Winter Springs Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Winter Springs vacation 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 CA $99
CA $439 total
includes taxes & fees
May 10 - May 11
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 CA $102
CA $203 total
includes taxes & fees
May 11 - May 12
Tiny Hidden 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 CA $65
CA $215 total
includes taxes & fees
May 12 - May 13
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 CA $154
CA $288 total
includes taxes & fees
Jun 9 - Jun 10
The Front Porch
Standard Apartment | 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 CA $105
CA $312 total
includes taxes & fees
May 17 - May 18
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 CA $108
CA $195 total
includes taxes & fees
May 12 - May 13
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 CA $92
CA $195 total
includes taxes & fees
May 10 - May 11
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 CA $137
CA $346 total
includes taxes & fees
May 27 - May 28
“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 CA $87
CA $203 total
includes taxes & fees
May 25 - May 26
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 CA $96
CA $189 total
includes taxes & fees
May 11 - May 12
Private guest studio in the heart of orlando.
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 CA $115
CA $371 total
includes taxes & fees
May 11 - May 12
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 CA $150
CA $382 total
includes taxes & fees
May 12 - May 13
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 CA $98
CA $176 total
includes taxes & fees
May 21 - May 22
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
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 CA $92
CA $192 total
includes taxes & fees
May 11 - May 12
Traveler's Dream: Refresh & Recharge Poolside
Apartment (1 Bedroom) | 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 CA $77
CA $208 total
includes taxes & fees
May 12 - May 13
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 CA $154
CA $451 total
includes taxes & fees
May 10 - May 11
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 CA $92
CA $239 total
includes taxes & fees
May 12 - May 13
Yania's Cozy Getaway
Fridge, microwave, oven, stovetop

Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (28 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 CA $113
CA $453 total
includes taxes & fees
May 12 - May 13
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 CA $98
CA $202 total
includes taxes & fees
May 12 - May 13
The Jazz Loft
Standard Apartment | Living area

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
The price is CA $96
CA $199 total
includes taxes & fees
May 25 - May 26
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

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

10/10 Excellent
"The breakfast was great they only served waffles on the weekends. Also the staff was pleasant the room was clean and the ac kept the room cooldddd. Overall it was a great experience an I’ll definitely be back. "
L Amanda 6-night trip
Posted 2 hours ago
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

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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: You might want to consider this vacation home rental near Winter Springs, which is equipped with a garden, air-conditioning, and free WiFi 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 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.