Windward Acres Vacation Rentals

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Vacation Rentals in Windward Acres

Villas By the Sea Resort & Conference Center
3.0 star property
8.4 out of 10, Very Good, (1078)
"This is our second visit to the Villas. It is a great location, clean and quiet!"
United States
Megan
Villas By the Sea Resort & Conference Center
Ocean Lodge Resort
4.0 star property
8.4 out of 10, Very Good, (331)
"3rd Timor staying there everything was great"
United States
James
Ocean Lodge Resort
905 Seaside ~ History, Luxury, Pet, Pool, King Bds
9.8 out of 10, Exceptional, (19)
"Absolutely perfect house on idyllic street! Plenty to do in area and amazing beach nearby, but the you will want to keep time free just to enjoy this beautiful house. "
United States
Erica O.
$514 nightly
The price is $514
Nov 4 - Nov 5
Total with taxes and fees
905 Seaside ~ History, Luxury, Pet, Pool, King Bds
Charming Getaway w/ a Kitchenette & Free WiFi - Walk to the Beach
9.2 out of 10, Wonderful, (104)
"Really cozy and great beach access."
United States
Renee O.
Charming Getaway w/ a Kitchenette & Free WiFi - Walk to the Beach
On The Beach With 2 Bikes And Pool
9.4 out of 10, Exceptional, (132)
"Totally enjoyed our week in this pet-friendly condo. Great location for many reasons….including being at the beach & proximity to multiple wonderful restaurants. Ben was very responsive & helpful before & during our stay."
United States
Gregory Y.
On The Beach With 2 Bikes And Pool
Stunning Rooftop Views. Prime Island Location
9.6 out of 10, Exceptional, (176)
"Great spot for family get together!!Cooked in most nights with large family but plenty of room for grands ranging from 25 to 3"
United States
Lynne S.
Stunning Rooftop Views. Prime Island Location
Great Location Unique Luxury Cottage- Sleeps 3 Spa Shower Close to Sea Island
10.0 out of 10, Exceptional, (282)
"Fantastic place!"
United States
Kirk J.
Great Location Unique Luxury Cottage- Sleeps 3 Spa Shower Close to Sea Island
Steps to East Beach & Pet Friendly w/ 2 King Beds
9.2 out of 10, Wonderful, (23)
"Quiet location 5 minutes from the beach!Our host was responsive to any questions or concerns. Restaurants a plenty nearby!"
United States
Laura O.
$297 nightly
The price is $339
Oct 29 - Oct 30
Total with taxes and fees
Steps to East Beach & Pet Friendly w/ 2 King Beds
Best Location NO STEPS All Ground Level Gated Condo Pool Just Remodeled Quiet
4.0 star property
9.8 out of 10, Exceptional, (156)
"The place was amazing and very easy to locate n very convenient to the grocery store and other shops."
United States
Jessica C.
Best Location NO STEPS All Ground Level Gated Condo Pool Just Remodeled Quiet
The Sea Gate
4.0 star property
9.6 out of 10, Exceptional, (592)
"All was great! "
United States
Wendy
$249 nightly
The price is $289
Oct 28 - Oct 29
Total with taxes and fees
The Sea Gate
Free Golf Cart! Heated Pool! 2 Kings, 1Queen, 2 Doubles- Walk to Beach & Village
9.8 out of 10, Exceptional, (58)
"The house was everything we needed and more! The location was fantastic and the golf cart was so convenient! We WILL stay here again! Thank you Darlene for sharing your lovely property!"
United States
Sarah R.
$731 nightly
The price is $827
Oct 28 - Oct 29
Total with taxes and fees
Free Golf Cart! Heated Pool! 2 Kings, 1Queen, 2 Doubles- Walk to Beach & Village
3 Bed 2 bath house sleeps 14, mins from beach and pier.
10.0 out of 10, Exceptional, (106)
"Very comfortable, clean, and great location. We had 4 adults and 3 children. Will definitely stay there again!"
United States
Stephanie H.
3 Bed 2 bath house sleeps 14, mins from beach and pier.
Coastaway for your getaway or longer stay on SSI!
10.0 out of 10, Exceptional, (43)
"Great hosts very clean great location"
United States
Machelle R.
Coastaway for your getaway or longer stay on SSI!
Driftwood Beach adjacent, off season rate, 20% off week, BEACH FRONT!
9.6 out of 10, Exceptional, (52)
"Host was helpful and informative regarding check - in and amenities. Condo was clean and well stocked with linens etc. Even had some pool toys. Our family really enjoyed the stay, especially the sea views in the mornings."
United States
Angel H.
Driftwood Beach adjacent, off season rate, 20% off week, BEACH FRONT!
Classic Marshfront Sea Island Cottage! Huge Game Room! Steps to The Beach! BIKES
10.0 out of 10, Exceptional, (108)
"Great cottage for a family trip!"
United States
christopher h.
Classic Marshfront Sea Island Cottage! Huge Game Room! Steps to The Beach! BIKES
Pet friendly, beautiful mid island cottage only 3 miles from the beach!
10.0 out of 10, Exceptional, (59)
"We loved our stay! Everything was super close and the house was very cozy."
United States
Karsen B.
Pet friendly, beautiful mid island cottage only 3 miles from the beach!
Oceanfront Condominium with pool, private boardwalk to beach with ramp.
9.8 out of 10, Exceptional, (33)
"Perfect accommodations for our family of 6! We loved the pool and being able to walk right down to the beach! Close to restaurants and shopping too!"
United States
Katie K.
Oceanfront Condominium with pool, private boardwalk to beach with ramp.
3BR/2BA, Sleeps 6 and Pet Friendly. Short walk to the Beach and Pier Village!
10.0 out of 10, Exceptional, (10)
"Just a short walk to everthing."
United States
Penny B.
3BR/2BA, Sleeps 6 and Pet Friendly. Short walk to the Beach and Pier Village!
Best Location 1 bed 1 bath gated condo. Available for RSM Classic tournament
10.0 out of 10, Exceptional, (249)
"Good place to stay if you just need to sleep"
United States
Jackie
Best Location 1 bed 1 bath gated condo. Available for RSM Classic tournament
Savannah Cottage SSI- Family-Run- Steps to Beach with Heated Pool & Golf Cart
10.0 out of 10, Exceptional, (15)
"The property was amazing, well stocked with everything we needed, clean, spacious. Host was amazing throughout! "
United States
morgan C.
$1,015 nightly
The price is $1,146
Nov 5 - Nov 6
Total with taxes and fees
Savannah Cottage SSI- Family-Run- Steps to Beach with Heated Pool & Golf Cart
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.