Longwood Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Longwood holiday rentals

A hallway with a large wall clock, wicker baskets, a potted plant, and a door leading to a room with a chair and a small table.

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The price is NZ$281
includes taxes & fees
30 Nov - 1 Dec
The Longwood Escape • 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 NZ$482
includes taxes & fees
18 Nov - 19 Nov
Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games
A two-story house with a driveway leading to a garage, surrounded by trees and a landscaped garden.

3. 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 NZ$3,002
includes taxes & fees
9 Nov - 10 Nov
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
Relax in a cozy, candle-lit living space with plush seating and warm a lighting.

4. 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, (69 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 NZ$447
includes taxes & fees
9 Nov - 10 Nov
Orlando 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 NZ$434
includes taxes & fees
9 Nov - 10 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

6. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (344 reviews)
"The check in process was smooth and did not require any front desk it was perfect for a quick stay! The room was pretty big for the price! and very clean. The property itself was cute and cozy they had a very cool common area! Love this stay"
United States
Dustin
The price is NZ$137
includes taxes & fees
23 Nov - 24 Nov
Suites by The Wellborn
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, 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 NZ$267
includes taxes & fees
15 Nov - 16 Nov
Bella Breeze
A modern living room with a large TV, a fireplace, and a ceiling fan.

8. Walk into Tropical Paradise - POOL - GYM - HOT TUB

Walk into Tropical Paradise - POOL - GYM - HOT TUB
Altamonte Springs
9.6 out of 10, Exceptional, (32 reviews)
"Great stay. Very accommodating! Awesome water pressure!"
United States
William M.
Walk into Tropical Paradise - POOL - GYM - HOT TUB
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, Excellent, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
The price is NZ$262
includes taxes & fees
5 Dec - 6 Dec
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, 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 NZ$238
includes taxes & fees
9 Nov - 10 Nov
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

11. 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$285
includes taxes & fees
4 Dec - 5 Dec
Boho Nights
Private kitchen

12. 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
9.4 out of 10, Exceptional, (9 reviews)
"It is very close to the restaurant, shops and parks"
United States
Naiviv
The price is NZ$239
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
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.

13. 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$406
includes taxes & fees
15 Nov - 16 Nov
The Front Porch
A swimming pool with lounge chairs and palm trees.

14. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,493 reviews)
"This is a great place to stay"
United States
Susan
The price is NZ$147
includes taxes & fees
22 Nov - 23 Nov
The Point Hotel & Suites Orlando
IMG 8991

15. 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 NZ$312
includes taxes & fees
15 Nov - 16 Nov
The Blue Aztec
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
Tranquil 3-bedroom house in Sanford with AC, WiFi
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 NZ$445
includes taxes & fees
12 Nov - 13 Nov
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
A bedroom with a bed, a ceiling fan, a stained glass window, and a door leading to another room.

18. TINY unit in cottage in the middle of Downtown

TINY unit in cottage in the middle of Downtown
Downtown Orlando
9.8 out of 10, Exceptional, (24 reviews)
"The unit was nice and clean. It was a close walk to the Kia Center. In a pretty quiet area."
United States
Paula
The price is NZ$306
includes taxes & fees
17 Nov - 18 Nov
TINY unit in cottage in the middle of Downtown
Exterior

19. Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.6 out of 10, Exceptional, (40 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is NZ$235
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom apartment in house with AC, WiFi included
A spacious lobby with a wooden floor, seating areas, and a reception desk.

20. King Bed|Smoking|Orlando

King Bed|Smoking|Orlando
Orlando
10.0 out of 10, Exceptional, (26 reviews)
"Nearby attractions are close enough to visit without any trouble at all!"
United States
Anonymous traveller
The price is NZ$106
includes taxes & fees
9 Nov - 10 Nov
King Bed|Smoking|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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Find holiday rentals that suit your style

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Top Longwood Hotel Reviews

A multi-story hotel with a modern design, featuring balconies and a covered entrance.
Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
Ivanhoe Village

10/10 Excellent

Good staff
Australia
Charles
Reviewed June 6, 2026
Courtyard by Marriott Orlando Downtown

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$137 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?

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 32 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.