Estia Villas - Vacation Rentals in Winter Park
New
Villa
1 Bedroom
4 Bathrooms
7 Guests
-
Balcony/Terrace -
Kitchen -
Internet -
Child Friendly
US $179
/Night
7 Nights - $1,253
House
10.0
(
2 Reviews
)
3 Bedrooms
4 Bathrooms
19 Guests
2195.84 ft²
-
Hot Tub -
Breakfast -
Parking -
Spa
US $549
/Night
7 Nights - $3,843
Villa
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $269
/Night
7 Nights - $1,881
House
10.0
(
2 Reviews
)
3 Bedrooms
3 Bathrooms
12 Guests
1797.57 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Spa
US $517
/Night
7 Nights - $3,619
Villa
4.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Kitchen
-
Internet
-
Child Friendly
-
Laundry
US $250
/Night
7 Nights - $1,750
House
10.0
(
2 Reviews
)
3 Bedrooms
4 Bathrooms
10 Guests
2497.23 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Spa
US $428
/Night
7 Nights - $2,998
House
10.0
(
1 Review
)
4 Bedrooms
5 Bathrooms
23 Guests
3003.13 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Spa
US $703
/Night
7 Nights - $4,921
Villa
10.0
(
1 Review
)
5 Bedrooms
3 Bathrooms
10 Guests
3498.27 ft²
-
Parking
-
Spa
-
Skiing -
Internet
US $435
/Night
7 Nights - $3,045
See More Winter Park Vacation Rentals
Luxury Places to Stay in Winter Park
Over 2770+
Luxury Places to Stay in or Near Winter Park
New
House
4 Bedrooms
3 Bathrooms
9 Guests
258.33 ft²
-
Hot Tub
-
Internet
-
Child Friendly
-
Wellness Facilities
US $9,132
/Night
7 Nights - $63,922
New
House
3 Bedrooms
3 Bathrooms
7 Guests
150.69 ft²
-
Internet
-
Child Friendly
-
Sports/Activities -
Security/Safety
US $9,099
/Night
7 Nights - $63,690
New
Apartment
3 Bedrooms
3 Bathrooms
8 Guests
204.51 ft²
-
Hot Tub
-
Internet
-
Child Friendly
-
Wellness Facilities
US $9,099
/Night
7 Nights - $63,690
New
House
2 Bedrooms
2 Bathrooms
8 Guests
139.93 ft²
-
Hot Tub
-
Pool -
Internet
-
Child Friendly
US $9,090
/Night
7 Nights - $63,628
House
4 Bedrooms
4 Bathrooms
12 Guests
3745.84 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Internet
US $5,560
/Night
7 Nights - $38,920
House
10.0
(
2 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
3600 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $3,251
/Night
7 Nights - $22,755
House
11 Bedrooms
8 Bathrooms
19 Guests
6727.44 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Internet
US $3,230
/Night
7 Nights - $22,610
House
5 Bedrooms
6 Bathrooms
18 Guests
5005.22 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Spa
US $3,166
/Night
7 Nights - $22,161
See More Winter Park Luxury Vacation Rentals
Find More Winter Park Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Winter Park
Over 835+
Top-Rated Vacation Rentals with a Pool in or Near Winter Park
Apartment
10.0
(
233 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1184 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $378
/Night
7 Nights - $2,644
New
Condo
10.0
(
200 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $319
/Night
7 Nights - $2,232
Condo
10.0
(
177 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $275
/Night
7 Nights - $1,926
Condo
10.0
(
165 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
950 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $240
/Night
7 Nights - $1,679
Condo
10.0
(
122 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1081 ft²
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Kitchen
US $365
/Night
7 Nights - $2,553
Condo
10.0
(
120 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
450 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $232
/Night
7 Nights - $1,624
Condo
10.0
(
115 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1507 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $476
/Night
7 Nights - $3,333
New
House
10.0
(
97 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1500 ft²
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $371
/Night
7 Nights - $2,597
Pet-Friendly Vacation Rentals in Winter Park
Over 331+
Pet-Friendly Vacation Rentals in or Near Winter Park
Apartment
8.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
5 Guests
850.35 ft²
-
Private Pool
-
Hot Tub
-
Breakfast
-
Parking
US $227
/Night
7 Nights - $1,589
US $342
/Night
7 Nights - $2,391
House
10.0
(
103 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $459
/Night
7 Nights - $3,211
Condo
9.6
(
138 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1600 ft²
-
Hot Tub
-
Parking
-
Spa
-
Balcony/Terrace
US $378
/Night
7 Nights - $2,648
Condo
9.4
(
118 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
750 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $229
/Night
7 Nights - $1,604
Cabin
9.0
(
22 Reviews
)
5 Bedrooms
3 Bathrooms
14 Guests
4500 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,206
/Night
7 Nights - $8,439
House
9.6
(
48 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1250 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $349
/Night
7 Nights - $2,442
House
9.2
(
21 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2790 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $571
/Night
7 Nights - $4,000
See More Pet-Friendly Vacation Rentals in Winter Park on PetFriendly.io
Large Vacation Homes & Villas in Winter Park
Over 571+
Large Vacation Homes & Villas in or Near Winter Park
House
9.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
10 Guests
1646.88 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Kitchen
