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

Longwood Holiday Rentals

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Our top choices for Longwood holiday rentals

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The Longwood Escape • Modern Private Guesthouse Near Orlando

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 NZ$3,261
includes taxes & fees
11 Aug - 12 Aug
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub

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, (63 reviews)
"Everything was great as usual!!"
United States
Christine B.
The price is NZ$450
includes taxes & fees
15 Aug - 16 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

4. Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits

Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
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 NZ$398
includes taxes & fees
17 Aug - 18 Aug
Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits

5. 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 NZ$632
includes taxes & fees
25 Aug - 26 Aug
Incredible Private Lakefront Cottage Retreat

6. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (44 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is NZ$568
includes taxes & fees
11 Aug - 12 Aug
Florida Vacation with pool fun for families

7. 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 NZ$429
includes taxes & fees
10 Aug - 11 Aug
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

8. 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 NZ$223
includes taxes & fees
5 Sept - 6 Sept
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

9. 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 NZ$237
includes taxes & fees
15 Aug - 16 Aug
Totally 80's

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 NZ$256
includes taxes & fees
18 Aug - 19 Aug
Boho Nights

11. 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 NZ$383
includes taxes & fees
15 Aug - 16 Aug
The Blue Aztec

12. 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 NZ$248
includes taxes & fees
9 Aug - 10 Aug
The Jazz Loft

13. 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 NZ$260
includes taxes & fees
18 Aug - 19 Aug
Bella Breeze

14. 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 NZ$441
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

15. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
The price is NZ$298
includes taxes & fees
14 Aug - 15 Aug
The Blue Aztec

16. 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 NZ$362
includes taxes & fees
16 Aug - 17 Aug
River City Retreat

17. 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 NZ$615
includes taxes & fees
18 Aug - 19 Aug
Tranquil 3-bedroom house in Sanford with AC, WiFi

18. 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 NZ$297
includes taxes & fees
10 Aug - 11 Aug
Yania's Cozy Getaway

19. 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 NZ$376
includes taxes & fees
10 Aug - 11 Aug
The Front Porch

20. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (62 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is NZ$220
includes taxes & fees
17 Aug - 18 Aug
Private guest studio in the heart of orlando.
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

Find out more about Longwood

Everything you need to know about Longwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Longwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Longwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Longwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Longwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Longwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Longwood holiday rentals we have selected for you start as low as NZ$139 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Longwood rentals

At Expedia, we put the best Longwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Longwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Longwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Longwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Longwood?

Yes, there are holiday rentals close to the most popular sights in Longwood, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Longwood has to offer?

Tiny tropical Orlando Univesal-Disney: This holiday home rental outside of 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 holiday rentals are there in Longwood?

With 30 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Longwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longwood. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.