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Longwood Vacation Rentals

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Check prices for these dates

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Longwood vacation rentals

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, (834)
"Awesome and clean place to stay for the holidays"
United States
Moses
The price is P3,384
P4,534 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Point by Edge
Lobby sitting area
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, (1505)
"Good sized room, nice staff, good breakfast "
United States
Catherine
The price is P5,023
P5,651 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The View Studio Suites and Event Venue
1 bedroom
Peaceful 1 King BR Apartment w Hot Tub & Pool

Peaceful 1 King BR Apartment w Hot Tub & Pool

Peaceful 1 King BR Apartment w Hot Tub & Pool
2.0 star property
International Drive District
The price is P3,878
P9,845 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Peaceful 1 King BR Apartment w Hot Tub & Pool
Exterior
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
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 P4,700
P9,212 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Totally 80's
Terrace/patio
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
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
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
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

DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown

10/10 Excellent
"Everything was spot on! Donna at the front desk was extremely delightful! Thanks for the cookies 😊"
Rhonshea 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Orlando Downtown

Find out more about Longwood

Search for holiday rentals in Longwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Longwood using one of the methods below:

  • View our selection of featured holiday rentals in Longwood
  • Use the map to find apartments and other holiday homes in the Longwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Longwood while they last

Look no further and take a look at our great range of rental properties in Longwood!

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.

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.