US $342
/Night
7 Nights - $2,394
US $1,350
/Night
7 Nights - $9,451
House
9.8
(
148 Reviews
)
9 Bedrooms
8 Bathrooms
22 Guests
-
Hot Tub
-
Parking
-
Ocean View -
Balcony/Terrace
US $2,368
/Night
7 Nights - $16,578
Condo
9.6
(
57 Reviews
)
3 Bedrooms
3 Bathrooms
11 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $338
/Night
7 Nights - $2,363
House
9.6
(
54 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
2150 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $565
/Night
7 Nights - $3,955
Condo
10.0
(
89 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
1507 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $341
/Night
7 Nights - $2,386
House
10.0
(
76 Reviews
)
5 Bedrooms
4 Bathrooms
16 Guests
5460 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $708
/Night
7 Nights - $4,956
House
9.6
(
37 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1744 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $296
/Night
7 Nights - $2,075
See More Family Vacation Rentals in Winter Park on FVR
Wheelchair Accessible Vacation Homes in Winter Park
Over 581+
Wheelchair Accessible Vacation Homes in or Near Winter Park
Apartment
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
570.49 ft²
-
Hot Tub
-
Parking
-
Internet
-
Child Friendly
US $243
/Night
7 Nights - $1,701
Condo
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Hot Tub
-
Skiing
-
Kitchen
-
Internet
US $835
/Night
7 Nights - $5,847
Condo
10.0
(
151 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
635 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $204
/Night
7 Nights - $1,426
House
9.8
(
107 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $357
/Night
7 Nights - $2,497
House
9.2
(
55 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $346
/Night
7 Nights - $2,424
House
9.6
(
67 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $379
/Night
7 Nights - $2,652
House
9.4
(
81 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $389
/Night
7 Nights - $2,721
New
Condo
9.8
(
80 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
814 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $206
/Night
7 Nights - $1,439
Winter Park Vacation Rentals and Airbnb Places to Stay Under $200
Over 355+
Winter Park Vacation Rentals and Airbnb Places to Stay Under $200
House
1 Bedroom
2 Bathrooms
4 Guests
527.43 ft²
-
Parking
-
Internet
-
Child Friendly
-
Wheelchair Accessible
US $146
/Night
7 Nights - $1,022
House
9.8
(
152 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Skiing
-
Balcony/Terrace
-
Kitchen
US $136
/Night
7 Nights - $954
New
Condo
9.8
(
168 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $184
/Night
7 Nights - $1,285
Condo
9.8
(
118 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
450 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $117
/Night
7 Nights - $819
Condo
10.0
(
97 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
630 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $195
/Night
7 Nights - $1,368
Apartment
10.0
(
91 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
443 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $160
/Night
7 Nights - $1,121
Apartment
10.0
(
88 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
443 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $172
/Night
7 Nights - $1,201
Condo
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $182
/Night
7 Nights - $1,274
See More Winter Park Vacation Rental Deals
Instantly Bookable Vacation Homes in Winter Park
Over 1694+
Instantly Bookable Vacation Homes in or Near Winter Park
Apartment
10.0
(
27 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
801 ft²
-
Hot Tub
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $302
/Night
7 Nights - $2,114
House
9.6
(
100 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1432 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $407
/Night
7 Nights - $2,852
House
9.8
(
72 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $218
/Night
7 Nights - $1,524
New
House
9.8
(
46 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
1656 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $335
/Night
7 Nights - $2,344
House
9.8
(
41 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
1629 ft²
-
Hot Tub
-
Balcony/Terrace
-
Kitchen
-
Internet
US $309
/Night
7 Nights - $2,162
Condo
9.4
(
140 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
569 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $221
/Night
7 Nights - $1,547
Condo
9.4
(
38 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
569 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $206
/Night
7 Nights - $1,439
Condo
10.0
(
144 Reviews
)
2 Bedrooms
2 Bathrooms
10 Guests
1050 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $316
/Night
7 Nights - $2,213
About Winter Park Vacation Rentals
With more than 83 Winter Park vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winter Park.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Winter Park, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winter Park. Places to stay near Winter Park are 2251.6 ft² on average, with prices averaging US $600 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Winter Park with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Winter Park
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winter Park.
