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Longwood Vacation Rentals

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Our top choices for Longwood vacation rentals

3.5 star property
9.2 out of 10, Wonderful, (2357)
"Great location and staff!"
United States
Laura
$221 nightly
The price is $249
Jan 9 - Jan 10, 2026
Total with taxes and fees
Florida Hotel & Conference Center in the Florida Mall

Aparthotel in Florida Center

The Point by Edge
4.0 star property
8.4 out of 10, Very Good, (833)
"It was great really recommend this place"
United States
Sharam
$71 nightly
The price is $80
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Point by Edge
3.0 star property
8.4 out of 10, Very Good, (1490)
"Good sized room, nice staff, good breakfast "
United States
Catherine
$90 nightly
The price is $101
Jan 20 - Jan 21, 2026
Total with taxes and fees
The View Studio Suites and Event Venue

Condo resort in International Drive District

Premium Condos near Universal Studios
3.5 star property
9.2 out of 10, Wonderful, (25)
"Awesome place. "
United States
Ryan
$156 nightly
The price is $176
Jan 20 - Jan 21, 2026
Total with taxes and fees
Premium Condos near Universal Studios
3.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
United States
Anonymous traveler
$284 nightly
The price is $316
Jan 5 - Jan 6, 2026
Total with taxes and fees
Deltona Lake House, Day Trip to Disney & Universal

Cottage in Mount Dora

Historic Tremain Cottages
3.0 star property
8.6 out of 10, Excellent, (34)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
$218 nightly
The price is $242
Jan 8 - Jan 9, 2026
Total with taxes and fees
Historic Tremain Cottages
3.5 star property
8.8 out of 10, Excellent, (183)
"Nice place, comfortable. "
United States
John
$400 nightly
The price is $450
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vista Cay Resort by Casiola Vacation Homes

Apartment in Sanford

Bella Breeze
2.5 star property
9.6 out of 10, Exceptional, (5)
"The place was clean, cozy, and well decorated, and the amenities were wonderful! The hosts have done a great job here."
United States
Courteny
$150 nightly
The price is $168
Jan 6 - Jan 7, 2026
Total with taxes and fees
Bella Breeze

Apartment in Sanford

The Front Porch
3.0 star property
10.0 out of 10, Exceptional, (2)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
$215 nightly
The price is $241
Jan 19 - Jan 20, 2026
Total with taxes and fees
The Front Porch

Apartment in Sanford

Boho Nights
3.0 star property
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
$142 nightly
The price is $159
Jan 18 - Jan 19, 2026
Total with taxes and fees
Boho Nights

Apartment in Florida Center

Century Millenia
3.0 star property
9.0 out of 10, Wonderful, (104)
"Beautiful place to stay and loved that it had washer and dryer on site. Super helpful for a longer stay. Definitely recommend staying here! "
United States
Collin
$191 nightly
The price is $206
Jan 1 - Jan 2, 2026
Total with taxes and fees
Century Millenia

Apartment in Sanford

The Blue Aztec
3.0 star property
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
$224 nightly
The price is $242
Jan 19 - Jan 20, 2026
Total with taxes and fees
The Blue Aztec

Apartment in Sanford

The Jazz Loft
3.0 star property
8.0 out of 10, Very Good, (6)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
$140 nightly
The price is $157
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Jazz Loft

Apartment in Sanford

Totally 80's
3.0 star property
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
$140 nightly
The price is $157
Jan 19 - Jan 20, 2026
Total with taxes and fees
Totally 80's

Condo resort in Florida Center

Premier Resort Condos Near Universal
3.0 star property
9.0 out of 10, Wonderful, (4)
"Great"
United States
Russell
$170 nightly
The price is $192
Jan 4 - Jan 5, 2026
Total with taxes and fees
Premier Resort Condos Near Universal
3.5 star property
9.2 out of 10, Wonderful, (50)
"Its amazing really luxury and comfortable. "
United States
Miguel
$404 nightly
The price is $431
Jan 2 - Jan 3, 2026
Total with taxes and fees
Executive 3 Br Villa @Universal / Vista Cay/Conv.Center

Apartment in International Drive District

Chic Apartment Near Universal w Pool & Hot Tub
3.0 star property
$133 nightly
The price is $150
Jan 12 - Jan 13, 2026
Total with taxes and fees
Chic Apartment Near Universal w Pool & Hot Tub

Apartment in International Drive District

Enclave Swanky
4.0 star property
6.0 out of 10, (2)
"Clean, comfortable, but compact and looking worn / tired. Price point was right."
United Kingdom
Matthew
$367 nightly
The price is $405
Jan 1 - Jan 2, 2026
Total with taxes and fees
Enclave Swanky

Apartment in International Drive District

Studio With Hot Tub Pool Near Universal Studios
2.0 star property
$168 nightly
The price is $189
Dec 30 - Dec 31
Total with taxes and fees
Studio With Hot Tub Pool Near Universal Studios

Apartment in Sanford

The Contemporary
3.0 star property
$285 nightly
The price is $310
Dec 30 - Dec 31
Total with taxes and fees
The Contemporary
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

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 $80 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?

Vista Cay Resort by Casiola Vacation Homes: Located near Longwood, this vacation home rental is located on a lake and has a private balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Longwood?

With 29 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.