Windward Acres Vacation Rentals

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Our top choices for Windward Acres vacation rentals

Coastal Home Near FLETC, St Simon's & Jekyll Island

Coastal Home Near FLETC, St Simon's & Jekyll Island
Glynco
9.0 out of 10, Wonderful, (4 reviews)
"Good location "
United States
James F.
The price is CA $137
CA $419 total
includes taxes & fees
May 3 - May 4
Coastal Home Near FLETC, St Simon's & Jekyll Island

Beach Cottage -optional BIKES - Walk 2 Shops & Fun

Beach Cottage -optional BIKES - Walk 2 Shops & Fun
Saint Simons Island
9.8 out of 10, Exceptional, (130 reviews)
"The location was close to the Saint Simons Village and it was an easy drive on and off the Island. "
United States
Zane S.
The price is CA $51
CA $235 total
includes taxes & fees
May 20 - May 21
Beach Cottage -optional BIKES - Walk 2 Shops & Fun

Great One Room with Full Bath Guest House!

Great One Room with Full Bath Guest House!
Darien
10.0 out of 10, Exceptional, (34 reviews)
"Exactly as described. Cute area of Darien, very historic. Walking distance to restaurants."
United States
Judith
The price is CA $94
CA $198 total
includes taxes & fees
May 4 - May 5
Great One Room with Full Bath Guest House!

Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.

Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.
Saint Simons Heights
8.8 out of 10, Excellent, (5 reviews)
"Wonderful place to stay. Had everything we needed. Clean and fresh on arrival. "
United States
Lydia R.
The price is CA $67
CA $287 total
includes taxes & fees
May 4 - May 5
Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.

Beach Air -optional BIKES-Pool-Walk 2 Pier Village

Beach Air -optional BIKES-Pool-Walk 2 Pier Village
St Simons
10.0 out of 10, Exceptional, (140 reviews)
"It was a awesome place to stay "
United States
Dilara L.
The price is CA $53
CA $260 total
includes taxes & fees
May 5 - May 6
Beach Air -optional BIKES-Pool-Walk 2 Pier Village

La Vie Insulaire -optional BIKES–Walk 2 Redfern Village, shops, and restaurants!

La Vie Insulaire -optional BIKES–Walk 2 Redfern Village, shops, and restaurants!
Saint Simons Heights
9.8 out of 10, Exceptional, (19 reviews)
"Nice place to stay close to all"
United States
Clay W.
The price is CA $80
CA $301 total
includes taxes & fees
May 6 - May 7
La Vie Insulaire -optional BIKES–Walk 2 Redfern Village, shops, and restaurants!

Beach House -optional BIKES - Walk 2 Shops & Fun

Beach House -optional BIKES - Walk 2 Shops & Fun
Saint Simons Island
9.8 out of 10, Exceptional, (137 reviews)
"The host was most welcoming and communicated with us well. The house was cleaned and well arranged. We had all we need to make our stay pleasant"
United States
Judeen R.
The price is CA $64
CA $275 total
includes taxes & fees
May 3 - May 4
Beach House -optional BIKES - Walk 2 Shops & Fun

Beach Walk -optional BIKES-Pool-Walk 2 PierVillage

Beach Walk -optional BIKES-Pool-Walk 2 PierVillage
Saint Simons Island
9.8 out of 10, Exceptional, (151 reviews)
"Such a nice quiet nice neighborhood. Excellent stay for the price."
United States
Heather
The price is CA $64
CA $276 total
includes taxes & fees
May 6 - May 7
Beach Walk -optional BIKES-Pool-Walk 2 PierVillage

Apartment near downtown.

Apartment near downtown.
St. Simons Island
9.4 out of 10, Exceptional, (13 reviews)
"Nice place, nice hood, nice time."
United States
mark w.
The price is CA $138
CA $393 total
includes taxes & fees
May 4 - May 5
Apartment near downtown.

Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.

Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.
Saint Simons Heights
10.0 out of 10, Exceptional, (85 reviews)
"Clean rooms/ great host/ shops nearby"
United States
Blair P.
The price is CA $67
CA $287 total
includes taxes & fees
May 4 - May 5
Beach Square – optional BIKES – Walk 2 Redfern Village, shops, and restaurants!.

Swim, bike, relax: South Side Condo near East Beach with 4 bikes included

Swim, bike, relax: South Side Condo near East Beach with 4 bikes included
St. Simons Island
9.8 out of 10, Exceptional, (34 reviews)
"Excellent communication with host regarding check-in. Incredibly comfortable beds. Great stay!"
United States
Melissa
The price is CA $159
CA $472 total
includes taxes & fees
May 4 - May 5
Swim, bike, relax: South Side Condo near East Beach with 4 bikes included

Beach Square 2 –optional BIKES – Walk 2 Redfern Village, shops, and restaurants!

