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Holiday Homes in Winter Springs

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in Winter Springs

Our top choices for Winter Springs holiday homes

Vista Cay Resort by Casiola Vacation Homes
3 outdoor pools, a heated pool, pool umbrellas, pool loungers

Vista Cay Resort by Casiola Vacation Homes

3.5 star property
8.8 out of 10, Excellent, (182)
"Excellent "
The price is NZ$675
includes taxes & fees
23 Aug - 24 Aug
Vista Cay Resort by Casiola Vacation Homes
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.

8.2 out of 10, Very good, (10)
"GREAT STAY"
The price is NZ$639
includes taxes & fees
4 Sept - 5 Sept
Blocks a way to Universal Studios. Full Single Family with pool, and amenities.
Quiet Oasis in Lovely Neighborhood
Pool

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (147)
"Hosts were wondeful. Nice quiet neighborhood. Our favorite part was definitely the pool. "
The price is NZ$326
includes taxes & fees
26 Aug - 27 Aug
Quiet Oasis in Lovely Neighborhood
Mid-century Modern Villa w/ Pool Near Universal
Smart TV, video games, printers

Mid-century Modern Villa w/ Pool Near Universal

10.0 out of 10, Exceptional, (7)
"Thank you nice place"
Mid-century Modern Villa w/ Pool Near Universal
Luxury Family Retreat • Sleeps 8 • Near Disney World
Private kitchen

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 NZ$324
includes taxes & fees
25 Aug - 26 Aug
Luxury Family Retreat • Sleeps 8 • Near Disney World
Near Universal, Disney & OCC Vista Cay town home
Outdoor pool, a heated pool

Near Universal, Disney & OCC Vista Cay town home

10.0 out of 10, Exceptional, (37)
"Nice place to stay. Other family members were in the community "
Near Universal, Disney & OCC Vista Cay town home
Luxury home
Fridge, microwave, oven, stovetop

Luxury home

9.6 out of 10, Exceptional, (5)
"Roomy, clean, excellent location."
Luxury home
Tiny tropical Orlando Univesal-Disney
Property grounds

Tiny tropical Orlando Univesal-Disney

6.4 out of 10, (13)
"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
Lake Front Suite -Close to all Attractions
Outdoor dining

Lake Front Suite -Close to all Attractions

9.4 out of 10, Exceptional, (80)
"The property was amazing. Would definitely stay there again !"
Lake Front Suite -Close to all Attractions
The Spellbinding | Exciting NEW home w/in-home entertainment near top shopping
Pool

The Spellbinding | Exciting NEW home w/in-home entertainment near top shopping

2.5 star property
10.0 out of 10, Exceptional, (7)
"Perfect spot for our family! Beds were super comfy and pool was the perfect way to end our days after the parks. We will definitely be back. "
The Spellbinding | Exciting NEW home w/in-home entertainment near top shopping
Eastpark. Pet friendly! Lake Nona
Interior

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 NZ$526
includes taxes & fees
22 Sept - 23 Sept
Eastpark. Pet friendly! Lake Nona
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, (32)
"Property was clean and tidy, listed just as described. Communications with owner were easy and informative. Will definitely stay again "
Spacious Poolside Home --- 5 min from manatee swimming hole
The Epic Toronto Vista Cay Orlando
Exterior

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
Interior

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
The Villa Orlando@College Park. Sleeps16.
Fridge, microwave, oven, stovetop

The Villa Orlando@College Park. Sleeps16.

10.0 out of 10, Exceptional, (12)
"Great location, just as advertised "
The price is NZ$761
includes taxes & fees
25 Aug - 26 Aug
The Villa Orlando@College Park. Sleeps16.
ORLANDO BUDGET FRIENDLY HOUSE/ PRIVATE POOL/SLEEPS 12/ CLOSE TO EVERYTHING
Property grounds

ORLANDO BUDGET FRIENDLY HOUSE/ PRIVATE POOL/SLEEPS 12/ CLOSE TO EVERYTHING

9.8 out of 10, Exceptional, (30)
"This is our second time booking and our stay was just as great as the first time. Great Location and a Great Host. I look forward to booking again soon"
ORLANDO BUDGET FRIENDLY HOUSE/ PRIVATE POOL/SLEEPS 12/ CLOSE TO EVERYTHING
Upstay - Home w Garden, BBQ and Games at Golf Club
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very good, (6)
"it was nice, if we want go to swimming its just in the aria."
Upstay - Home w Garden, BBQ and Games at Golf Club
Pool, Jacuzzi, Cabana Oh My!! Welcome to Paradise
Terrace/patio

Pool, Jacuzzi, Cabana Oh My!! Welcome to Paradise

9.4 out of 10, Exceptional, (35)
"We were so grateful for the private outdoor space. When we were at the property, we spent our time in the pool and outdoor cabana.Host was very responsive to communication."
Pool, Jacuzzi, Cabana Oh My!! Welcome to Paradise
Charming 4-bedroom house with pool table in BEAUTIFUL Orlando
Living area

Charming 4-bedroom house with pool table in BEAUTIFUL Orlando

7.4 out of 10, Good, (6)
The price is NZ$659
includes taxes & fees
13 Sept - 14 Sept
Charming 4-bedroom house with pool table in BEAUTIFUL Orlando
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Smart TV

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

9.2 out of 10, Wonderful, (92)
"Good location close to fullsail university "
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
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

CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

10/10 Excellent
"Great "
Susan 5-night trip
Posted 7 hours ago
CoCo Key Hotel and Water Resort