Winter Springs Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Winter Springs vacation rentals

Outdoor pool

Orlando Pool, WiFi, Clean, Cozy King size bed and outdoor patio

Orlando Pool, WiFi, Clean, Cozy King size bed and outdoor patio
Lake Mary
9.6 out of 10, Exceptional, (50 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is ￥17,898
￥42,638 total
includes taxes & fees
Apr 15 - Apr 16
Orlando Pool, WiFi, Clean, Cozy King size bed and outdoor patio
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 ￥18,614
￥34,212 total
includes taxes & fees
Apr 19 - Apr 20
The Front Porch
Outdoor dining

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 ￥10,751
￥22,363 total
includes taxes & fees
Apr 13 - Apr 14
Traveler's Dream: Refresh & Recharge Poolside
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (65 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
The price is ￥11,324
￥23,005 total
includes taxes & fees
Apr 12 - Apr 13
Tiny Hidden Cottage
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Boho Nights
3.0 star property
Sanford
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
The price is ￥11,454
￥23,519 total
includes taxes & fees
Apr 19 - Apr 20
Boho Nights
1 bedroom, desk, iron/ironing board, free WiFi

Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.6 out of 10, Exceptional, (14 reviews)
"Very quiet and clean. Great place to relax."
United States
Anonymous traveler
The price is ￥10,739
￥27,792 total
includes taxes & fees
Apr 13 - Apr 14
Yania's Cozy Getaway
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

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 ￥11,897
￥35,973 total
includes taxes & fees
May 4 - May 5
The Blue Aztec
Smart TV, fireplace, video games

Relax Tonight. Cozy, Quiet and Super Clean.

Relax Tonight. Cozy, Quiet and Super Clean.
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"An excellent location for stays in Lake Mary. It has everything a single or a couple needs to feel at home."
United States
Kanzeda C.
The price is ￥15,051
￥38,679 total
includes taxes & fees
Apr 12 - Apr 13
Relax Tonight. Cozy, Quiet and Super Clean.
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very Good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥9,307
￥27,076 total
includes taxes & fees
Apr 16 - Apr 17
Downtown Cottage
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 ￥7,569
￥25,089 total
includes taxes & fees
Apr 12 - Apr 13
Studio in the heart of Orlando
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 ￥17,500
￥42,875 total
includes taxes & fees
Apr 18 - Apr 19
Spacious & Private Guest Pool House Oasis
2 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Great host, and stayed connected with us."
United States
Christopher
The price is ￥16,704
￥39,872 total
includes taxes & fees
Apr 18 - Apr 19
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Exterior

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.4 out of 10, Very Good, (7 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 ￥11,454
￥23,519 total
includes taxes & fees
Apr 19 - Apr 20
The Jazz Loft
Exterior detail

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (31 reviews)
"Awesome place to stay! Clean as a whistle, and nice and private! "
United States
N T.
The price is ￥13,523
￥29,135 total
includes taxes & fees
Apr 13 - Apr 14
Cozy Private Apartment - Stylish & Spotless — No sharing areas
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
9.0 out of 10, Wonderful, (24 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
The price is ￥10,193
￥23,611 total
includes taxes & fees
Apr 13 - Apr 14
The Cozy Crash Pad: Tiny House Experience
1 bedroom, iron/ironing board, 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, (24 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 ￥11,467
￥20,566 total
includes taxes & fees
Apr 12 - Apr 13
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Interior

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Geneva
9.4 out of 10, Exceptional, (19 reviews)
"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 ￥15,432
￥26,702 total
includes taxes & fees
Apr 14 - Apr 15
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Smart TV

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.4 out of 10, Exceptional, (15 reviews)
"Great stay! "
United States
Ash L.
The price is ￥14,191
￥24,526 total
includes taxes & fees
Apr 22 - Apr 23
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, (9 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 ￥10,750
￥22,743 total
includes taxes & fees
May 5 - May 6
Totally 80's
Living area

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 ￥13,364
￥41,483 total
includes taxes & fees
Apr 12 - Apr 13
King Bed - Fire Pit - Private - Grill - Location
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Everything was great. Just long lines"
Kathy 3-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal 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 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.

What are some of the best vacation home rentals that Winter Springs has to offer?

Magical Stay Near Universal Studios Florida: Visitors like this Winter Springs vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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 Lake Jesup 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.