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Winter Springs Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter Springs holiday rentals

A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

1. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is S$196
includes taxes & fees
1 Oct - 2 Oct
Cozy Modern Studio
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

2. 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 S$189
includes taxes & fees
27 Sept - 28 Sept
Boho Nights
A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

3. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
The price is S$291
includes taxes & fees
24 Sept - 25 Sept
The Blue Aztec
A modern kitchen with a marble countertop, gold faucets, and a large window.

4. 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 S$195
includes taxes & fees
28 Sept - 29 Sept
Bella Breeze
A backyard with a hammock, outdoor seating, and string lights.

5. 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 S$189
includes taxes & fees
1 Oct - 2 Oct
The Jazz Loft
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 S$287
includes taxes & fees
30 Sept - 1 Oct
The Front Porch
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 S$278
includes taxes & fees
27 Sept - 28 Sept
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 price is S$351
includes taxes & fees
26 Sept - 27 Sept
The Contemporary
A modern kitchen with a central island, bar stools, and a dining area with a sofa and table.

9. 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 S$504
includes taxes & fees
28 Sept - 29 Sept
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
A dining room with a round wooden table set for six, surrounded by wooden chairs. A chandelier hangs from the ceiling, and a wooden cabinet with glass doors is to the right.

10. Upstay 2BR Golfer s Retreat w Patio Ventura Resort

Upstay 2BR Golfer s Retreat w Patio Ventura Resort
2.0 star property
Ventura
The price is S$315
includes taxes & fees
19 Oct - 20 Oct
Upstay 2BR Golfer s Retreat w Patio Ventura Resort
A spacious living room with a beige sofa, a television, and a balcony with a view of the outdoors.

11. 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 S$306
includes taxes & fees
19 Oct - 20 Oct
Upstay Golfer's Retreat w Patio at Ventura Resort
A modern bedroom with a bed, a ceiling fan, and a TV on the wall.

12. 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 S$477
includes taxes & fees
26 Sept - 27 Sept
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

13. 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
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
A modern living room with a glass dining table, black upholstered chairs, a black sofa with decorative pillows, and a black and gold patterned rug.

14. Sunny Stays

Sunny Stays
2.0 star property
Oak Ridge
The price is S$359
includes taxes & fees
24 Sept - 25 Sept
Sunny Stays
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.

15. Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (148 reviews)
"Absolutely amazing and perfect will be back here everytime!"
United States
Arianna
The price is S$259
includes taxes & fees
1 Oct - 2 Oct
Century Millenia
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

16. 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, (2,156 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 S$118
includes taxes & fees
30 Sept - 1 Oct
The View Hotel, Trademark Collection by Wyndham
A swimming pool with lounge chairs and palm trees.

17. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,326 reviews)
"Clean rooms, friendly staff, and great location."
United States
Lianet
The price is S$110
includes taxes & fees
7 Oct - 8 Oct
The Point Hotel & Suites Orlando

18. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is S$717
includes taxes & fees
24 Sept - 25 Sept
Rustic Hideaway - Great Location + Pet Friendly!
A swimming pool with lounge chairs, palm trees, and a building with multiple floors in the background.

19. Cozy 1BR Condo w Pool - Near Universal Studios

Cozy 1BR Condo w Pool - Near Universal Studios
3.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
The price is S$191
includes taxes & fees
28 Sept - 29 Sept
Cozy 1BR Condo w Pool - Near Universal Studios
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

20. 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 S$625
includes taxes & fees
30 Sept - 1 Oct
Luxury House - Sleeps 8 Golf Disney Family Fun
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

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Great hotel"
Carlos 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport

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.

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.