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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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
$144 nightly
The price is $159
Sep 13 - Sep 14
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
8.0 out of 10, Very Good, (4 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 27 - Aug 28
Total with taxes and fees
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
A bedroom with a bed, a TV on the wall, a dresser, and a framed picture.

3. Brand NewPainted Vacation Hse NrUCF PetsOK Fenced

Brand NewPainted Vacation Hse NrUCF PetsOK Fenced
Orlando
9.6 out of 10, Exceptional, (19 reviews)
"Host was very welcoming and communicative; property was as advertised and suited our needs. "
United States
Jeanie G.
$278 nightly
The price is $293
Aug 28 - Aug 29
Total with taxes and fees
Brand NewPainted Vacation Hse NrUCF PetsOK Fenced
A modern house with a garage, a well-maintained lawn, and decorative lighting along the pathway.

4. Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (36 reviews)
"Awesome place to stay! Clean as a whistle, and nice and private! "
United States
N T.
$168 nightly
The price is $186
Sep 1 - Sep 2
Total with taxes and fees
Cozy Private Apartment - Stylish & Spotless — No sharing areas
A swimming pool with a covered patio area, chairs, and a view of the sunset.

5. Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (28 reviews)
"The pool house looked exactly like the pictures and it was a very comfortable place to stay. My husband and I really enjoyed it and would definitely stay there again in the future."
United States
Dionne T.
$246 nightly
The price is $272
Aug 27 - Aug 28
Total with taxes and fees
Spacious & Private Guest Pool House Oasis
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

6. 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 27 - Aug 28
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
A seating area with wicker chairs and a small table, a wooden wall with shelves holding potted plants, and a striped rug on the floor.

7. The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
8.8 out of 10, Excellent, (28 reviews)
"This place was clean and the bed very comfortable.I tried reaching the host twice and they never replied. For a one night stay the price was high and a hotel probably much more spacious. After one shower we ran out of hot water."
United States
Yira H.
$132 nightly
The price is $146
Sep 1 - Sep 2
Total with taxes and fees
The Cozy Crash Pad: Tiny House Experience
A modern kitchen with a dining area, a black sofa, and a painting of a sunset.

8. Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
10.0 out of 10, Exceptional, (22 reviews)
"Super cute would stay here again"
United States
Kristen a.
$150 nightly
The price is $166
Aug 27 - Aug 28
Total with taxes and fees
Cozy studio in fabulous Orlando close to everything
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

9. 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
Aug 28 - Aug 29
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
A small house with a porch, a red door, and potted plants.

10. The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Lake Helen
9.8 out of 10, Exceptional, (42 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
$126 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A modern living room with a flat-screen TV, a ceiling fan, a dining area with a kitchen in the background, and a hallway leading to another room.

11. A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.6 out of 10, Exceptional, (23 reviews)
"Host was extremely attentive and available whenever we reached out. She was flexible with our arrival as well. The property was clean, cozy and perfect for our needs. "
United States
Kimberly
$134 nightly
The price is $148
Aug 31 - Sep 1
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
A modern hotel room with a bed, white curtains, a small desk with a lamp, a refrigerator, and a microwave.

12. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (64 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 30 - Aug 31
Total with taxes and fees
Private guest studio in the heart of orlando.
A modern kitchen with a marble countertop, gold faucets, and a large window.

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
$136 nightly
The price is $152
Aug 27 - Aug 28
Total with taxes and fees
Bella Breeze

14. 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
Aug 31 - Sep 1
Total with taxes and fees
The Blue Aztec
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
$211 nightly
The price is $227
Aug 31 - Sep 1
Total with taxes and fees
The Blue Aztec
A spacious living room with a ceiling fan, a door, a window with blinds, and a patterned rug.

16. Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (25 reviews)
"Quiet neighborhood, good location."
United States
River
$249 nightly
The price is $276
Aug 28 - Aug 29
Total with taxes and fees
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

17. 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.
$197 nightly
The price is $217
Sep 1 - Sep 2
Total with taxes and fees
River City Retreat
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

18. 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
Aug 30 - Aug 31
Total with taxes and fees
Boho Nights
A backyard with a hammock, outdoor seating, and string lights.

19. 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 1 - Sep 2
Total with taxes and fees
The Jazz Loft
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.

20. 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
$200 nightly
The price is $224
Aug 27 - Aug 28
Total with taxes and fees
The Front Porch
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

Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

10/10 Excellent
"Definitely recommended..."
DEONNA 4-night trip
Posted 1 hour ago
Coco Key Hotel & Water Park Resort

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 $95 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 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 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.