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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 1586 Vacation Homes in Winter Springs with updated reviews, rates, and availability.

Quiet Oasis in Lovely Neighborhood
Pool

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (131)
"We had an amazing stay here and wished we could have stayed longer, everything was perfect and we are so grateful."
The price is AED 331
AED 693 total
includes taxes & fees
29 Apr - 30 Apr
Quiet Oasis in Lovely Neighborhood
Vista Cay Resort by Casiola Vacation Homes
3 outdoor pools, a heated pool, pool umbrellas, sun loungers

Vista Cay Resort by Casiola Vacation Homes

3.5 star property
8.8 out of 10, Excellent, (177)
"I loved my stay at the Vista Cay Resort by Casiola Vacation Homes. It’s so quiet, so clean. Definitely I will stay there again They exceeded my expectations "
The price is AED 616
AED 1,573 total
includes taxes & fees
7 May - 8 May
Vista Cay Resort by Casiola Vacation Homes
The Cozy Crash Pad: Tiny House Experience
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

9.6 out of 10, Exceptional, (17)
"Overall, charming and cozy with nice deck and rain shower. "
The price is AED 235
AED 545 total
includes taxes & fees
4 May - 5 May
The Cozy Crash Pad: Tiny House Experience
Donwtown Orlando Thornton Park Historic District - Heated Salt Pool Hot Tub
Outdoor pool, a heated pool

Donwtown Orlando Thornton Park Historic District - Heated Salt Pool Hot Tub

8.2 out of 10, Very Good, (60)
"I used to live in this beautiful area and it was such a treat to be able to stay somewhere right in the middle of all that is historic downtown Orlando. It is such a unique and beautiful neighborhood and NOTHING like other areas of the city--but you have to experience it to understand that. Dyna's spot is smack in the midst of it, and just a few minute's walk to the little bars, bistros and quaint places to gather, including Lake Eola. She is a lovely person and we could not have enjoyed staying...
Donwtown Orlando Thornton Park Historic District - Heated Salt Pool Hot Tub
Orlando Modern Spacious Home Near Universal
Fridge, microwave, oven, stovetop

Orlando Modern Spacious Home Near Universal

9.2 out of 10, Wonderful, (47)
"The house was everything excepted beds were comfortable the house was well cleaned will definitely be staying again the neighborhood was quite and clean the house was conveniently located close to all stores and restaurants "
Orlando Modern Spacious Home Near Universal
THE CHLOE by EVRH
Terrace/patio

THE CHLOE by EVRH

9.0 out of 10, Wonderful, (57)
"Overall great. No major complaints. Anything that I could “complain” about would be minor cosmetic upgrades - nothing that actually impacted my stay. Definitely staying here again. "
The price is AED 437
AED 1,867 total
includes taxes & fees
28 Apr - 29 Apr
THE CHLOE by EVRH
Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Fridge, microwave, oven, stovetop

Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views

9.0 out of 10, Wonderful, (67)
"Great location too our gymnastics venue. Something for everyone to do at the house. Just know the pool is not heated, that was the only downfall for us. Other than that we had amazing time at the home"
The price is AED 889
AED 2,182 total
includes taxes & fees
20 May - 21 May
Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Fridge, microwave, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (23)
"Property was located in a quiet neighborhood, that was safe and well kept. Enjoyed the peace and quiet. "
The price is AED 533
AED 1,010 total
includes taxes & fees
28 Apr - 29 Apr
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Pool

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

8.8 out of 10, Excellent, (89)
"We had an incredible stay at this beautiful home! From the moment we arrived, everything felt warm, welcoming, and perfectly set up for a relaxing getaway. The house was spotless, thoughtfully decorated, and stocked with everything we needed and more. The hosts clearly care about their guests’ comfort—every detail was well thought out, from cozy linens to a fully equipped kitchen. The location was perfect, and we really appreciated the peaceful atmosphere. It truly felt like a “mi casa es su...
The price is AED 474
AED 1,702 total
includes taxes & fees
28 Apr - 29 Apr
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Private Luxury Pool / Smart-home
A heated pool

Private Luxury Pool / Smart-home

9.6 out of 10, Exceptional, (65)
"This is a great property! Its location put us very close to everything we were doing (Universal, Kia Center, and restaurants). The pool is great! My only suggestion is to leave a list of things to do each day for pool maintenance (empty the filter basket, empty the vacuum baskets, etc) so that the leaves don’t overwhelm the pool. I figured it out as I went and it was fine, but if you aren’t familiar with pool care like me, it takes a little bit of investigation. Overall, great home,...
Private Luxury Pool / Smart-home
Blocks a way to Universal Studios. Full Single Family with pool, and amenities.
Outdoor pool

Blocks a way to Universal Studios. Full Single Family with pool, and amenities.

