Winter Springs Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winter Springs vacation rentals

A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

1. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (344 reviews)
"The check in process was smooth and did not require any front desk it was perfect for a quick stay! The room was pretty big for the price! and very clean. The property itself was cute and cozy they had a very cool common area! Love this stay"
United States
Dustin
The price is NT$2,513
NT$2,827 total
includes taxes & fees
Nov 23 - Nov 24
Suites by The Wellborn
A backyard with a hammock, outdoor seating, and string lights.

2. 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
The price is NT$2,661
NT$5,188 total
includes taxes & fees
Nov 22 - Nov 23
The Jazz Loft
A modern kitchen with a marble countertop, gold faucets, and a large window.

3. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (23 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
The price is NT$2,365
NT$4,857 total
includes taxes & fees
Nov 15 - Nov 16
Bella Breeze
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

4. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is NT$2,661
NT$5,188 total
includes taxes & fees
Dec 4 - Dec 5
Boho Nights
A swimming pool with lounge chairs and palm trees.

5. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,491 reviews)
"This is a great place to stay"
United States
Susan
The price is NT$2,011
NT$2,668 total
includes taxes & fees
Nov 22 - Nov 23
The Point Hotel & Suites Orlando
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.

6. 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
The price is NT$4,139
NT$7,396 total
includes taxes & fees
Nov 15 - Nov 16
The Front Porch
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

7. The View Hotel, Trademark Collection by Wyndham

The View Hotel, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very good, (2,225 reviews)
"Great stay Large comfortable.room Reasonable price"
United States
Martyn
The price is NT$2,765
NT$3,110 total
includes taxes & fees
Nov 22 - Nov 23
The View Hotel, Trademark Collection by Wyndham
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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Find vacation rentals that suit your style

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Top Winter Springs Hotel Reviews

A modern dining area with multiple tables and chairs, large windows, and a wooden accent wall with artwork.
Comfort Inn & Suites Orlando Sanford Airport

Comfort Inn & Suites Orlando Sanford Airport

Comfort Inn & Suites Orlando Sanford Airport
Sanford

10/10 Excellent

The staff was absolutely wonderful
United States
Patricia
Reviewed November 7, 2026
Comfort Inn & Suites Orlando Sanford Airport

Find out more about Winter Springs

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

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

Frequently Asked Questions

Can I find vacation rentals in Winter Springs?

Yes, we give you a choice of vacation rentals near popular attractions in Winter Springs, or you can select a more secluded option if you're looking for a relaxing stay. Winter Springs is known for its temples and breweries. Make sure you have time to check out the baseball games and lake views during your trip.

How many vacation rentals are there in Winter Springs?

Expedia has 9 vacation rentals for your stay in Winter Springs.

What’s there to see and do in Winter Springs?

Boombah-Soldiers Creek Park and Central Winds Park are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places like Universal Orlando Resort and Kia Center.

What’s a vacation rental in Winter Springs like?

A vacation rental is a private property where you can stay for a couple of days or more in Winter Springs. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.