Photo by Stephanie Moraca

Winter Springs Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Browse Select Winter Springs Vacation Homes

Our top choices for Winter Springs vacation homes

Long Term Stays! 2 MI to DT Orlando & Winter Park

2.0 star property
8.0 out of 10, Very good, (4)
"Wonderful location for getting around Winter Park and downtown Orlando; lots of shopping options and so many great food choices. Quaint neighborhood, nice park close by, very quiet! "
Long Term Stays! 2 MI to DT Orlando & Winter Park

Banana Leaf Villa-Vintage Vibes Premium Room

2.0 star property
8.0 out of 10, Very good, (4)
"This is the perfect getaway spot! Very accessible, quiet area. I will definitely be booking again."
The price is CA $119
CA $160 total
includes taxes & fees
Aug 22 - Aug 23
Banana Leaf Villa-Vintage Vibes Premium Room

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

8.8 out of 10, Excellent, (95)
"We had a great time on our family vacation here. The place felt clean and was comfortable. We had a short weekend, but while there we enjoyed our stay. The pool was nice to get into after a long day. Would definitely stay again. "
The price is CA $136
CA $653 total
includes taxes & fees
Aug 24 - Aug 25
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

9.8 out of 10, Exceptional, (7)
"This place is a great size guest suite on a scenic property in a rural area close to the suburbs, very nice getaway, we enjoyed our short stay! It's very clean and cozy, and the hosts are very helpful, thank you!"
The price is CA $131
CA $222 total
includes taxes & fees
Aug 25 - Aug 26
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Tranquil 3-bedroom house in Sanford with AC, WiFi

9.8 out of 10, Exceptional, (17)
"Beautiful place to stay near the airport "
The price is CA $162
CA $331 total
includes taxes & fees
Aug 24 - Aug 25
Tranquil 3-bedroom house in Sanford with AC, WiFi

Home Sweet Home

9.8 out of 10, Exceptional, (18)
"House was clean and in a quiet neighborhood. Was the perfect size for family of 4. "
The price is CA $77
CA $411 total
includes taxes & fees
Aug 24 - Aug 25
Home Sweet Home

Spacious & Private Guest Pool House Oasis

9.6 out of 10, Exceptional, (14)
"Great location , Very enjoy , private space, would book in the future for sure "
The price is CA $146
CA $377 total
includes taxes & fees
Aug 24 - Aug 25
Spacious & Private Guest Pool House Oasis

8-Person Luxury Stay Near Disney World & Attractions

2.0 star property
7.4 out of 10, Good, (3)
"My friend and I enjoyed our stay. The beds were very comfortable and the home was immaculate! Thank you so much for hosting an incredible home."
The price is CA $180
CA $231 total
includes taxes & fees
Aug 22 - Aug 23
8-Person Luxury Stay Near Disney World & Attractions

6-bedroom 3bath "Clue" Themed home near parks

2.0 star property
9.0 out of 10, Wonderful, (9)
"Close to where we need to work."
The price is CA $222
CA $589 total
includes taxes & fees
Sep 2 - Sep 3
6-bedroom 3bath "Clue" Themed home near parks

Comfortable 1 bedroom home

8.8 out of 10, Excellent, (3)
"Host and location were awesome . Nestled in an great neighborhood. Will definitely stay again."
The price is CA $83
CA $244 total
includes taxes & fees
Aug 22 - Aug 23
Comfortable 1 bedroom home

Studio in the heart of Orlando

8.8 out of 10, Excellent, (3)
"Clean room. Comfortable bed. Quiet neighborhood. A nice place to come back to after being out and about all day. There were a few rules that we were not used to seeing, but it could be because it is on the college side of Orlando. Overall, it was good place to stay and served its purpose.served the purpose "
The price is CA $61
CA $214 total
includes taxes & fees
Sep 8 - Sep 9
Studio in the heart of Orlando

Sunshine Escape Guesthouse ☀

9.6 out of 10, Exceptional, (9)
"Great place to stay to get away for the weekend. Quiet neighborhood not far fromPark Ave "
The price is CA $81
CA $220 total
includes taxes & fees
Aug 24 - Aug 25
Sunshine Escape Guesthouse ☀

Charming 2-bedroom apartment in house with AC, WiFi included

10.0 out of 10, Exceptional, (1)
"Very nice place. Very clean. Would stay again"
The price is CA $131
CA $191 total
includes taxes & fees
Aug 23 - Aug 24
Charming 2-bedroom apartment in house with AC, WiFi included

Renovated Peaceful Luxury Walk to Mall Park Publix

9.4 out of 10, Exceptional, (11)
"Very nice little place walking distance to Advent Health."
The price is CA $148
CA $295 total
includes taxes & fees
Aug 24 - Aug 25
Renovated Peaceful Luxury Walk to Mall Park Publix

Vista Cay Resort, Next To Universal 821 3 Bedroom Townhouse

3.0 star property
10.0 out of 10, Exceptional, (1)
"Thank you was nice "
The price is CA $174
CA $790 total
includes taxes & fees
Aug 23 - Aug 24
Vista Cay Resort, Next To Universal 821 3 Bedroom Townhouse

The Cozy Crash Pad: Tiny House Experience

9.2 out of 10, Wonderful, (19)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
The price is CA $80
CA $196 total
includes taxes & fees
Aug 24 - Aug 25
The Cozy Crash Pad: Tiny House Experience

Cozy House in Orlando w/ a Large Fenced Yard 15m to Downtown

9.6 out of 10, Exceptional, (7)
"Nice home and location. "
The price is CA $147
CA $345 total
includes taxes & fees
Sep 1 - Sep 2
Cozy House in Orlando w/ a Large Fenced Yard 15m to Downtown

Modern Tropical Pool Home ⭐️

9.6 out of 10, Exceptional, (18)
"Our family had a great time staying at the house. The kids loved the heated pool in December. They also loved the movie room. We all hung out there together and spent great quality time. "
The price is CA $208
CA $527 total
includes taxes & fees
Aug 28 - Aug 29
Modern Tropical Pool Home ⭐️

Pet Friendly!✰ Charming home with big patio!

10.0 out of 10, Exceptional, (16)
"Beautiful place to stay, clean and peaceful. Definitely recommend this place "
The price is CA $184
CA $520 total
includes taxes & fees
Sep 12 - Sep 13
Pet Friendly!✰ Charming home with big patio!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

10.0 out of 10, Exceptional, (30)
"Great property and host "
The price is CA $181
CA $347 total
includes taxes & fees
Aug 22 - Aug 23
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Springs Hotel Reviews