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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Longwood vacation rentals

Private kitchen

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
$146 nightly
The price is $161
Aug 19 - Aug 20
Total with taxes and fees
The Longwood Escape • Modern Private Guesthouse Near Orlando
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
7.4 out of 10, Good, (3 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.
$1,607 nightly
The price is $1,776
Aug 11 - Aug 12
Total with taxes and fees
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
Outdoor pool

3. Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (63 reviews)
"Everything was great as usual!!"
United States
Christine B.
$243 nightly
The price is $268
Aug 15 - Aug 16
Total with taxes and fees
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Smart TV, fireplace, video games

4. Early Check In Lake Mary Last-Minute Deal!

Early Check In Lake Mary Last-Minute Deal!
Lake Mary
10.0 out of 10, Exceptional, (20 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$210 nightly
The price is $233
Aug 17 - Aug 18
Total with taxes and fees
Early Check In Lake Mary Last-Minute Deal!
Property grounds

5. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
$341 nightly
The price is $377
Aug 23 - Aug 24
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Coffee/tea maker, fridge, microwave, oven

6. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (44 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
$294 nightly
The price is $325
Aug 23 - Aug 24
Total with taxes and fees
Florida Vacation with pool fun for families
3 bedrooms, desk, iron/ironing board, WiFi (free)

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, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
$224 nightly
The price is $248
Aug 11 - Aug 12
Total with taxes and fees
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Coffee/tea maker, fridge, microwave, paper towels

8. Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Sanford
10.0 out of 10, Exceptional, (8 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.
$109 nightly
The price is $120
Aug 12 - Aug 13
Total with taxes and fees
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Interior

9. Totally 80's

Totally 80's
3.0 star property
Sanford
8.6 out of 10, Excellent, (11 reviews)
"Super cute property and fantastic hosts!!"
United States
Angi
$127 nightly
The price is $142
Aug 21 - Aug 22
Total with taxes and fees
Totally 80's
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

10. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$143 nightly
The price is $160
Aug 18 - Aug 19
Total with taxes and fees
Boho Nights
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

11. 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
$202 nightly
The price is $217
Aug 16 - Aug 17
Total with taxes and fees
The Blue Aztec
Exterior

12. 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
$133 nightly
The price is $149
Aug 12 - Aug 13
Total with taxes and fees
The Jazz Loft
Interior

13. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (20 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
Aug 14 - Aug 15
Total with taxes and fees
Bella Breeze
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
$235 nightly
The price is $261
Aug 11 - Aug 12
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Terrace/patio

15. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
$150 nightly
The price is $158
Aug 11 - Aug 12
Total with taxes and fees
The Blue Aztec
Dining

16. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (20 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
$193 nightly
The price is $213
Aug 17 - Aug 18
Total with taxes and fees
River City Retreat
3 bedrooms, desk, iron/ironing board, WiFi

17. 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 home! My friends and I had such an amazing time and I loved the dog bed & bowls for my dog Venus who stayed with us"
United States
Janelle G.
$334 nightly
The price is $369
Aug 11 - Aug 12
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
1 bedroom, desk, iron/ironing board, WiFi (free)

18. Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.8 out of 10, Exceptional, (16 reviews)
"Just what we needed for our quick trip to Orlando! super communicative host and very nice area. Would love to stay here again if given the chance!"
United States
Liv B.
$158 nightly
The price is $175
Aug 11 - Aug 12
Total with taxes and fees
Yania's Cozy Getaway
2 bedrooms, desk, WiFi (free)

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
$192 nightly
The price is $215
Aug 11 - Aug 12
Total with taxes and fees
The Front Porch
1 bedroom, desk, iron/ironing board, WiFi (free)

20. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (62 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
$119 nightly
The price is $132
Aug 11 - Aug 12
Total with taxes and fees
Private guest studio in the heart of 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

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

10/10 Excellent
"Rooms were clean and well kept, the staff were friendly and always willing to answer questions. All in all it was a great place to stay, close to universal studios and to a lot of local restaurants."
Harry 3-night trip
Posted less than an hour ago
Spark by Hilton Orlando near Universal

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 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 30 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 Spring Hammock Preserve 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.