Weather in Winter Park
View the weather forecast for Winter Park before booking your Winter Park Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Winter Park, CO
Estiavillas offers a large selection of top attractions around Winter Park. Research things to do on your vacation before you visit Winter Park.
Winter Park Ski Resort
Village Cabriolet Ski Lift
Zephyr Express Ski Lift
Amaze'n Maze Winter Park
Winter Park Visitor Center
Trestle Bike Park
Olympia Express Ski Lift
Arrow Ski Lift
Blue Sky Massage
Discovery Ski LIft
Challenger Ski Lift
Iron Horse Ski Lift
Moffat Tunnel West Portal
Bella Vita
Pioneer Express Ski Lift
Eskimo Express Ski Lift
Super Gauge Express Ski Lift
Black Tie Ski Rentals of Winter Park
Body Kneads Massage and Pilates
Looking Glass Ski Lift
Other Places to Stay Near Winter Park, CO
Hideaway Village South
3,870 Properties
Elk Court Cabins
3,799 Properties
Bella Vita
3,526 Properties
Blue Sky Massage
3,525 Properties
Winter Park Visitor Center
3,517 Properties
Body Kneads Massage and Pilates
3,353 Properties
Grand Park Community Recreation Center
2,760 Properties
Pioneer Express Ski Lift
2,571 Properties
Black Tie Ski Rentals of Winter Park
2,550 Properties
Eskimo Express Ski Lift
2,548 Properties
Old Town
77 Properties
Bear Crossing
27 Properties
Complexes around Winter Park, CO
Zephyr Mountain Lodge Park
256 Properties
Slopeside
25 Properties
Crossing Founders Pointe
19 Properties
Trailhead Lodge
19 Properties
Villa Resort Activities Equipment Rentals
12 Properties
Iron Horse Resort
10 Properties
Zephyr Mountain Lodge Continental Divide
10 Properties
Zephyr Mountain Lodge Ski Slope
8 Properties
Spectacular Zephyr Mountain Lodge Village
6 Properties
Zephyr Mountain Lodge Furnishings
5 Properties
Country Haus Getaway
4 Properties
Crestview
4 Properties
Red Quill Village
4 Properties
Cozy Zephyr Mountain Lodge Of Arapahoe National Forest
3 Properties
Leland Creek
3 Properties
Winter Park Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Winter Park?
There are a lot of options in Winter Park. If you plan on staying in the Winter Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winter Park:
- Downtown WP Villa 865 I Private Hot Tub I Great Views I Activity Program
- Mountain Villa 301 Next To Resort I Private Hot Tub I Great Views I Activity Program
- Downtown WP Villa 305 I Private Hot Tub I Views I Activity Program
- Downtown WP Villa 307 I Private Hot Tub I Views I Activity Program
- Arrow at Winter Park Unit 284
- Mountain Villa 502 Next To WP Resort I Private Hot Tub I Great Views I Activity Program
- Downtown WP Villa 268 I Rooftop Hot Tub I Great Views I Activity Program
- Slopeside Villa 90 I Hot Tub I Great Views I Activity Program
- Slopeside Villa 136 I Fantastic Ski Views I Steamroom I Activity Program
- Downtown WP Pond Villa 558 I Private Hot Tub I Great Views I Activity Program
How many vacation rentals have private pools in Winter Park?
There are 96 vacation rentals with private pools near Winter Park. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Winter Park are best for families?
If you are looking for a family-friendly vacation home in Winter Park, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winter Park:
How many vacation rentals are available in Winter Park?
Currently, the total number of properties listed in 2026 is over 83 in the Winter Park area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winter Park.
