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

Longwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Longwood vacation rentals

Private kitchen

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The price is ￥11,765
￥25,293 total
includes taxes & fees
Sep 13 - Sep 14
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
7.4 out of 10, Good, (3 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 ￥148,651
￥280,633 total
includes taxes & fees
Aug 19 - Aug 20
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
Outdoor pool

3. Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (64 reviews)
"Everything was great as usual!!"
United States
Christine B.
The price is ￥17,924
￥42,859 total
includes taxes & fees
Aug 19 - Aug 20
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Smart TV, fireplace, video games

4. Early Check In Lake Mary Last-Minute Deal!

Early Check In Lake Mary Last-Minute Deal!
Lake Mary
10.0 out of 10, Exceptional, (20 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is ￥14,204
￥37,750 total
includes taxes & fees
Aug 19 - Aug 20
Early Check In Lake Mary Last-Minute Deal!
3 bedrooms, desk, iron/ironing board, WiFi (free)

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, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is ￥20,791
￥40,399 total
includes taxes & fees
Aug 19 - Aug 20
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Property grounds

6. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is ￥21,841
￥57,781 total
includes taxes & fees
Sep 1 - Sep 2
Incredible Private Lakefront Cottage Retreat
Coffee/tea maker, fridge, microwave, oven

7. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (46 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is ￥17,217
￥51,805 total
includes taxes & fees
Sep 16 - Sep 17
Florida Vacation with pool fun for families
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

8. 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 ￥11,700
￥23,812 total
includes taxes & fees
Aug 30 - Aug 31
Boho Nights
Interior

9. 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 ￥12,188
￥24,359 total
includes taxes & fees
Aug 28 - Aug 29
Bella Breeze
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

10. 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 ￥11,192
￥35,206 total
includes taxes & fees
Aug 19 - Aug 20
The Blue Aztec
Coffee/tea maker, fridge, microwave, paper towels

11. Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Sanford
10.0 out of 10, Exceptional, (8 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 ￥21,004
￥26,714 total
includes taxes & fees
Sep 16 - Sep 17
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Dining

12. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (20 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is ￥19,370
￥33,971 total
includes taxes & fees
Aug 24 - Aug 25
River City Retreat
Exterior

13. 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 ￥10,912
￥22,935 total
includes taxes & fees
Aug 19 - Aug 20
The Jazz Loft
Terrace/patio

14. 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 ￥12,427
￥26,664 total
includes taxes & fees
Aug 19 - Aug 20
The Blue Aztec
3 bedrooms, desk, iron/ironing board, WiFi

15. 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 home! My friends and I had such an amazing time and I loved the dog bed & bowls for my dog Venus who stayed with us"
United States
Janelle G.
The price is ￥18,652
￥58,832 total
includes taxes & fees
Aug 19 - Aug 20
Tranquil 3-bedroom house in Sanford with AC, WiFi
Exterior detail

16. Downtown Cottage

Downtown Cottage
Colonialtown North
8.6 out of 10, Excellent, (14 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥9,485
￥27,310 total
includes taxes & fees
Aug 23 - Aug 24
Downtown Cottage
2 bedrooms, desk, WiFi (free)

17. 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 ￥18,093
￥33,657 total
includes taxes & fees
Aug 19 - Aug 20
The Front Porch
1 bedroom, desk, iron/ironing board, WiFi (free)

18. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (63 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is ￥9,894
￥20,951 total
includes taxes & fees
Aug 31 - Sep 1
Private guest studio in the heart of orlando.
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is ￥16,729
￥41,524 total
includes taxes & fees
Aug 19 - Aug 20
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
1 bedroom, desk, iron/ironing board, WiFi (free)

20. Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.8 out of 10, Exceptional, (16 reviews)
"Just what we needed for our quick trip to Orlando! super communicative host and very nice area. Would love to stay here again if given the chance!"
United States
Liv B.
The price is ￥10,754
￥27,832 total
includes taxes & fees
Aug 31 - Sep 1
Yania's Cozy 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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Top Longwood Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Good"
Javier Dalian 2-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

Find out more about Longwood

Search for holiday rentals in Longwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Longwood using one of the methods below:

  • View our selection of featured holiday rentals in Longwood
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  • Enter your travel dates to view the best deals on holiday rentals in Longwood while they last

Look no further and take a look at our great range of rental properties in Longwood!

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 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 Spring Hammock Preserve 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.