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Winter Springs Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winter Springs vacation 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 P4,591
P9,866 total
includes taxes & fees
Oct 30 - Oct 31
Cozy Modern Studio
A modern kitchen with a marble countertop, gold faucets, and a large window.

2. 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 P5,385
P10,263 total
includes taxes & fees
Nov 17 - Nov 18
Bella Breeze
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.

3. 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 P11,236
P17,881 total
includes taxes & fees
Oct 19 - Oct 20
The Front Porch
A backyard with a hammock, outdoor seating, and string lights.

4. 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 P5,107
P9,957 total
includes taxes & fees
Nov 8 - Nov 9
The Jazz Loft
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

5. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (337 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 P4,818
P5,420 total
includes taxes & fees
Oct 26 - Oct 27
Suites by The Wellborn
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.

6. 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 Mellow Yellow
A modern kitchen with a central island, bar stools, and a dining area with a sofa and table.

7. 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 P6,944
P25,336 total
includes taxes & fees
Oct 21 - Oct 22
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
A swimming pool with lounge chairs and palm trees.

8. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,423 reviews)
"Convenient to parks and good value."
United States
Tracy
The price is P3,621
P4,854 total
includes taxes & fees
Nov 11 - Nov 12
The Point Hotel & Suites Orlando
A modern bedroom with a bed, a ceiling fan, and a TV on the wall.

9. 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 P18,196
P24,775 total
includes taxes & fees
Oct 30 - Oct 31
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
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
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
Upstay Golfer's Retreat w Patio at Ventura Resort
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

12. 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, (2,187 reviews)
"Excellent hotel and service in my first time in this hotel."
United States
Oscar
The price is P5,175
P5,822 total
includes taxes & fees
Oct 28 - Oct 29
The View Hotel, Trademark Collection by Wyndham
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
The price is P6,384
P17,822 total
includes taxes & fees
Oct 21 - Oct 22
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.

14. Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (155 reviews)
"Easy booking. Great price. When I arrived the code wasn't working so I called in and got a new code quickly and easily. The unit was beautiful, clean, comfortable and fully stocked with necessities. The onsite laundry machines was a bonus while traveling."
United States
Jessica
The price is P6,428
P11,960 total
includes taxes & fees
Nov 4 - Nov 5
Century Millenia
A swimming pool with a water slide, surrounded by palm trees and lounge chairs.

15. 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, (244 reviews)
"Good place to stay."
United States
Geronimo
The price is P32,624
P39,890 total
includes taxes & fees
Oct 27 - Oct 28
Villatel Resort Orlando, Apartments by Marriott Bonvoy
A modern multi-story residential building with balconies, a gated entrance, and a well-maintained garden.

16. Sunny Stays

Sunny Stays
2.0 star property
Oak Ridge
The price is P6,802
P17,729 total
includes taxes & fees
Oct 18 - Oct 19
Sunny Stays
A patio with Adirondack chairs and a round table, surrounded by palm trees and a brick floor.

17. 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, (281 reviews)
"Everything was good"
United States
Ghansham
The price is P9,527
P12,134 total
includes taxes & fees
Nov 16 - Nov 17
Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
A high-rise hotel with a swimming pool surrounded by greenery, located near a body of water and a parking lot.

18. Premium Condos near Universal Studios

Premium Condos near Universal Studios
4.0 star property
International Drive District
9.2 out of 10, Wonderful, (74 reviews)
"Property was well clean, and well managed. Very easy to report to your room no hassle at all. And plenty of parking."
United States
Lee
The price is P4,483
P9,229 total
includes taxes & fees
Nov 2 - Nov 3
Premium Condos near Universal Studios
A modern hotel lobby with a pool table, seating area, and a staircase.

19. Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe

Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe
4.0 star property
International Drive District
The price is P6,566
P14,944 total
includes taxes & fees
Oct 21 - Oct 22
Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe
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
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

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

8/10 Good
"Room is clean and staff is helpful and friendly."
Charissa 3-night trip
Posted 2 hours ago
Spark by Hilton Orlando near Universal

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.