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

Longwood Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Longwood holiday 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 AU$237
includes taxes & fees
29 Sept - 30 Sept
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
8.0 out of 10, 4, (4 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 AU$2,417
includes taxes & fees
16 Sept - 17 Sept
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, 66, (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 AU$324
includes taxes & fees
21 Sept - 22 Sept
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, 21, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is AU$311
includes taxes & fees
16 Sept - 17 Sept
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

5. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, 48, (48 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is AU$468
includes taxes & fees
16 Sept - 17 Sept
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, 56, (56 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is AU$350
includes taxes & fees
16 Sept - 17 Sept
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A modern kitchen with a marble countertop, gold faucets, and a large window.

7. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, 21, (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 AU$213
includes taxes & fees
30 Sept - 1 Oct
Bella Breeze
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

8. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, 16, (16 reviews)
"Great stay!"
United States
Nicholas
The price is AU$213
includes taxes & fees
21 Sept - 22 Sept
Boho Nights
A backyard with a hammock, outdoor seating, and string lights.

9. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, 9, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
The price is AU$200
includes taxes & fees
16 Sept - 17 Sept
The Jazz Loft
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

10. 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, 9, (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 AU$198
includes taxes & fees
17 Sept - 18 Sept
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

11. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, 14, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is AU$312
includes taxes & fees
21 Sept - 22 Sept
The Blue Aztec
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

12. River City Retreat

River City Retreat
Sanford
9.6 out of 10, 21, (21 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is AU$300
includes taxes & fees
21 Sept - 22 Sept
River City Retreat
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

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

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, 28, (28 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
The price is AU$505
includes taxes & fees
17 Sept - 18 Sept
Tranquil 3-bedroom house in Sanford with AC, WiFi
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, 5, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is AU$314
includes taxes & fees
16 Sept - 17 Sept
The Front Porch
A modern kitchen with a dining area, a black sofa, and a painting of a sunset.

15. Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
10.0 out of 10, 22, (22 reviews)
"Super cute would stay here again"
United States
Kristen a.
The price is AU$235
includes taxes & fees
16 Sept - 17 Sept
Cozy studio in fabulous Orlando close to everything
A house with a red door, a front porch, and a pathway leading to the entrance.

16. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, 15, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AU$248
includes taxes & fees
16 Sept - 17 Sept
Downtown Cottage
A covered porch with two blue chairs and a small table, wooden flooring, and a door with a 'Home Sweet Home' sign.

17. Historic Hotspot • Walk to Downtown Fun • Luxury Beds

Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Downtown Sanford
10.0 out of 10, 19, (19 reviews)
"Ideal location, easy walk to food and fun."
United States
Steven H.
The price is AU$315
includes taxes & fees
22 Sept - 23 Sept
Historic Hotspot • Walk to Downtown Fun • Luxury Beds
A modern hotel room with a bed, white curtains, a small desk with a lamp, a refrigerator, and a microwave.

18. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, 65, (65 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is AU$195
includes taxes & fees
16 Sept - 17 Sept
Private guest studio in the heart of orlando.

19. 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
10.0 out of 10, 6, (6 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is AU$188
includes taxes & fees
24 Sept - 25 Sept
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

20. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, 15, (15 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is AU$247
includes taxes & fees
21 Sept - 22 Sept
The Blue Aztec
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

Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

10/10 Excellent
"Cool"
Valeria 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Orlando Airport, FL

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 favourite 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 depend 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 AU$107 per night. Entering your travel dates in the search wizard might find you 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?

Salt Pool, cozy House near Downtown and International Airport: This holiday home rental outside of Longwood is located in the city centre, and has a garden, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Longwood?

With 31 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 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 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.