Estia Villas - Vacation Rentals in Winter Park
Villa
9.4
(
19 Reviews
)
4 Bedrooms
2 Bathrooms
6 Guests
11625 ft²
-
Hot Tub -
Parking -
Pool -
Balcony/Terrace
US $276
/Night
7 Nights - $1,930
Villa
1 Bedroom
1 Bathroom
-
Parking
-
Child Friendly -
Laundry -
Wellness Facilities
US $134
/Night
7 Nights - $941
Villa
7.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $100
/Night
7 Nights - $699
Villa
4.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Air Conditioner
-
Child Friendly
-
Laundry
-
Bedding/Linens
US $140
/Night
7 Nights - $980
Villa
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool -
Pool
-
Kitchen
-
Air Conditioner
US $128
/Night
7 Nights - $896
See More Winter Park Vacation Rentals
Luxury Places to Stay in Winter Park
Over 182+
Luxury Places to Stay in or Near Winter Park
New
House
5 Bedrooms
4 Bathrooms
10 Guests
-
Air Conditioner
-
Internet -
Child Friendly
-
Laundry
US $607
/Night
7 Nights - $4,248
New
Hotel
435 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $503
/Night
7 Nights - $3,518
New
House
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $479
/Night
7 Nights - $3,355
New
Condo
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Ocean View -
Balcony/Terrace
-
View
US $456
/Night
7 Nights - $3,192
New
Hotel
350 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $453
/Night
7 Nights - $3,172
New
Hotel
323 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $451
/Night
7 Nights - $3,158
New
Hotel
448 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $446
/Night
7 Nights - $3,121
New
Hotel
400 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $443
/Night
7 Nights - $3,100
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 59+
Top-Rated Vacation Rentals with a Pool in or Near Winter Park
Apartment
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1950 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $281
/Night
7 Nights - $1,967
House
10.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2507 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $409
/Night
7 Nights - $2,863
Apartment
10.0
(
4 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1252 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $146
/Night
7 Nights - $1,020
House
10.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
850 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $144
/Night
7 Nights - $1,011
House
10.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
850 ft²
-
Pool
-
Internet
-
Pet Friendly -
Child Friendly
US $128
/Night
7 Nights - $899
Apartment
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1950 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $281
/Night
7 Nights - $1,964
House
10.0
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
5 Guests
1377.78 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Air Conditioner
US $242
/Night
7 Nights - $1,694
Apartment
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
952 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $135
/Night
7 Nights - $942
Pet-Friendly Vacation Rentals in Winter Park
Over 81+
Pet-Friendly Vacation Rentals in or Near Winter Park
Apartment
2 Bedrooms
1 Bathroom
4 Guests
1184 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $142
/Night
7 Nights - $993
House
9.0
(
1 Review
)
1 Bedroom
3 Bathrooms
12 Guests
2002.09 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
US $349
/Night
7 Nights - $2,444
House
9.8
(
12 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $197
/Night
7 Nights - $1,376
Cottage
10.0
(
37 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $146
/Night
7 Nights - $1,024
House
10.0
(
8 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2000 ft²
-
Oceanfront -
Hot Tub
-
Parking
-
Ocean View
US $360
/Night
7 Nights - $2,518
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1266 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $176
/Night
7 Nights - $1,235
House
10.0
(
4 Reviews
)
4 Bedrooms
2 Bathrooms
18 Guests
1240 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $393
/Night
7 Nights - $2,749
House
10.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
890 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $117
/Night
7 Nights - $820
See More Pet-Friendly Vacation Rentals in Winter Park on PetFriendly.io
Large Vacation Homes & Villas in Winter Park
Over 12+
Large Vacation Homes & Villas in or Near Winter Park
House
10.0
(
1 Review
)
5 Bedrooms
2 Bathrooms
11 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $312
/Night
7 Nights - $2,184
House
1.0
(
1 Review
)
5 Bedrooms
2 Bathrooms
11 Guests
96.88 ft²
-
Parking
-
Air Conditioner
-
Pet Friendly
-
Child Friendly
US $71
/Night
7 Nights - $498
House
4.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
11 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $375
/Night
7 Nights - $2,625
New
House
5 Bedrooms
2 Bathrooms
15 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $347
/Night
7 Nights - $2,432
House
10.0
(
20 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $345
/Night
7 Nights - $2,415
House
4.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Private Pool
-
Pool
-
Kitchen
-
Air Conditioner
US $175
/Night
7 Nights - $1,225
House
3 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $492
/Night
7 Nights - $3,446
