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Compare Vacation Homes in Winter Springs with updated reviews, rates, and availability.

Pool
Spacious & Private Guest Pool House Oasis
10.0 out of 10, Exceptional, (2)
"We enjoyed our stay! Best low key spot to stay at super close to everything very private and the pool was beautiful highly recommend staying here if I ever come back to orlando I will be back !! ❤️"
The price is $100
$266 total
includes taxes & fees
May 22 - May 23
Spacious & Private Guest Pool House Oasis
Interior
Beautiful home close to Parks
10.0 out of 10, Exceptional, (2)
"Myself and a few friends needed a place to stay for a concert in Orlando. This place worked out great. Centrally located and easily accommodated 3 adults. House was as described and was perfect for our needs."
Beautiful home close to Parks
Fridge, microwave, oven, stovetop
Casa Bella
10.0 out of 10, Exceptional, (129)
"Great location, lots of room and enjoyed having the pool at our doorstep"
Casa Bella
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Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
10.0 out of 10, Exceptional, (6)
"ENJOYABLE STAY - CENTRAL LOCATION FOR EXPLORING THE AREA!"
The price is $140
$240 total
includes taxes & fees
May 28 - May 29
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Sport court
Spacious Poolside Home --- 5 min from manatee swimming hole
10.0 out of 10, Exceptional, (5)
"Home was exactly as described in listing. Manager was quick to respond to any questions we had. Home was in a great location, convenient to many state parks, beaches and restaurants. It was in a great location for a central Florida vacation. It was close to Blue Springs, Wekiwa Springs and Rock Springs at Kelly Park. We also took day trips to Kennedy Space Center, Cocoa Beach and Canaveral National Seashore. We are a family of 8 including 3 teenagers and grandparents. The home was a great layout...
Spacious Poolside Home --- 5 min from manatee swimming hole
Paper towels
Cute new townhome, 3bd 2.5 ba, Peloton/weights, printer, bike trail, gated
10.0 out of 10, Exceptional, (3)
"This was by far the best place I have ever stayed in. The house was very clean, the decorations made it feel very homey and the convenience of the place made it perfect for our stay! Both of my brothers live with in walking distance and it couldn’t have worked out any better. I will for sure be staying here again! Thank you for having us, we had the best experience! ❤️"
The price is $231
$477 total
includes taxes & fees
May 27 - May 28
Cute new townhome, 3bd 2.5 ba, Peloton/weights, printer, bike trail, gated
Property grounds
Alluring 2bd/2ba in East Orlando.
10.0 out of 10, Exceptional, (2)
"Had a great stay while visiting for college tours. Property was clean and amenities were very nice. Would recommend for a weekend getaway with friends."
Alluring 2bd/2ba in East Orlando.
Fridge, microwave, oven, stovetop
Renovated Peaceful Luxury Walk to Mall Park Publix
10.0 out of 10, Exceptional, (1)
"We really enjoyed our time here. The porch was really nice to sit out on and it was in a perfect location. Super bathroom and tv size is massive!!"
The price is $99
$215 total
includes taxes & fees
Jun 7 - Jun 8
Renovated Peaceful Luxury Walk to Mall Park Publix
Fridge, microwave, oven, stovetop
near UCF, Valencia, full sail, 417, 408, airport and middle of O' town.
10.0 out of 10, Exceptional, (1)
"Very clean property in a nice neighborhood. Close to UCF and restaurants. The beds were very comfortable. We didn't stay long but the kitchen is well equipped if you plan for longer stays,there is Publix nearby that you have to drive to.On the other hand, it was easy to communicate with the host. "
The price is $129
$252 total
includes taxes & fees
May 26 - May 27
near UCF, Valencia, full sail, 417, 408, airport and middle of O' town.
Property grounds
Infinity pool Luxury furnishings 48 amp level 2 E.V. charger
10.0 out of 10, Exceptional, (6)
"Beautiful and clean, will be my first option next time, thanks 😊"
Infinity pool Luxury furnishings 48 amp level 2 E.V. charger
Pool
Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, (95)
"Pasamos unos dias incredibles y el lugar y la zona muy tranquila ,se los recomiendo"
The price is $90
$200 total
includes taxes & fees
May 28 - May 29
Quiet Oasis in Lovely Neighborhood
Outdoor pool, a heated pool
Near Universal, Disney & OCC Vista Cay town home
9.8 out of 10, Exceptional, (18)
"Very nice place to stay near the parks."
Near Universal, Disney & OCC Vista Cay town home
Fridge, microwave, oven, stovetop
Casa Winter Park
