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Winter Springs Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winter Springs holiday rentals

A modern kitchen with a marble countertop, gold faucets, and a large window.

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (21 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 HK$565
HK$1,160 total
includes taxes & fees
4 Oct - 5 Oct
Bella Breeze
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 HK$565
HK$1,160 total
includes taxes & fees
4 Oct - 5 Oct
The Jazz Loft
A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

3. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is HK$572
HK$1,229 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Modern Studio
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 HK$600
HK$1,200 total
includes taxes & fees
2 Oct - 3 Oct
Boho Nights
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.

5. 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 HK$989
HK$1,766 total
includes taxes & fees
2 Oct - 3 Oct
The Front Porch
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

6. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is HK$600
HK$1,788 total
includes taxes & fees
11 Oct - 12 Oct
The Blue Aztec
A compact kitchen with a built-in sink, a countertop, and a grey cabinet. There is a sofa with a cushion and a small table in the adjacent living area.

7. The Mellow Yellow

The Mellow Yellow
3.0 star property
Downtown Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
The price is HK$600
HK$1,788 total
includes taxes & fees
28 Oct - 29 Oct
The Mellow Yellow
A backyard with a hammock, outdoor seating, and a hot tub.

8. The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The Contemporary
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

9. 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, (2,159 reviews)
"Everything was amazing. Easy check in and check out, great location and quiet place. Breakfast was great and the food was excellent excellent."
United States
Breila
The price is HK$634
HK$713 total
includes taxes & fees
1 Nov - 2 Nov
The View Hotel, Trademark Collection by Wyndham
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

10. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (334 reviews)
"Establishment with meticulously designed in, which made it very comfortable. I enjoyed my stay tremendously. The communication of the staff was amazing, our room is immaculate, a bar had a very in fighting comforting environment very clean get place to socialize with friends and family.I will see you next year the same time."
United States
Sondria
The price is HK$600
HK$675 total
includes taxes & fees
4 Oct - 5 Oct
Suites by The Wellborn
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

11. Luxury House - Sleeps 8 Golf Disney Family Fun

Luxury House - Sleeps 8 Golf Disney Family Fun
2.0 star property
Ventura
8.0 out of 10, Very good, (2 reviews)
"Some items like the towel rail was damaged upon arrival other than that the stay was amazing !!"
United States
myron
The price is HK$810
HK$3,787 total
includes taxes & fees
5 Oct - 6 Oct
Luxury House - Sleeps 8 Golf Disney Family Fun
A modern kitchen with a central island, bar stools, and a dining area with a sofa and table.

12. Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
4.0 star property
Downtown Orlando
10.0 out of 10, Exceptional, (1 review)
"Very nice place"
United States
John
The price is HK$818
HK$3,103 total
includes taxes & fees
5 Oct - 6 Oct
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
A swimming pool with lounge chairs and palm trees.

13. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,358 reviews)
"Enjoyed our stay and felt it was a great price for the location."
United States
Lisa
The price is HK$484
HK$642 total
includes taxes & fees
21 Oct - 22 Oct
The Point Hotel & Suites Orlando
A spacious living room with a beige sofa, a television, and a balcony with a view of the outdoors.

14. Upstay Golfer's Retreat w Patio at Ventura Resort

Upstay Golfer's Retreat w Patio at Ventura Resort
3.5 star property
Ventura
The price is HK$643
HK$1,863 total
includes taxes & fees
19 Oct - 20 Oct
Upstay Golfer's Retreat w Patio at Ventura Resort
A modern multi-story residential building with balconies, a gated entrance, and a well-maintained garden.

15. Sunny Stays

Sunny Stays
2.0 star property
Oak Ridge
The price is HK$847
HK$2,209 total
includes taxes & fees
2 Oct - 3 Oct
Sunny Stays
A modern bedroom with a bed, a ceiling fan, and a TV on the wall.

16. Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
3.5 star property
Colonialtown South
The price is HK$2,267
HK$3,087 total
includes taxes & fees
14 Oct - 15 Oct
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
A swimming pool with a water slide, surrounded by palm trees and lounge chairs.

17. Villatel Resort Orlando, Apartments by Marriott Bonvoy

Villatel Resort Orlando, Apartments by Marriott Bonvoy
4.0 star property
Orlando
9.2 out of 10, Wonderful, (237 reviews)
"Had a great stay"
United States
Aristides
The price is HK$5,634
HK$6,735 total
includes taxes & fees
20 Oct - 21 Oct
Villatel Resort Orlando, Apartments by Marriott Bonvoy
A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

18. Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
8.0 out of 10, Very good, (1 review)
"Large 2br apartment with access to a very nice pool and other amenities! Fully equipped kitchen, laundry, 2 full bedrooms and bathrooms, 3 good tvs, screened in balcony. Keep in mind that it is a third floor walk up and be sure to read the guides on check in, especially parking and trash."
United States
Kathy
The price is HK$1,024
HK$2,476 total
includes taxes & fees
26 Oct - 27 Oct
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
A modern kitchen with dark wood cabinets, a granite countertop, and a central island. There is a dining area with a table and chairs, and a view of the outside through large windows.

19. Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (149 reviews)
"Absolutely amazing and perfect will be back here everytime!"
United States
Arianna
The price is HK$892
HK$1,592 total
includes taxes & fees
25 Oct - 26 Oct
Century Millenia
A patio with Adirondack chairs and a round table, surrounded by palm trees and a brick floor.

20. Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort

Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
3.5 star property
International Drive District
9.2 out of 10, Wonderful, (279 reviews)
"Great apartments, perfect for families exploring Universal and the wider Orlando area."
United Kingdom
Niki
The price is HK$1,121
HK$1,438 total
includes taxes & fees
1 Nov - 2 Nov
Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
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

Avanti International Resort

Avanti International Resort

10/10 Excellent
"I had an amazing stay!"
Marcus 2-night trip
Posted less than an hour ago
Avanti International 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 holiday rentals in Winter Springs?

Yes, there are holiday rentals close to the most popular sights 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 holiday rentals that Winter Springs has to offer?

Salt Pool, cozy House near Downtown and International Airport: This holiday home rental outside of Winter Springs is located in the city centre, and has a garden, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Winter Springs?

Expedia has 9 holiday 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 such as Universal Orlando Resort and Kia Center.

What’s a holiday rental in Winter Springs like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winter Springs. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips.