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Winter Springs Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Winter Springs Vacation Homes

Blocks a way to Universal Studios. Full Single Family with pool, and amenities.
Relax by the pool surrounded by lush greenery and a tranquil atmosphere.

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

8.2 out of 10, Very good, (10)
"GREAT STAY"
The price is CA $200
CA $530 total
includes taxes & fees
Sep 2 - Sep 3
Blocks a way to Universal Studios. Full Single Family with pool, and amenities.
Quiet Oasis in Lovely Neighborhood
Swimmers can enjoy a refreshing dip in the rectangular pool, adjacent to a hot tub, with a clear view of the surrounding trees.

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (145)
"Hosts were wondeful. Nice quiet neighborhood. Our favorite part was definitely the pool. "
The price is CA $111
CA $263 total
includes taxes & fees
Aug 11 - Aug 12
Quiet Oasis in Lovely Neighborhood
Luxury Family Retreat • Sleeps 8 • Near Disney World
Enjoy cooking in this well-equipped kitchen with a central island, bar stools, and stainless steel appliances.

Luxury Family Retreat • Sleeps 8 • Near Disney World

8.0 out of 10, Very good, (4)
"We stayed for one night on our way into Disney. "
The price is CA $179
CA $229 total
includes taxes & fees
Aug 11 - Aug 12
Luxury Family Retreat • Sleeps 8 • Near Disney World
Lake House Pets allowed
Relax by the pool surrounded by lush greenery and lounge chairs.

Lake House Pets allowed

9.8 out of 10, Exceptional, (42)
"Amazing property, I highly recommend."
The price is CA $186
CA $495 total
includes taxes & fees
Aug 11 - Aug 12
Lake House Pets allowed
Casa Winter Park
Relax by the pool surrounded by a patio and a gazebo with comfortable seating.

Casa Winter Park

9.8 out of 10, Exceptional, (114)
"Perfect house for a family gathering. Will definitely book again. "
Casa Winter Park
Vista Cay Resort by Casiola Vacation Homes
Relax by the pool surrounded by palm trees and enjoy a refreshing swim or lounge on the sun-kissed deck.

Vista Cay Resort by Casiola Vacation Homes

3.5 star property
8.8 out of 10, Excellent, (181)
"Excellent "
The price is CA $189
CA $541 total
includes taxes & fees
Aug 12 - Aug 13
Vista Cay Resort by Casiola Vacation Homes
The Villa Orlando@College Park. Sleeps16.
Fully equipped kitchen with oven, microwave, and coffee maker.

The Villa Orlando@College Park. Sleeps16.

10.0 out of 10, Exceptional, (11)
"Great location, just as advertised "
The price is CA $343
CA $646 total
includes taxes & fees
Aug 25 - Aug 26
The Villa Orlando@College Park. Sleeps16.
There's space for everyone in this gorgeous 3-Story Townhome near the theme park
Outdoor pool, a heated pool

There's space for everyone in this gorgeous 3-Story Townhome near the theme park

9.8 out of 10, Exceptional, (100)
"Easy check in, clean, comfy, amazing pool and perfect fit for everyone. We will be staying here again "
There's space for everyone in this gorgeous 3-Story Townhome near the theme park
Eastpark. Pet friendly! Lake Nona
Relax in this stylish living room with a large dining table, comfortable sofa, and beautiful artwork.

Eastpark. Pet friendly! Lake Nona

9.2 out of 10, Wonderful, (86)
"The home is as advertised. Beutiful home in a quite neighborhood with a wonderful host."
The price is CA $200
CA $469 total
includes taxes & fees
Aug 11 - Aug 12
Eastpark. Pet friendly! Lake Nona
The Epic Toronto Vista Cay Orlando
Relax by the resort's central pool surrounded by sun loungers and umbrellas, with scenic views of a nearby body of water.

The Epic Toronto Vista Cay Orlando

9.8 out of 10, Exceptional, (6)
"This was a good place to stay and centrally located for work and entertainment."
The Epic Toronto Vista Cay Orlando
Beautiful home close to Parks
Cozy living space with a kitchenette, sofa, and potted plant.

Beautiful home close to Parks

10.0 out of 10, Exceptional, (2)
"Very cute and quiet place to stay! The property manager is super sweet and great with communication! I would certainly stay here again!"
Beautiful home close to Parks
Tiny tropical Orlando Univesal-Disney
Stroll up to this charming home, featuring a cozy porch and lush surroundings.

Tiny tropical Orlando Univesal-Disney

6.0 out of 10, (11)
"Perfect little cottage for our two night stay. Close to all the attractions and shopping, very clean, and my husband loved the upgrades. Fully fenced with lock drive in gate and had TV's in every room. Would definitely stay again. "
Tiny tropical Orlando Univesal-Disney
Charming 4-bedroom house with pool table in BEAUTIFUL Orlando
Relax in this inviting living room with a large sectional sofa, flat-screen TV, and cozy fireplace.

Charming 4-bedroom house with pool table in BEAUTIFUL Orlando

8.0 out of 10, Very good, (4)
"All good "
The price is CA $255
CA $542 total
includes taxes & fees
Aug 31 - Sep 1
Charming 4-bedroom house with pool table in BEAUTIFUL Orlando
Luxury home
Enjoy cooking in this well-equipped kitchen with a central island and bar seating, featuring a refrigerator, microwave, and large window with an outdoor view.

Luxury home

9.6 out of 10, Exceptional, (5)
"Roomy, clean, excellent location."
Luxury home
Swim, Golf & Relax: Lovely Home in Lake Mary
Features a well-lit kitchen with stainless steel appliances, microwave, oven, dishwasher, and sink.

Swim, Golf & Relax: Lovely Home in Lake Mary

9.6 out of 10, Exceptional, (5)
"We stayed here to be close enough to Apopka to visit family , but have plenty of room for ourselves. The host was very easy to communicate with. The host was accommodating and made our stay very pleasant. I enjoyed being able to go outside with my coffee by the pool & the smell of the flowering bush to pool was delightful. I enjoy the convenience of an onsite laundry and a full kitchen.I will stay here again!"
Swim, Golf & Relax: Lovely Home in Lake Mary
Upstay - Home w Garden, BBQ and Games at Golf Club
Enjoy cooking in this well-equipped kitchen with a dishwasher, coffee maker, and ample counter space.

Upstay - Home w Garden, BBQ and Games at Golf Club

8.0 out of 10, Very good, (6)
"Comfortable space to stay. "
Upstay - Home w Garden, BBQ and Games at Golf Club
Florida Vacation with pool fun for families
Enjoy meals in this dining area with a round table and four chairs, offering a view of the pool and lush surroundings.

Florida Vacation with pool fun for families

9.6 out of 10, Exceptional, (30)
"The place is perfectly located and clean. Loved it "
The price is CA $176
CA $481 total
includes taxes & fees
Sep 8 - Sep 9
Florida Vacation with pool fun for families
Tranquil 3-bedroom house in Sanford with AC, WiFi
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, coffee maker, and ample counter space.

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 $161
CA $329 total
includes taxes & fees
Aug 14 - Aug 15
Tranquil 3-bedroom house in Sanford with AC, WiFi
Sunny 5-bedroom Family Central Florida Getaway - AC, WiFi & Private Garden
Outdoor dining

Sunny 5-bedroom Family Central Florida Getaway - AC, WiFi & Private Garden

Sunny 5-bedroom Family Central Florida Getaway - AC, WiFi & Private Garden
House close to Downtown Orlando has Walking trail and next to Baldwin Park Lake
Enjoy cooking in this well-lit kitchen with a refrigerator, oven, and microwave, plus ample storage and a spacious island.

House close to Downtown Orlando has Walking trail and next to Baldwin Park Lake

9.8 out of 10, Exceptional, (16)
"Our VRBO was great and the area was great. Baldwin Park is a darling community with great walking paths and plenty of beautiful views. Close to everything! Such an enjoyable stay!"
House close to Downtown Orlando has Walking trail and next to Baldwin Park Lake
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Was great experience "
David 2-night trip
Posted 6 hours ago
Rosen Inn at Pointe Orlando