House
4 Bedrooms
4 Bathrooms
10 Guests
3000 ft²
-
Parking
-
Lake View -
Balcony/Terrace
-
View
US $351
/Night
7 Nights - $2,458
See More Family Vacation Rentals in Winter Park on FVR
Wheelchair Accessible Vacation Homes in Winter Park
Over 9+
Wheelchair Accessible Vacation Homes in or Near Winter Park
Apartment
3 Bedrooms
1 Bathroom
7 Guests
900 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $132
/Night
7 Nights - $924
Apartment
3 Bedrooms
2 Bathrooms
6 Guests
150.69 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $192
/Night
7 Nights - $1,346
US $366
/Night
7 Nights - $2,565
Apartment
1 Bedroom
1 Bathroom
2 Guests
301 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $392
/Night
7 Nights - $2,744
US $327
/Night
7 Nights - $2,290
US $208
/Night
7 Nights - $1,456
Hotel
8.5
(
106 Reviews
)
-
Breakfast -
EV Charge Station -
Parking
-
Balcony/Terrace
US $249
/Night
7 Nights - $1,743
Hotel
9.2
(
393 Reviews
)
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $181
/Night
7 Nights - $1,268
Winter Park Vacation Rentals and Airbnb Places to Stay Under $200
Over 80+
Winter Park Vacation Rentals and Airbnb Places to Stay Under $200
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $189
/Night
7 Nights - $1,325
Apartment
9.5
(
8 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
839.58 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
View
US $137
/Night
7 Nights - $957
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
952 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $155
/Night
7 Nights - $1,083
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
894 ft²
-
Pool
-
Ocean View
-
Balcony/Terrace
-
View
US $132
/Night
7 Nights - $923
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
952 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $131
/Night
7 Nights - $918
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $108
/Night
7 Nights - $753
House
9.6
(
27 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $190
/Night
7 Nights - $1,329
Apartment
9.6
(
4 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $171
/Night
7 Nights - $1,198
See More Winter Park Vacation Rental Deals
Instantly Bookable Vacation Homes in Winter Park
Over 79+
Instantly Bookable Vacation Homes in or Near Winter Park
House
10.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1195 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $265
/Night
7 Nights - $1,852
House
10.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1195 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $221
/Night
7 Nights - $1,545
New
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1116 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $267
/Night
7 Nights - $1,869
House
9.8
(
125 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
3000 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $415
/Night
7 Nights - $2,903
Condo
9.8
(
22 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
650 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $200
/Night
7 Nights - $1,403
House
9.8
(
17 Reviews
)
3 Bedrooms
1 Bathroom
5 Guests
11291 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $299
/Night
7 Nights - $2,090
Apartment
9.6
(
4 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
850 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $295
/Night
7 Nights - $2,067
Apartment
9.4
(
3 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $74
/Night
7 Nights - $519
About Winter Park Vacation Rentals
With more than 5 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 2325 ft² on average, with prices averaging US $156 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.
Top Rental Accommodation Types in Winter Park
| Type | Count |
|---|---|
| Villas | 5 |
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 38°F Low 2°F
March - May
High 55°F Low 18°F
June - August
High 75°F Low 34°F
September - November
High 67°F Low 19°F
Top Attractions Around Winter Park, FL
Estiavillas offers a large selection of top attractions around Winter Park. Research things to do on your vacation before you visit Winter Park.
Full Sail University
Rollins College
Winter Park Village
Kraft Azalea Gardens
Casa Feliz Historic Home Museum
Mead Garden
Lee Road Shopping Center
Morse Museum of American Art
Lake Virginia
Albin Polasek Museum and Sculpture Gardens
Crealde School of Art
All Fired Up
Winter Park Playhouse
Alfond Swimming Pool
Winter Park Country Club
Winter Park Corner Shopping Center
The Center of Winter Park Shopping Center
Virginia S. Nelson Rose Garden
Winter Pines Golf Club
Winter Park History Museum
Other Places to Stay Near Winter Park, FL
Mead Garden
728 Properties
Hollie Anna Shopping Center
573 Properties
Lake Rose
514 Properties
Winter Park Playhouse
512 Properties
Lake Virginia
510 Properties
Alfond Swimming Pool
507 Properties
Lee Road Shopping Center
489 Properties
All Fired Up
469 Properties
Cahall Sandspur Field
460 Properties
Hannibal Square Heritage Center
458 Properties
Cornell Fine Arts Museum
456 Properties
Goldenrod
178 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:
How many vacation rentals have private pools in Winter Park?
There are 13 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 5 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.
