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Winter Springs Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winter Springs vacation rentals

A swimming pool with a unique light display creating patterns on the water's surface.

1. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (68 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is ￥17,632
￥42,162 total
includes taxes & fees
Nov 4 - Nov 5
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

2. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (58 reviews)
"This home was just what we needed, it was clean and comfortable. Great communication with the owner. Nice, safe neighborhood."
United States
Angie P.
The price is ￥20,453
￥39,272 total
includes taxes & fees
Nov 2 - Nov 3
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A white cabinet with a built-in fireplace, wooden flooring, and a shelf with decorative items.

3. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is ￥14,811
￥38,532 total
includes taxes & fees
Nov 2 - Nov 3
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A bedroom with a bed, bedside table, lamp, chair, and a small round table with a chair.

4. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (341 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 ￥12,000
￥13,499 total
includes taxes & fees
Oct 28 - Oct 29
Suites by The Wellborn
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

5. Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Sanford
9.8 out of 10, Exceptional, (9 reviews)
"Perfect spot for a quick night after your flight into Sanford. Close to the airport, clean accommodations in a quiet neighborhood. Couldn’t ask for more!"
United States
Julia F.
The price is ￥18,040
￥23,342 total
includes taxes & fees
Oct 26 - Oct 27
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A backyard with a hammock, outdoor seating, and string lights.

6. 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 ￥12,695
￥24,751 total
includes taxes & fees
Nov 8 - Nov 9
The Jazz Loft
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

7. Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.6 out of 10, Exceptional, (13 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is ￥16,457
￥40,535 total
includes taxes & fees
Oct 26 - Oct 27
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
A modern kitchen with a marble countertop, gold faucets, and a large window.

8. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (22 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 ￥10,580
￥22,382 total
includes taxes & fees
Oct 25 - Oct 26
Bella Breeze
A swimming pool with lounge chairs and palm trees.

9. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,442 reviews)
"Convenient to parks and good value."
United States
Tracy
The price is ￥9,593
￥12,732 total
includes taxes & fees
Nov 9 - Nov 10
The Point Hotel & Suites Orlando
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

10. 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
The price is ￥18,337
￥57,212 total
includes taxes & fees
Oct 25 - Oct 26
Tranquil 3-bedroom house in Sanford with AC, WiFi
IMG 8991

11. 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
The price is ￥14,118
￥28,362 total
includes taxes & fees
Oct 25 - Oct 26
The Blue Aztec
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

12. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (16 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥10,658
￥28,350 total
includes taxes & fees
Oct 27 - Oct 28
Downtown Cottage
A modern kitchen with a central island, built-in appliances, and a skylight.

13. Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (110 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
The price is ￥23,531
￥54,494 total
includes taxes & fees
Oct 26 - Oct 27
Stylish Boutique Guest house in Winter Park
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

14. 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, (2,200 reviews)
"Excellent hotel and service in my first time in this hotel."
United States
Oscar
The price is ￥12,424
￥13,978 total
includes taxes & fees
Nov 22 - Nov 23
The View Hotel, Trademark Collection by Wyndham
A modern kitchen with grey cabinets, a wooden countertop, and a built-in stove.

15. Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
10.0 out of 10, Exceptional, (15 reviews)
"Clean and quiet spot with an easy check-in process. Super close to the lake with lots of restaurants within walking distance. Parking was easy to access and made getting in and out quite easy."
United States
Caroline V.
The price is ￥11,436
￥25,532 total
includes taxes & fees
Oct 26 - Oct 27
Lake Eola view 1 bedroom Thornton Park
A bedroom with a tufted headboard, striped pillows, a bed with a blue blanket, a gray rug, and a white closet with louvered doors.

16. Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.4 out of 10, Exceptional, (25 reviews)
"Good place"
United States
Rodrigo
The price is ￥9,169
￥23,148 total
includes taxes & fees
Oct 26 - Oct 27
Beautiful Studio near Int. Drive, Disney & Airport.
A spacious lobby with a kitchen area, seating arrangements, and a view of the outdoors.

17. 2 Full Beds Non-Smoking

2 Full Beds Non-Smoking
Orlando FL
9.6 out of 10, Exceptional, (30 reviews)
"The staff were friendly and helpful during check in."
United States
Anonymous traveler
The price is ￥7,946
￥10,432 total
includes taxes & fees
Oct 25 - Oct 26
2 Full Beds Non-Smoking
A modern house with a garage, a well-maintained lawn, and decorative lighting along the pathway.

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

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (39 reviews)
"Awesome place to stay! Clean as a whistle, and nice and private! "
United States
N T.
The price is ￥13,747
￥31,979 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Private Apartment - Stylish & Spotless — No sharing areas
A bedroom with a bed, a ceiling fan, a stained glass window, and a door leading to another room.

19. TINY unit in cottage in the middle of Downtown

TINY unit in cottage in the middle of Downtown
Downtown Orlando
9.8 out of 10, Exceptional, (23 reviews)
"The unit was nice and clean. It was a close walk to the Kia Center. In a pretty quiet area."
United States
Paula
The price is ￥9,310
￥23,129 total
includes taxes & fees
Nov 16 - Nov 17
TINY unit in cottage in the middle of Downtown
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
The price is ￥24,262
￥40,340 total
includes taxes & fees
Oct 26 - Oct 27
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 Winter Springs Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"We enjoyed every moment. Coming back next year."
Carolina 5-night trip
Posted 4 hours ago
Universal's Cabana Bay Beach Resort

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:

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

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.

What are some of the best vacation home rentals that Winter Springs has to offer?

Salt Pool, cozy House near Downtown and International Airport: Visitors like this Winter Springs vacation home rental. It 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 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.