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (347 reviews)
"Very clean and nice stay"
United States
Wade
The price is SARĀ 253
SARĀ 285 total
includes taxes & fees
29 Nov - 30 Nov
Suites by The Wellborn
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

8. The View Hotel Orlando, Trademark Collection by Wyndham

The View Hotel Orlando, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very good, (2,231 reviews)
"Great stay Large comfortable.room Reasonable price"
United States
Martyn
The price is SARĀ 300
SARĀ 338 total
includes taxes & fees
13 Dec - 14 Dec
The View Hotel Orlando, Trademark Collection by Wyndham
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, (23 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 SARĀ 338
SARĀ 631 total
includes taxes & fees
13 Dec - 14 Dec
Bella Breeze
A modern kitchen with a central island, built-in appliances, and a skylight.

10. Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (110 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
Stylish Boutique Guest house in Winter Park
A backyard with a hammock, outdoor seating, and string lights.

11. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (10 reviews)
"The loft bed was a little difficult so we ended up sleeping on the pullout couch bed instead. 4th Street Live was cool."
United States
Kelly
The price is SARĀ 238
SARĀ 519 total
includes taxes & fees
16 Nov - 17 Nov
The Jazz Loft
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

12. 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 SARĀ 304
SARĀ 593 total
includes taxes & fees
16 Nov - 17 Nov
Boho Nights
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

13. 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, (10 reviews)
"Perfect spot for a quick night after your flight into Sanford. Close to the airport, clean accommodations in a quiet neighborhood. Couldnā€™t ask for more!"
United States
Julia F.
The price is SARĀ 402
SARĀ 495 total
includes taxes & fees
15 Nov - 16 Nov
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
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 SARĀ 405
SARĀ 769 total
includes taxes & fees
15 Nov - 16 Nov
The Front Porch
A poolside area with lounge chairs and a tiled floor.

15. Villatel Resort Orlando, Apartments by Marriott Bonvoy

Villatel Resort Orlando, Apartments by Marriott Bonvoy
4.0 star property
Orlando
9.2 out of 10, Wonderful, (256 reviews)
"This place was great!"
United States
Christine
The price is SARĀ 972
SARĀ 1,284 total
includes taxes & fees
18 Nov - 19 Nov
Villatel Resort Orlando, Apartments by Marriott Bonvoy
A poolside area with lounge chairs, a fire pit, and a building in the background.

16. Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort

Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
3.5 star property
International Drive District
9.2 out of 10, Wonderful, (284 reviews)
"Excelente"
United States
Eyda
The price is SARĀ 568
SARĀ 723 total
includes taxes & fees
13 Dec - 14 Dec
Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

17. 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 SARĀ 394
SARĀ 922 total
includes taxes & fees
11 Dec - 12 Dec
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
IMG 8991

18. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (17 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is SARĀ 357
SARĀ 647 total
includes taxes & fees
19 Nov - 20 Nov
The Blue Aztec
A spacious lobby with a wooden floor, seating areas, and a reception desk.

19. King Bed|Smoking|Orlando

King Bed|Smoking|Orlando
Orlando
9.6 out of 10, Exceptional, (28 reviews)
"The price is good but that is all."
United States
Robert
King Bed|Smoking|Orlando
A living room with a black leather sofa, a white coffee table, and a potted plant. There is a ceiling fan, a TV, and a door leading to a balcony with outdoor furniture.

20. The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
College Park
10.0 out of 10, Exceptional, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
The price is SARĀ 668
SARĀ 1,269 total
includes taxes & fees
16 Nov - 17 Nov
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
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.
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Find vacation rentals that suit your style

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Top Longwood Hotel Reviews

A bar area with a long counter, multiple stools, and shelves with bottles.
Hyatt Place Lake Mary/Orlando North

Hyatt Place Lake Mary/Orlando North

Hyatt Place Lake Mary/Orlando North
Lake Mary

10/10 Excellent

Nice place. Absolutely loved the gym.
United States
Ian
Reviewed June 5, 2024
Hyatt Place Lake Mary/Orlando North

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.