Holiday Rentals Longwood from £44: Find Short-Term Rentals & Holiday Accommodations

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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

Longwood

includes taxes & fees

30 Nov - 1 Dec

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

Longwood

Wes S.

includes taxes & fees

18 Nov - 19 Nov

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

Longwood

Tyler P.

includes taxes & fees

10 Nov - 11 Nov

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!

Lake Mary

Gary

includes taxes & fees

10 Nov - 11 Nov

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!

Casselberry

Charles T.

includes taxes & fees

10 Nov - 11 Nov

A swimming pool with lounge chairs and palm trees.

6. The Point Hotel & Suites Orlando

Florida Center

Susan

includes taxes & fees

22 Nov - 23 Nov

A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

7. Suites by The Wellborn

Lake Cherokee

Dustin

includes taxes & fees

23 Nov - 24 Nov

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, Trademark Collection by Wyndham

Orlando

Martyn

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a marble countertop, gold faucets, and a large window.

9. Bella Breeze

Downtown Sanford

Sara

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with a central island, built-in appliances, and a skylight.

10. Stylish Boutique Guest house in Winter Park

Winter Park

Amanda B.

includes taxes & fees

10 Nov - 11 Nov

A backyard with a hammock, outdoor seating, and string lights.

11. The Jazz Loft

Downtown Sanford

Tiffany

includes taxes & fees

22 Nov - 23 Nov

A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

12. Boho Nights

Downtown Sanford

Nicholas

includes taxes & fees

4 Dec - 5 Dec

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

Sanford

Julia F.

includes taxes & fees

12 Nov - 13 Nov

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

Downtown Sanford

Johnny

includes taxes & fees

15 Nov - 16 Nov

A resort with a central swimming pool, multiple lounge areas, and a view of the surrounding buildings.

15. Villatel Resort Orlando, Apartments by Marriott Bonvoy

Orlando

Christine

includes taxes & fees

29 Nov - 30 Nov

A poolside area with lounge chairs, a fire pit, and a building in the background.

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

International Drive District

Eyda

includes taxes & fees

29 Nov - 30 Nov

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

Orlando

Kyle Y.

includes taxes & fees

10 Nov - 11 Nov

18. The Blue Aztec

Downtown Sanford

Kael

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a wooden floor, seating areas, and a reception desk.

19. King Bed|Smoking|Orlando

Orlando

Anonymous traveller

includes taxes & fees

10 Nov - 11 Nov

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!

College Park

Raegan S.

includes taxes & fees

10 Nov - 11 Nov

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Find holiday rentals that suit your style

Top Longwood Hotel Reviews

A modern hotel entrance with a covered walkway, large columns, and a clear sky.

Hyatt Place Lake Mary/Orlando North

Lake Mary

10/10 Excellent

CRAIG

A breakfast bar with a coffee machine, a waffle display, and a glass display case with pastries.

La Quinta Inn & Suites by Wyndham Orlando Lake Mary

Lake Mary

10/10 Excellent

Enjoy a one night stay on drive through from Orlando airport to somewhere & again on way back to airport after holiday. Very quiet area, always nice welcome with friendly people. Good sized rooms with comfortable beds/nice bathroom and amenities ie fridge/microwave/coffee machine. Reception & dining area pleasant and a good choice for breakfast. Like the outside garden section too with it's pool and hot tub. Only thing I think would be most welcome would be some umbrellas for sun shade by the...

Judith

A modern lobby with a reception desk, seating area, and decorative columns.

Hilton Orlando/Altamonte Springs

Altamonte Springs

10/10 Excellent

A truly remarkable franchisee run Hilton. The place is absolutely spotlessly clean and very well maintained throughout. Attention to fine detail is clearly the order of the day here. By far the best asset are the staff. They have been well schooled in engaging with guests with a warm and friendly greeting each and every time and you get a real sense that your patronage is truly valued. Well done to the Cooper family who owns the place and the management and staff who are delivering an...

David

A modern lobby with a sofa, chairs, a reception desk, and a patterned carpet.

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Sanford

10/10 Excellent

Julian

An outdoor patio area with seating, a bar, and a fire feature.

Hyatt House Orlando Airport

Airport North

10/10 Excellent

Kelly

An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

10/10 Excellent

Mark

A Holiday Inn Express building with a modern design, featuring a prominent entrance and a covered walkway.

Holiday Inn Express Orlando International Airport by IHG

Orlando

10/10 Excellent

Lauren

A modern hotel with a red carpet leading to the entrance, a wooden walkway, and a clear view of the building's facade.

EVEN Hotel Orlando International Airport by IHG

Airport North

10/10 Excellent

john

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, apart-hotels, 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 £44 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.

Search Holiday Rentals in Longwood

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Longwood holiday rentals

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

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

3. The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub

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

5. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

6. The Point Hotel & Suites Orlando

7. Suites by The Wellborn

8. The View Hotel, Trademark Collection by Wyndham

9. Bella Breeze

10. Stylish Boutique Guest house in Winter Park

11. The Jazz Loft

12. Boho Nights

13. Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

14. The Front Porch

15. Villatel Resort Orlando, Apartments by Marriott Bonvoy

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

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

18. The Blue Aztec

19. King Bed|Smoking|Orlando

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

Find holiday rentals that suit your style

Top Longwood Hotel Reviews

Hyatt Place Lake Mary/Orlando North

10/10 Excellent

Find out more about Longwood

Longwood holiday rentals: An excellent choice for every season

How to find incredible deals on Longwood rentals

Frequently Asked Questions

Can I find holiday rentals in Longwood?

What are some of the best holiday rentals that Longwood has to offer?

How many holiday rentals are there in Longwood?

What can I see and do in Longwood?

What are holiday rentals like in Longwood?