Windward Acres Vacation Rentals

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Vacation Rentals in Windward Acres

Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.
10.0 out of 10, Exceptional, (80)
"Very Clean, Host wanted to make sure everything was to our expectations and some. Great Stay!!"
United States
lance m.
$159 nightly
The price is $183
Oct 29 - Oct 30
Total with taxes and fees
Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.
The Sea Gate
4.0 star property
9.6 out of 10, Exceptional, (593)
"All was great! "
United States
Wendy
$249 nightly
The price is $289
Oct 29 - Oct 30
Total with taxes and fees
The Sea Gate
Beach Cottage -optional BIKES - Walk 2 Shops & Fun
9.8 out of 10, Exceptional, (116)
"We had a great stay!"
United States
Benjamin B.
$151 nightly
The price is $174
Nov 9 - Nov 10
Total with taxes and fees
Beach Cottage -optional BIKES - Walk 2 Shops & Fun
Beach House -optional BIKES - Walk 2 Shops & Fun
9.8 out of 10, Exceptional, (124)
"Nice place to stay in a good area. "
United States
Sheila
$184 nightly
The price is $212
Nov 20 - Nov 21
Total with taxes and fees
Beach House -optional BIKES - Walk 2 Shops & Fun
Great One Room with Full Bath Guest House!
10.0 out of 10, Exceptional, (28)
"Small but nice, clean place to stay!"
United States
gerald
$126 nightly
The price is $144
Oct 30 - Oct 31
Total with taxes and fees
Great One Room with Full Bath Guest House!
Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.
8.8 out of 10, Excellent, (3)
"Wonderful place to stay. Had everything we needed. Clean and fresh on arrival. "
United States
Lydia R.
$159 nightly
The price is $183
Oct 29 - Oct 30
Total with taxes and fees
Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.
Swim, bike, relax: South Side Condo near East Beach with 4 bikes included
10.0 out of 10, Exceptional, (29)
"Perfect for the best girls weekend! "
United States
Roy C.
$287 nightly
The price is $328
Oct 29 - Oct 30
Total with taxes and fees
Swim, bike, relax: South Side Condo near East Beach with 4 bikes included
Coastal Comfort
10.0 out of 10, Exceptional, (1)
"We had a great stay, only 7 minutes to the beach!"
United States
Stacy M.
$266 nightly
The price is $303
Oct 29 - Oct 30
Total with taxes and fees
Coastal Comfort
Beach Air -optional BIKES-Pool-Walk 2 Pier Village
10.0 out of 10, Exceptional, (135)
"Absolutely loved this stay!!!"
United States
Lura B.
$166 nightly
The price is $191
Nov 2 - Nov 3
Total with taxes and fees
Beach Air -optional BIKES-Pool-Walk 2 Pier Village
Private hot tub and seasonally heated pool.
9.2 out of 10, Wonderful, (75)
"Wonderful weekend stay with wife, Apartment was clean was close to everything. The neighborhood was quiet and relaxing. Pool was great and so was the spa, overall great stay "
United States
Felix M.
$168 nightly
The price is $194
Nov 2 - Nov 3
Total with taxes and fees
Private hot tub and seasonally heated pool.
La Vie Insulaire -optional BIKES–Walk 2 Redfern Village, shops, and restaurants!
9.8 out of 10, Exceptional, (12)
"Close to everything. Condo was perfect for our needs. "
United States
Alan
$216 nightly
The price is $248
Nov 17 - Nov 18
Total with taxes and fees
La Vie Insulaire -optional BIKES–Walk 2 Redfern Village, shops, and restaurants!
Apartment near downtown.
9.8 out of 10, Exceptional, (12)
"Nice place, nice hood, nice time."
United States
mark w.
$210 nightly
The price is $242
Nov 3 - Nov 4
Total with taxes and fees
Apartment near downtown.
Cowboy Studio, Pet Friendly, Walk to Village
9.8 out of 10, Exceptional, (75)
"Great little place with everything a couple could need and convenient walk to SSI Village!"
United States
Clark R.
$450 nightly
The price is $489
Oct 29 - Oct 30
Total with taxes and fees
Cowboy Studio, Pet Friendly, Walk to Village
Updated Condo, Steps to Tennis + Pickleball Courts, Beach and Village, w/ a Pool
10.0 out of 10, Exceptional, (22)
"The property was very nice and we enjoyed the easy walk into the village. Would definitely stay here again! "
United States
Michelle W.
$326 nightly
The price is $371
Oct 29 - Oct 30
Total with taxes and fees
Updated Condo, Steps to Tennis + Pickleball Courts, Beach and Village, w/ a Pool
Pool View - optional BIKES - Walk 2 Pier Village
9.8 out of 10, Exceptional, (87)
"We would stay here again. Nice view of pool. "
United States
David M.
$187 nightly
The price is $215
Nov 2 - Nov 3
Total with taxes and fees
Pool View - optional BIKES - Walk 2 Pier Village
Fall Special - steps to shops and pier/village!
9.2 out of 10, Wonderful, (24)
"Great location- Very Nice Condo"
United States
Tom D.
$308 nightly
The price is $346
Oct 29 - Oct 30
Total with taxes and fees
Fall Special - steps to shops and pier/village!
Cottage on East Beach, 14th St, Walk to Beach! Pet Friendly with Fenced Backyard & Screened Porch
9.0 out of 10, Wonderful, (6)
"Great place with everything you need."
United States
Scott C.
Cottage on East Beach, 14th St, Walk to Beach! Pet Friendly with Fenced Backyard & Screened Porch
Private Dock + Fire Pit: Riverfront Darien Cottage
3.0 star property
10.0 out of 10, Exceptional, (3)
"Cute and comfortable little house with amazing views of the river. Walkable to historic area and restaurants. Had an excellent stay, definitely recommend for relaxing get away!"
United States
Kelly
$330 nightly
The price is $374
Nov 6 - Nov 7
Total with taxes and fees
Private Dock + Fire Pit: Riverfront Darien Cottage
♥ of SSI Bungalow 2, Quick walk to beach and food ☼
9.8 out of 10, Exceptional, (6)
"Very nice! Thank you!"
United States
Sheila T.
$208 nightly
The price is $239
Oct 29 - Oct 30
Total with taxes and fees
♥ of SSI Bungalow 2, Quick walk to beach and food ☼
Beautiful South Island, Fully Remodeled, 3 Bedroom Escape with Sunroom
10.0 out of 10, Exceptional, (38)
"It was very nice and clean. Woukd definitely stay there again. "
United States
SUSAN T.
$352 nightly
The price is $401
Oct 29 - Oct 30
Total with taxes and fees
Beautiful South Island, Fully Remodeled, 3 Bedroom Escape with Sunroom
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 Windward Acres Hotel Reviews

Find out more about Windward Acres

Everything you need to know about Windward Acres vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Acres vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windward Acres vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windward Acres vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windward Acres. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windward Acres in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $289 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windward Acres rentals

At Expedia, we put the best Windward Acres vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windward Acres rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windward Acres vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windward Acres. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Windward Acres?

Yes, we offer vacation rentals close to top points of interest in Windward Acres, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Windward Acres has to offer?

3 Bed 2 bath house sleeps 14, mins from beach and pier.: This vacation home rental outside of Windward Acres is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Windward Acres?

Explore the area and family-friendly sights such as Summer Waves Water Park, or get out into nature at a spot like Mary Ross Waterfront Park. In the larger area, you’ll find Glynn Place Mall and Sea Palms Resort Golf Course.

What are vacation rentals like in Windward Acres?

Vacation rentals are private properties you can book for several days or longer in Windward Acres. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.