9.8 out of 10, Exceptional, (90)
"We stayed at Casa Winter House for the weekend and had a wonderful time. The house is fully equipped to have a very comfortable stay. There is plenty of parking space and the backyard is huge and perfect for entertaining the family. The host provided all necessary information, we didn’t have to call at all. Absolutely recommend!"
Casa Winter Park
Property grounds
Canterbury Carriage House- private space
9.8 out of 10, Exceptional, (17)
"Second time I have stayed. Clean, beautiful location (across from golf course) responsive owner."
Canterbury Carriage House- private space
Property grounds
The View - Waterfront Tiny Home
9.8 out of 10, Exceptional, (6)
"Was excited to stay at this location when I found the listing at Vrbo but once I arrived, I was blown away. It’s not called The View for nothing."
The price is $116
$213 total
includes taxes & fees
Jun 9 - Jun 10
The View - Waterfront Tiny Home
Smart TV
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
9.6 out of 10, Exceptional, (66)
"The place was fine except there was NO shampoo and NO body wash in either bathroom. We did not realize this until we took morning showers. They were WATER showers only. Very disappointed! The floor in the shared bathroom was grimy. Other than that, we were fine with the place. Thank you."
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Interior
Ocean Guest House !
9.6 out of 10, Exceptional, (43)
"A great no-frills, clean and quiet apartment adjacent to a home in low-traffic suburban neighborhood. Very close to food, shops, Winter Park, and Orlando."
The price is $60
$154 total
includes taxes & fees
May 22 - May 23
Ocean Guest House !
Fridge, microwave, oven, stovetop
Completely Updated Sparkling Town Home in Vista Cay, Must See!
9.6 out of 10, Exceptional, (110)
"This was a beautiful townhouse. It was clean and spacious. The location was perfect for our trip to Universal Studios. Having the pool and other amenities was a bonus. Anthony was great to work with and responded quickly. We would definitely stay there again!"
Completely Updated Sparkling Town Home in Vista Cay, Must See!
Pool
The Ultimate Lakeside Getaway!
9.6 out of 10, Exceptional, (4)
"Great for entertaining indoor & out. Didn’t get to use kayaks or fishing poles due to rain but available. Quiet neighborhood within easy drive of Orlando & surrounding attractions. . Only negative was soap available at a couple at a couple bathrooms but not kitchen or all bathrooms so would bring soap & extra towels. Would recommend."
The Ultimate Lakeside Getaway!
Fridge, microwave, oven, stovetop
Modern 4 Bed 2 Bath home with a pool, King bed sleeps 10 in Orlando close to UCF
9.6 out of 10, Exceptional, (5)
"This home was perfect for what we needed. The living room is very spacious with an open floor plan that leads to the kitchen and dining room area. The kids LOVED the backyard pool. Pool towels, shower towels and hand towels are available; however, you to have to bring your own face rags if you want them. Everything else we needed was there. The kitchen has very nice and modern appliances. We were only in town for a few days but everything we needed was within a few minutes drive. We will...
Modern 4 Bed 2 Bath home with a pool, King bed sleeps 10 in Orlando close to UCF
Don't see what you're looking for?
See all available properties in Winter Springs
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.

Other property types in Winter Springs

Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4834)
"We came in early from our cruise and asked if we could check in early. It was REALLY early. Without hesitation the front desk guy said “of course”. We were able to bring our suitcases to our room and were able to take our son to Universal Studios for the first time as a family. If we weren’t able to do that we wouldn’t have been able to go there. It was amazing. Thank you Hyatt. "
The price is $189
$213 total
includes taxes & fees
May 29 - May 30
Hyatt Regency Orlando International Airport
Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2080)
"Friendly and attentive staff 5 stars "
The price is $76
$102 total
includes taxes & fees
May 23 - May 24
Avanti International Resort
Water park
CoCo Key Hotel and Water Resort 
3.5 star property
7.4 out of 10, Good, (3740)
"Check in super easy and fast. "
The price is $73
$128 total
includes taxes & fees
May 27 - May 28
CoCo Key Hotel and Water Resort 
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.

Winter Springs Vacation Homes information

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