7.6 out of 10, Good, (4)
"Everything was perfect and clean, very spacious and comfortable, walked in to a welcome basket! Great people and property overall."
The price is AED 287
AED 1,088 total
includes taxes & fees
10 May - 11 May
Blocks a way to Universal Studios. Full Single Family with pool, and amenities.
Waterside. Pet friendly. UCF area.
Exterior

Waterside. Pet friendly. UCF area.

9.6 out of 10, Exceptional, (133)
"This our second time booking this property. Both times everything was as expected. Vicky always replied promptly to any e-mails. We would definitely stay here again!"
Waterside. Pet friendly. UCF area.
Casa Winter Park
Outdoor pool

Casa Winter Park

9.8 out of 10, Exceptional, (108)
"Was great"
Casa Winter Park
Cozy House in Orlando w Large Yard 20m to Downtown
Terrace/patio

Cozy House in Orlando w Large Yard 20m to Downtown

10.0 out of 10, Exceptional, (2)
"for me, it was excellent. I want to be close to Orlando executive airport for some flight training. Location was spot on facilities were great. The only thing I could say is that they should maybe clean the exterior windows, but the interior was spotless. All equipment worked except the oven which they knew the previous renter had broken the glass, but otherwise everything was A-OK"
The price is AED 433
AED 933 total
includes taxes & fees
28 Apr - 29 Apr
Cozy House in Orlando w Large Yard 20m to Downtown
Beautiful home close to Parks
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
THE OLIVIA by EVRH
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

THE OLIVIA by EVRH

8.6 out of 10, Excellent, (31)
"Did the job and was a sweet place to stay. Quiet neighborhood and close to the springs "
The price is AED 400
AED 1,716 total
includes taxes & fees
28 Apr - 29 Apr
THE OLIVIA by EVRH
Casa Bella
Fridge, microwave, oven, stovetop

Casa Bella

9.8 out of 10, Exceptional, (150)
"Lovely home--clean, spacious. The kitchen was very, very well stocked. "
Casa Bella
Lake Marion Apt w/ Canoe in Altamonte Springs!
Fridge, microwave, stovetop, dishwasher

Lake Marion Apt w/ Canoe in Altamonte Springs!

9.8 out of 10, Exceptional, (77)
"If you just want to chill out by the lake , R&R this is you place. They had fishing poles, chairs, umbrella, a beautiful wrap around porch where bought some wine and we hung out and played scrabble. The apartment was charming with all amenities and comforts. Amazing hosts! Choose how to spend your day, shopping, a mall, movie theater, all restaurants everything is close by. We will definitely be returning. 5 stars "
Lake Marion Apt w/ Canoe in Altamonte Springs!
Apopka Single-Story Home w/ Private Lanai + Pool!
Fridge, microwave, stovetop, dishwasher

Apopka Single-Story Home w/ Private Lanai + Pool!

9.6 out of 10, Exceptional, (37)
"Great area close to everything. Home was equipped with everything we needed. Thank you for letting us into your home."
Apopka Single-Story Home w/ Private Lanai + Pool!
Spacious Poolside Home --- 5 min from manatee swimming hole
Outdoor pool, a heated pool

Spacious Poolside Home --- 5 min from manatee swimming hole

9.8 out of 10, Exceptional, (19)
"The pool was heated and clean. Nice patio area and we enjoyed swimming everyday. Comfortable furniture in the home with plenty of sleeping room available. Multiple TVs available. Fully stocked kitchen. Snacks and bottled water greeted us. Quiet residential area. Easy to get to stores, restaurants and attractions. We enjoyed our stay! "
Spacious Poolside Home --- 5 min from manatee swimming hole
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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Other property types in Winter Springs

The View Studio Suites and Event Venue
Exterior

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (1033)
"Amazing"
The price is AED 252
AED 284 total
includes taxes & fees
1 May - 2 May
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1888)
"Beautiful property. The location was perfect for us. Love that the mall was right there so we had plenty of food options. Rooms were clean and the bed was comfortable."
The price is AED 639
AED 814 total
includes taxes & fees
10 May - 11 May
Florida Hotel & Conference Center in the Florida Mall
Sonder Vista Cay
Outdoor pool

Sonder Vista Cay

3.5 star property
9.0 out of 10, Wonderful, (197)
"Apartment was clean. "
The price is AED 477
AED 536 total
includes taxes & fees
25 May - 26 May
Sonder Vista Cay
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.