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Longwood Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Longwood holiday rentals

Reception
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
Orlando
9.2 out of 10, Wonderful, (2357)
"Great location and staff!"
United States
Laura
Florida Hotel & Conference Center in the Florida Mall
Terrace/patio
The Point by Edge

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very good, (833)
"It was great really recommend this place"
United States
Sharam
The price is S$89
includes taxes & fees
7 Jan - 8 Jan, 2026
The Point by Edge
Restaurant
The View Studio Suites and Event Venue

The View Studio Suites and Event Venue

The View Studio Suites and Event Venue
3.0 star property
Orlando
8.4 out of 10, Very good, (1490)
"Good sized room, nice staff, good breakfast "
United States
Catherine
The price is S$123
includes taxes & fees
28 Dec - 29 Dec
The View Studio Suites and Event Venue
Front of property
Premium Condos near Universal Studios

Premium Condos near Universal Studios

Premium Condos near Universal Studios
3.5 star property
International Drive District
9.2 out of 10, Wonderful, (25)
"Awesome place. "
United States
Ryan
The price is S$236
includes taxes & fees
6 Jan - 7 Jan, 2026
Premium Condos near Universal Studios
Interior
Deltona Lake House, Day Trip to Disney & Universal

Deltona Lake House, Day Trip to Disney & Universal

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
Deltona Lakes
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 traveller
The price is S$406
includes taxes & fees
5 Jan - 6 Jan, 2026
Deltona Lake House, Day Trip to Disney & Universal
Terrace/patio
Historic Tremain Cottages

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
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
Historic Tremain Cottages
Fountain
Vista Cay Resort by Casiola Vacation Homes

Vista Cay Resort by Casiola Vacation Homes

Vista Cay Resort by Casiola Vacation Homes
3.5 star property
Orlando
8.8 out of 10, Excellent, (183)
"Nice place, comfortable. "
United States
John
The price is S$550
includes taxes & fees
6 Jan - 7 Jan, 2026
Vista Cay Resort by Casiola Vacation Homes
Interior
Bella Breeze

Bella Breeze

Bella Breeze
2.5 star property
Sanford
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
Bella Breeze
2 bedrooms, desk, free WiFi
The Front Porch

The Front Porch

The Front Porch
3.0 star property
Sanford
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
The Front Porch
Living area
Boho Nights

Boho Nights

Boho Nights
3.0 star property
Sanford
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Private kitchen
Century Millenia

Century Millenia

Century Millenia
3.0 star property
Florida Center
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
Century Millenia
Living area
The Blue Aztec

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Exterior
The Jazz Loft

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
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
The Jazz Loft
Interior
Totally 80's

Totally 80's

Totally 80's
3.0 star property
Sanford
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
The price is S$201
includes taxes & fees
19 Jan - 20 Jan, 2026
Totally 80's
Bar (on property)
Premier Resort Condos Near Universal

Premier Resort Condos Near Universal

Premier Resort Condos Near Universal
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (4)
"Great"
United States
Russell
The price is S$237
includes taxes & fees
4 Jan - 5 Jan, 2026
Premier Resort Condos Near Universal
Courtyard
Executive 3 Br Villa @Universal / Vista Cay/Conv.Center

Executive 3 Br Villa @Universal / Vista Cay/Conv.Center

Executive 3 Br Villa @Universal / Vista Cay/Conv.Center
3.5 star property
Orlando
9.2 out of 10, Wonderful, (50)
"Its amazing really luxury and comfortable. "
United States
Miguel
The price is S$515
includes taxes & fees
3 Jan - 4 Jan, 2026
Executive 3 Br Villa @Universal / Vista Cay/Conv.Center
Interior
Chic Apartment Near Universal w Pool & Hot Tub

Chic Apartment Near Universal w Pool & Hot Tub

Chic Apartment Near Universal w Pool & Hot Tub
3.0 star property
International Drive District
The price is S$188
includes taxes & fees
12 Jan - 13 Jan, 2026
Chic Apartment Near Universal w Pool & Hot Tub
Interior
Enclave Swanky

Enclave Swanky

Enclave Swanky
4.0 star property
International Drive District
6.0 out of 10, (2)
"Clean, comfortable, but compact and looking worn / tired. Price point was right."
United Kingdom
Matthew
The price is S$540
includes taxes & fees
1 Jan - 2 Jan, 2026
Enclave Swanky
Internet
Studio With Hot Tub Pool Near Universal Studios

Studio With Hot Tub Pool Near Universal Studios

Studio With Hot Tub Pool Near Universal Studios
2.0 star property
International Drive District
Studio With Hot Tub Pool Near Universal Studios
Exterior
The Contemporary

The Contemporary

The Contemporary
3.0 star property
Sanford
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

CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

10/10 Excellent
"Swimming pool was cleaned and enjoyable. Staff were very friendly and warming. I really loved this place. My kids enjoyed every single thing. "
Marianna 1-night trip
Posted 1 day ago
CoCo Key Hotel and Water Resort 

Frequently asked questions

Can I find holiday rentals in Longwood?

Yes, there are holiday rentals close to the most popular sights in Longwood, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Longwood has to offer?

Vista Cay Resort by Casiola Vacation Homes: This holiday home rental outside of Longwood is located on a lake, and has a private balcony, a terrace and a BBQ 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/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Longwood?

With 29 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Longwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longwood. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.