Winter Springs Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Winter Springs holiday rentals

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Pinnacle Apartments W Amenties by Heavenly Homes

Pinnacle Apartments W Amenties by Heavenly Homes
4.0 star property
Orlando
The price is HK$473
HK$2,411 total
includes taxes & fees
14 May - 15 May
Pinnacle Apartments W Amenties by Heavenly Homes
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (67 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
The price is HK$669
HK$1,257 total
includes taxes & fees
16 May - 17 May
Tiny Hidden Cottage
1 bedroom, desk, WiFi, bed sheets

Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is HK$372
HK$1,233 total
includes taxes & fees
18 May - 19 May
Studio in the heart of Orlando
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
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$879
HK$1,642 total
includes taxes & fees
18 May - 19 May
The Front Porch
Living area

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is HK$593
HK$1,777 total
includes taxes & fees
1 Jun - 2 Jun
The Blue Aztec
Smart TV

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.6 out of 10, Exceptional, (18 reviews)
"Great stay! "
United States
Ash L.
The price is HK$655
HK$1,158 total
includes taxes & fees
17 May - 18 May
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Interior

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very good, (10 reviews)
"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$515
HK$1,103 total
includes taxes & fees
26 May - 27 May
Totally 80's
Outdoor pool

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (52 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is HK$705
HK$1,838 total
includes taxes & fees
27 May - 28 May
“Best Stay Ever” – Recent Guest
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
8.8 out of 10, Excellent, (25 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
The price is HK$501
HK$1,161 total
includes taxes & fees
1 Jun - 2 Jun
The Cozy Crash Pad: Tiny House Experience
1 bedroom, desk, iron/ironing board, free WiFi

Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (58 reviews)
"The guest studio was really good; good facilities, clean and tidy and with lovely little touches in the bathroom. "
United Kingdom
Rebecca
The price is HK$550
HK$1,084 total
includes taxes & fees
18 May - 19 May
Private guest studio in the heart of orlando.
2 bedrooms, iron/ironing board, WiFi, bed sheets

King Bed - Fire Pit - Private - Grill - Location

King Bed - Fire Pit - Private - Grill - Location
Orlando
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed stay met purpose "
United States
Lane R.
The price is HK$658
HK$2,104 total
includes taxes & fees
14 May - 15 May
King Bed - Fire Pit - Private - Grill - Location
Pool

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (22 reviews)
"Great stay in Orlando"
United States
Eddie T.
The price is HK$861
HK$2,157 total
includes taxes & fees
14 May - 15 May
Spacious & Private Guest Pool House Oasis
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Southchase
9.8 out of 10, Exceptional, (27 reviews)
"Everything was amazing described how it was owners were super sweet and loving we were happy to find this place to stay "
United States
Pamela Y.
The price is HK$564
HK$1,011 total
includes taxes & fees
25 May - 26 May
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
1 bedroom, desk, iron/ironing board, free WiFi

Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside
Casselberry
9.4 out of 10, Exceptional, (10 reviews)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
The price is HK$528
HK$1,099 total
includes taxes & fees
20 May - 21 May
Traveler's Dream: Refresh & Recharge Poolside
Interior

Suite Near Universal Studios w Pool & Hot Tub

Suite Near Universal Studios w Pool & Hot Tub
3.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"The room was clean and service was great!"
United States
Daija
The price is HK$448
HK$1,200 total
includes taxes & fees
21 May - 22 May
Suite Near Universal Studios w Pool & Hot Tub
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is HK$881
HK$2,599 total
includes taxes & fees
15 May - 16 May
Incredible Private Lakefront Cottage Retreat
1 bedroom, desk, iron/ironing board, free WiFi

Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.6 out of 10, Exceptional, (15 reviews)
"Very quiet and clean. Great place to relax."
United States
Anonymous traveller
The price is HK$528
HK$1,368 total
includes taxes & fees
18 May - 19 May
Yania's Cozy Getaway
Fridge, microwave, oven, stovetop

Home Sweet Home

Home Sweet Home
Sanford
9.2 out of 10, Wonderful, (29 reviews)
"Beautifully decorated house, super clean and had everything we needed. Stocked well to make everything easy. Great communication from the owner. Checkout process super easy and not stressful. Highly recommend. "
United States
Beth W.
The price is HK$690
HK$2,602 total
includes taxes & fees
18 May - 19 May
Home Sweet Home
Exterior

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.6 out of 10, Excellent, (8 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
The price is HK$564
HK$1,157 total
includes taxes & fees
24 May - 25 May
The Jazz Loft
Living area

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location very clean awesome decor "
United States
Heather
The price is HK$538
HK$1,129 total
includes taxes & fees
26 May - 27 May
Boho Nights
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

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport

8/10 Good
"Pretty good stay overall would come back for sure"
Rahmel 4-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Orlando Airport

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?

Magical Stay Near Universal Studios Florida: This holiday home rental outside of Winter Springs is equipped with a garden, air conditioning and free WiFi to help you feel comfortable during your stay.

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.