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

Longwood Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Longwood vacation rentals

A living room with a brown sofa, a ceiling fan, and wall art depicting cityscapes and beaches.

1. Longwood Pool Escape | Fire Pit & Sunny Patio

Longwood Pool Escape | Fire Pit & Sunny Patio
Longwood
$283 nightly
The price is $313
Oct 12 - Oct 13
Total with taxes and fees
Longwood Pool Escape | Fire Pit & Sunny Patio
Terrace/patio

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
8.4 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.
$1,592 nightly
The price is $1,761
Oct 11 - Oct 12
Total with taxes and fees
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
A modern kitchen with a microwave, coffee maker, and potted plants. There is a seating area with a sofa and a coffee table.

3. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
$146 nightly
The price is $161
Oct 20 - Oct 21
Total with taxes and fees
The Longwood Escape • Modern Private Guesthouse Near Orlando
A swimming pool with a unique light display creating patterns on the water's surface.

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, (67 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
$222 nightly
The price is $246
Oct 13 - Oct 14
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Private kitchen

5. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (48 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
$305 nightly
The price is $337
Oct 19 - Oct 20
Total with taxes and fees
Florida Vacation with pool fun for families
A modern kitchen with white cabinets, a microwave, and a green wall with a neon sign.

6. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$201 nightly
The price is $222
Oct 15 - Oct 16
Total with taxes and fees
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

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, (58 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
$222 nightly
The price is $246
Oct 12 - Oct 13
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.

8. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,398 reviews)
"Enjoyed our stay and felt it was a great price for the location."
United States
Lisa
$81 nightly
The price is $91
Nov 10 - Nov 11
Total with taxes and fees
The Point Hotel & Suites Orlando
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

9. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (336 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
$77 nightly
The price is $86
Oct 26 - Oct 27
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.

10. 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, (2,180 reviews)
"Everything was amazing. Easy check in and check out, great location and quiet place. Breakfast was great and the food was excellent excellent."
United States
Breila
$82 nightly
The price is $92
Oct 18 - Oct 19
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.

11. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (21 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
$140 nightly
The price is $157
Oct 11 - Oct 12
Total with taxes and fees
Bella Breeze
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
Oct 12 - Oct 13
Total with taxes and fees
Boho Nights
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

13. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"The house was perfect for our three night stay. The location was a short distance to all our activities. It was super clean and had very nice updates. The area was quiet and the house very comfortable. If we are in the area again, we’ll definitely stay there again!"
United States
Janice M.
$282 nightly
The price is $312
Oct 19 - Oct 20
Total with taxes and fees
Home Sweet Home
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

14. 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.
$232 nightly
The price is $258
Oct 11 - Oct 12
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

15. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
$207 nightly
The price is $232
Oct 11 - Oct 12
Total with taxes and fees
The Blue Aztec
A backyard with a hammock, outdoor seating, and string lights.

16. 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
$130 nightly
The price is $146
Oct 11 - Oct 12
Total with taxes and fees
The Jazz Loft
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

17. 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.
$127 nightly
The price is $140
Oct 11 - Oct 12
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.

18. 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
$225 nightly
The price is $252
Oct 11 - Oct 12
Total with taxes and fees
The Front Porch
IMG 8991

19. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
$160 nightly
The price is $170
Oct 11 - Oct 12
Total with taxes and fees
The Blue Aztec
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

20. 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
$332 nightly
The price is $367
Oct 12 - Oct 13
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longwood Hotel Reviews

Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

8/10 Good
"Had some issues with the humidity getting in the room, but otherwise had a good experience. Breakfast was more options than traditional continental breakfast and we used the free shuttle to universal"
Eve 5-night trip
Posted less than an hour ago
Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

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 $91 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.

Explore a world of travel with Expedia

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.