Longwood Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Longwood vacation 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
$137 nightly
The price is $153
Nov 30 - Dec 1
Total with taxes and fees
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.
$242 nightly
The price is $269
Nov 18 - Nov 19
Total with taxes and fees
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.
$1,479 nightly
The price is $1,648
Nov 10 - Nov 11
Total with taxes and fees
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, (70 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
$218 nightly
The price is $243
Nov 10 - Nov 11
Total with taxes and fees
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.
$202 nightly
The price is $224
Nov 11 - Nov 12
Total with taxes and fees
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A swimming pool with lounge chairs and palm trees.

6. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,495 reviews)
"This is a great place to stay"
United States
Susan
$83 nightly
The price is $93
Nov 23 - Nov 24
Total with taxes and fees
The Point Hotel & Suites Orlando
A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

7. 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
$68 nightly
The price is $76
Nov 23 - Nov 24
Total with taxes and fees
Suites by The Wellborn
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

The View Hotel, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very good, (2,228 reviews)
"Great stay Large comfortable.room Reasonable price"
United States
Martyn
$84 nightly
The price is $95
Nov 22 - Nov 23
Total with taxes and fees
The View Hotel, Trademark Collection by Wyndham
A modern kitchen with a marble countertop, gold faucets, and a large window.

9. 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
$145 nightly
The price is $162
Nov 11 - Nov 12
Total with taxes and fees
Bella Breeze
A modern kitchen with a central island, built-in appliances, and a skylight.

10. Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (110 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
$289 nightly
The price is $323
Nov 10 - Nov 11
Total with taxes and fees
Stylish Boutique Guest house in Winter Park
A backyard with a hammock, outdoor seating, and string lights.

11. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (10 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
$143 nightly
The price is $160
Dec 6 - Dec 7
Total with taxes and fees
The Jazz Loft
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

12. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$150 nightly
The price is $168
Dec 4 - Dec 5
Total with taxes and fees
Boho Nights
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

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.
$116 nightly
The price is $129
Nov 12 - Nov 13
Total with taxes and fees
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
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, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
$215 nightly
The price is $241
Nov 15 - Nov 16
Total with taxes and fees
The Front Porch
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

Villatel Resort Orlando, Apartments by Marriott Bonvoy
4.0 star property
Orlando
9.4 out of 10, Exceptional, (253 reviews)
"This place was great!"
United States
Christine
$324 nightly
The price is $364
Nov 29 - Nov 30
Total with taxes and fees
Villatel Resort Orlando, Apartments by Marriott Bonvoy
A poolside area with lounge chairs, a fire pit, and a building in the background.

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

Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
3.5 star property
International Drive District
9.2 out of 10, Wonderful, (284 reviews)
"Excelente"
United States
Eyda
$181 nightly
The price is $203
Dec 1 - Dec 2
Total with taxes and fees
Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
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.
$217 nightly
The price is $243
Nov 10 - Nov 11
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
IMG 8991

18. 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
$158 nightly
The price is $169
Nov 15 - Nov 16
Total with taxes and fees
The Blue Aztec
A spacious lobby with a wooden floor, seating areas, and a reception desk.

19. 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 traveler
$53 nightly
The price is $59
Nov 10 - Nov 11
Total with taxes and fees
King Bed|Smoking|Orlando
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!

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
College Park
10.0 out of 10, Exceptional, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
$277 nightly
The price is $310
Nov 10 - Nov 11
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando 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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Find vacation rentals that suit your style

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Top Longwood Hotel Reviews

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

La Quinta Inn & Suites by Wyndham Orlando Lake Mary

La Quinta Inn & Suites by Wyndham Orlando Lake Mary
Lake Mary

10/10 Excellent

Great
United States
Patrick
Reviewed October 3, 2024
La Quinta Inn & Suites by Wyndham Orlando Lake Mary

Find out more about Longwood

Everything you need to know about Longwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Longwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Longwood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Longwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $58 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Longwood rentals

At Expedia, we put the best Longwood vacation 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 vacation.

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 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 32 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 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 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.

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