Winter Springs Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Winter Springs holiday rentals

Terrace/patio
The Point by Edge

Aparthotel in Florida Center

The Point by Edge
4.0 star property
8.4 out of 10, Very good, (831)
"The staff was friendly, hotel was so beautiful "
United States
Aaronda
The price is HK$476
HK$632 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Point by Edge
Interior
Tiny house in Orlando

Apartment in Orlando

Tiny house in Orlando
9.6 out of 10, Exceptional, (7)
"The women was very nice and the space was really cozy, and clean. It was close to stores and other places i really liked it"
United States
Jasper
The price is HK$171
HK$887 total
includes taxes & fees
20 Dec - 21 Dec
Tiny house in Orlando
Fridge, microwave, oven, stovetop
“NATURE IN THE CITY”

Mobile Home in Union Park

“NATURE IN THE CITY”
2.0 star property
9.0 out of 10, Wonderful, (6)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
The price is HK$595
HK$1,724 total
includes taxes & fees
19 Dec - 20 Dec
“NATURE IN THE CITY”
Restaurant
The View Studio Suites and Event Venue

Aparthotel in Orlando

The View Studio Suites and Event Venue
3.0 star property
8.4 out of 10, Very good, (1473)
"Good staff Good location "
Canada
Maryon
The price is HK$665
HK$748 total
includes taxes & fees
21 Dec - 22 Dec
The View Studio Suites and Event Venue
Living area
The Blue Aztec

Apartment in Sanford

The Blue Aztec
3.0 star property
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Interior
Totally 80's

Apartment in Sanford

Totally 80's
3.0 star property
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is HK$622
HK$1,220 total
includes taxes & fees
19 Dec - 20 Dec
Totally 80's
Interior
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Mobile Home in Geneva

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
9.6 out of 10, Exceptional, (16)
"This place was perfect for me and my dad and my son to stay at while my son played ball close by."
United States
Kevin D.
The price is HK$794
HK$1,349 total
includes taxes & fees
16 Jan - 17 Jan 2026
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Reception
Florida Hotel & Conference Center in the Florida Mall

Aparthotel in Orlando

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.2 out of 10, Wonderful, (2335)
"Great location "
United States
Zandra
Florida Hotel & Conference Center in the Florida Mall
Exterior
The Jazz Loft

Apartment in Sanford

The Jazz Loft
3.0 star property
8.0 out of 10, Very good, (6)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
The Jazz Loft
Exterior
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Holiday Home in Orlando

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
8.8 out of 10, Excellent, (100)
"We had a great time at the house! Close to everything, spacious, clean, and with a good host! "
Norway
Synnøve Sætervik H.
The price is HK$755
HK$3,622 total
includes taxes & fees
19 Dec - 20 Dec
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Living area
Boho Nights

Apartment in Sanford

Boho Nights
3.0 star property
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Front of property
Premium Condos near Universal Studios

Condo resort in International Drive District

Premium Condos near Universal Studios
3.5 star property
9.2 out of 10, Wonderful, (25)
"Awesome place. "
United States
Ryan
The price is HK$676
HK$1,277 total
includes taxes & fees
19 Dec - 20 Dec
Premium Condos near Universal Studios
2 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Apartment in Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
10.0 out of 10, Exceptional, (5)
"Great host, and stayed connected with us."
United States
Christopher
The price is HK$576
HK$1,678 total
includes taxes & fees
21 Dec - 22 Dec
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
2 bedrooms, desk, free WiFi
The Front Porch

Apartment in Sanford

The Front Porch
3.0 star property
10.0 out of 10, Exceptional, (2)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
The Front Porch
Exterior detail
Pet Friendly!✰ Charming home with big patio!

Holiday Home in Oviedo

Pet Friendly!✰ Charming home with big patio!
10.0 out of 10, Exceptional, (20)
"Beautiful place to stay, clean and peaceful. Definitely recommend this place "
United States
Yesenia R.
The price is HK$931
HK$2,769 total
includes taxes & fees
19 Dec - 20 Dec
Pet Friendly!✰ Charming home with big patio!
Outdoor dining
Traveler's Dream: Refresh & Recharge Poolside

Apartment in Casselberry

Traveler's Dream: Refresh & Recharge Poolside
2.0 star property
9.4 out of 10, Exceptional, (6)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
The price is HK$560
HK$1,131 total
includes taxes & fees
28 Dec - 29 Dec
Traveler's Dream: Refresh & Recharge Poolside
1 bedroom, desk, iron/ironing board, free WiFi
Private guest studio in the heart of orlando.

Apartment in Orlando

Private guest studio in the heart of orlando.
9.8 out of 10, Exceptional, (54)
"Great place, clean and great neighborhood "
United States
Carlos G.
The price is HK$483
HK$1,006 total
includes taxes & fees
21 Dec - 22 Dec
Private guest studio in the heart of orlando.
Interior
Thornton park paradise 1 bedroom Lake Eola

Apartment in Thornton Park

Thornton park paradise 1 bedroom Lake Eola
2.0 star property
10.0 out of 10, Exceptional, (2)
"Will definitely use this place again "
United States
Tony W.
The price is HK$595
HK$1,263 total
includes taxes & fees
21 Dec - 22 Dec
Thornton park paradise 1 bedroom Lake Eola
Interior
Deltona Lake House, Day Trip to Disney & Universal

Cottage in Deltona Lakes

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
United States
Anonymous traveller
The price is HK$902
HK$2,461 total
includes taxes & fees
22 Dec - 23 Dec
Deltona Lake House, Day Trip to Disney & Universal
Smart TV
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Holiday Home in Deltona

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
9.6 out of 10, Exceptional, (10)
"The space was private, comfortable and very clean. Ashlee is an amazing hostess. "
United States
Belinda M.
The price is HK$609
HK$1,103 total
includes taxes & fees
21 Dec - 22 Dec
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Springs Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Fantastic hotel"
Gabe 8-night trip
Posted 21 hours ago
Rosen Inn at Pointe Orlando

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?

Vista Cay Resort by Casiola Vacation Homes: This holiday home rental outside of Winter Springs is located on a lake, and has a private balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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 Kia Center and Orlando International Premium Outlets.

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.