Winter Woods Holiday Rentals

Compare Villas, Resorts, & Rentals in Winter Woods, Port Orange, Florida, USA

New Coastal Cottage Near the Ocean
10.0 (1 Review)
4 Bedrooms 8 Guests
From CA $76 per night
|
10.0 (3 Reviews)
2 Bedrooms 4 Guests
8.8 (1003 Reviews)
1 Bedroom 2 Guests
From CA $321 per night
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9.6 (5 Reviews)
4 Bedrooms 9 Guests
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7.8 (1003 Reviews)
1 Bedroom 2 Guests
New Luxury Pool & Spa Home near the Beach
New
3 Bedrooms 8 Guests
From CA $136 per night
9.3 (4 Reviews)
2 Bedrooms 4 Guests
7.8 (598 Reviews)
1 Bedroom 2 Guests
From CA $241 per night
9.0 (7 Reviews)
1 Bedroom 2 Guests
From CA $188 per night
10.0 (27 Reviews)
1 Bedroom 2 Guests
|
9.0 (2 Reviews)
3 Bedrooms 6 Guests
From CA $243 per night
|
9.0 (1 Review)
3 Bedrooms 8 Guests
10.0 (5 Reviews)
1 Bedroom 2 Guests
|
8.5 (8 Reviews)
3 Bedrooms 6 Guests
|
8.0 (4 Reviews)
4 Bedrooms 8 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
|
7.5 (2 Reviews)
3 Bedrooms 8 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
From CA $276 per night
|
7.5 (2 Reviews)
2 Bedrooms 6 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
From CA $473 per night
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7.3 (3 Reviews)
4 Bedrooms 8 Guests
7.0 (1 Review)
3 Bedrooms 8 Guests
From CA $285 per night
4.0 (1 Review)
1 Bedroom 6 Guests
From CA $920 per night
|
New
1 Bedroom 10 Guests
From CA $338 per night
|
New
3 Bedrooms 5 Guests
From CA $304 per night
|
New
2 Bedrooms 4 Guests
From CA $325 per night
9.6 (4 Reviews)
2 Bedrooms 4 Guests
9.0 (15 Reviews)
2 Bedrooms 6 Guests
From CA $365 per night
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2.0 (1 Review)
1 Bedroom 2 Guests
10.0 (3 Reviews)
3 Bedrooms 8 Guests
|
New
3 Bedrooms 8 Guests
10.0 (3 Reviews)
3 Bedrooms 8 Guests
New
1 Bedroom 6 Guests
10.0 (2 Reviews)
4 Bedrooms 7 Guests
New
3 Bedrooms 10 Guests
10.0 (1 Review)
3 Bedrooms 8 Guests
|
8.5 (327 Reviews)
80 Bedrooms 39 Guests
From CA $261 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
|
7.7 (710 Reviews)
71 Bedrooms 25 Guests
7.4 (149 Reviews)
122 Bedrooms 18 Guests
|
9.7 (3 Reviews)
3 Bedrooms 6 Guests
9.8 (36 Reviews)
3 Bedrooms 6 Guests
From CA $131 per night
9.4 (5 Reviews)
1 Bedroom 4 Guests

About Casai's Private Villas and Holiday Rentals in Winter Woods

Discover more than 249 vacation rentals available in Winter Woods. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter Woods.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Woods, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter Woods. On average, places to stay near Winter Woods offer 879.67 ft², with nightly prices averaging CA $394.

With Casai, finding and comparing holiday rentals in Winter Woods is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Winter Woods?

What are the top holiday rentals in Winter Woods?

How many Casai.ca holiday rentals are available in Winter Woods?

As of 2025, Casai boasts over 249 properties listed in the Winter Woods area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Woods.

Nearby Neighborhood (3)

Neighborhood Property Count
Kingswood Vacation Rentals in Daytona Beach, Florida 225
Willow Run Vacation Rentals in Daytona Beach, Florida 184
Town Park Vacation Rentals in Daytona Beach, Florida 133