Beach Square 2 –optional BIKES – Walk 2 Redfern Village, shops, and restaurants!
Saint Simons Heights
10.0 out of 10, Exceptional, (2 reviews)
"Nice place very pretty convenient location "
United States
Walter P.
The price is CA $80
CA $301 total
includes taxes & fees
May 6 - May 7
Beach Square 2 –optional BIKES – Walk 2 Redfern Village, shops, and restaurants!

Close Beach Access, Walk to Lighthouse & Village!

Close Beach Access, Walk to Lighthouse & Village!
St. Simons
9.6 out of 10, Exceptional, (18 reviews)
"Excellent location and the management company was very responsive and informative. "
United States
Olivia Y.
Close Beach Access, Walk to Lighthouse & Village!

♥ of SSI Bungalow, Quick walk to beach and food ☼

♥ of SSI Bungalow, Quick walk to beach and food ☼
St. Simons Island
10.0 out of 10, Exceptional, (12 reviews)
"Great place for a great weekend! Super clean and close to some great restaurants. "
United States
JT M.
The price is CA $144
CA $295 total
includes taxes & fees
May 4 - May 5
♥ of SSI Bungalow, Quick walk to beach and food ☼

Tiny House 20 Mins from Beach

Tiny House 20 Mins from Beach
Brunswick
10.0 out of 10, Exceptional, (1 review)
"Perfect little place to stay. Seemed a little sketchy at first. But after the first night that feeling went away. It was simplistic and had everything you needed for the little time you will actually spend there. "
United States
james s.
The price is CA $97
CA $242 total
includes taxes & fees
May 3 - May 4
Tiny House 20 Mins from Beach

Water View - optional BIKES - Walk 2 Pier Village

Water View - optional BIKES - Walk 2 Pier Village
St. Simons Island
10.0 out of 10, Exceptional, (137 reviews)
"The place was very clean, and the host was was communicative and helpful. "
United States
Steven & Vicki S.
The price is CA $105
CA $353 total
includes taxes & fees
May 4 - May 5
Water View - optional BIKES - Walk 2 Pier Village

Beach Square 3 –optional BIKES – Walk 2 Redfern Village, shops, and restaurants!

Beach Square 3 –optional BIKES – Walk 2 Redfern Village, shops, and restaurants!
Saint Simons Heights
10.0 out of 10, Exceptional, (1 review)
"Property was awesome and very clean. "
United States
Josh R.
The price is CA $81
CA $305 total
includes taxes & fees
May 3 - May 4
Beach Square 3 –optional BIKES – Walk 2 Redfern Village, shops, and restaurants!

The Sea Gate

The Sea Gate
4.0 star property
St. Simons Island
9.6 out of 10, Exceptional, (613 reviews)
"Layout was good. Very large bathroom"
United States
Hunter
The price is CA $244
CA $456 total
includes taxes & fees
Apr 30 - May 1
The Sea Gate

Abundant Amenities! Pool, Bikes, Near to beach!

Abundant Amenities! Pool, Bikes, Near to beach!
Saint Simons Island
9.8 out of 10, Exceptional, (165 reviews)
"Host was welcoming and amenities were great. Location was also great."
United States
Randy and Jackie P.
The price is CA $122
CA $512 total
includes taxes & fees
May 17 - May 18
Abundant Amenities! Pool, Bikes, Near to beach!

Summer Special! Steps to Village & Pier

Summer Special! Steps to Village & Pier
St. Simons Island
9.2 out of 10, Wonderful, (26 reviews)
"Great communication from host, very clean place, great neighborhood, perfect location!"
United States
natalie h.
The price is CA $168
CA $475 total
includes taxes & fees
May 4 - May 5
Summer Special! Steps to Village & Pier
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windward Acres. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Windward Acres?

Yes, we offer vacation rentals in Windward Acres close to Captain Scott Owens, or you can select a more secluded option if you want a relaxing stay.

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

Big Luxury Island Style 5 Bed 3 Bath One level Sleeps 9 Quiet Street GR8 Locati: This vacation home rental outside of Windward Acres offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

What can I see and do in Windward Acres?

Explore the area and family-friendly sights such as Captain Scott Owens, or get out into nature at a spot like Sea Island Beach. 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.