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

Longwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Longwood vacation 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
$150 nightly
The price is $166
Sep 29 - Sep 30
Total with taxes and fees
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
8.4 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.
$1,595 nightly
The price is $1,764
Sep 26 - Sep 27
Total with taxes and fees
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, Exceptional, (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.
$224 nightly
The price is $248
Sep 29 - Sep 30
Total with taxes and fees
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, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$200 nightly
The price is $221
Sep 28 - Sep 29
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.

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)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
$227 nightly
The price is $251
Sep 28 - Sep 29
Total with taxes and fees
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

6. 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
Sep 27 - Sep 28
Total with taxes and fees
Florida Vacation with pool fun for families
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

7. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$145 nightly
The price is $162
Sep 26 - Sep 27
Total with taxes and fees
Boho Nights
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

8. 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
Sep 27 - Sep 28
Total with taxes and fees
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

9. 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, Exceptional, (7 reviews)
$120 nightly
The price is $133
Sep 27 - Sep 28
Total with taxes and fees
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

10. 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
$212 nightly
The price is $237
Sep 28 - Sep 29
Total with taxes and fees
The Blue Aztec
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
$145 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
Bella Breeze

12. 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
$165 nightly
The price is $175
Sep 28 - Sep 29
Total with taxes and fees
The Blue Aztec
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

13. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"Pet friendly, all you need for a quick trip to Orlando with a couple and their pet"
United States
Jackson K.
$171 nightly
The price is $171
Sep 26 - Sep 27
Total with taxes and fees
CUTE and COZY studio w/ jacuzzi!
A backyard with a hammock, outdoor seating, and string lights.

14. 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
$140 nightly
The price is $157
Sep 26 - Sep 27
Total with taxes and fees
The Jazz Loft
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

15. 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
Sep 27 - Sep 28
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
A waterfront view with a dock, a swan, and modern buildings in the background.

16. NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry

NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
Orlando
9.2 out of 10, Wonderful, (13 reviews)
"The studio is super cute with nice outdoor space. Close to UCF campus, restaurants, and shopping."
United States
Michael
$159 nightly
The price is $168
Sep 28 - Sep 29
Total with taxes and fees
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
A house with a red door, a front porch, and a pathway leading to the entrance.

17. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$159 nightly
The price is $176
Sep 28 - Sep 29
Total with taxes and fees
Downtown Cottage
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

18. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (21 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
$192 nightly
The price is $212
Oct 2 - Oct 3
Total with taxes and fees
River City Retreat
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.

19. 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
Sep 27 - Sep 28
Total with taxes and fees
The Front Porch
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

20. 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.
$222 nightly
The price is $248
Sep 26 - Sep 27
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely 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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Top Longwood Hotel Reviews

Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport

8/10 Good
"Location"
Patrick 6-night trip
Posted 8 hours ago
Ramada by Wyndham Suites Orlando Airport

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 $87 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.