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Windward Acres Vacation Rentals

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Our top choices for Windward Acres vacation rentals

1. Ocean Lodge Resort

Ocean Lodge Resort
4.0 star property
St. Simons Island
8.4 out of 10, Very good, (430 reviews)
"Very attentive staff and the rooftop bar was amazing"
United States
Sean
The price is CA $143
CA $234 total
includes taxes & fees
Nov 10 - Nov 11
Ocean Lodge Resort

2. #Butterfly to the Beach just 16 min. to nearest Beach #Sleeps up to 8 guests!

#Butterfly to the Beach just 16 min. to nearest Beach #Sleeps up to 8 guests!
Brunswick
9.4 out of 10, Exceptional, (57 reviews)
"Had a great time, the community was quiet, and it is close enough to Jekyll Island for fun and sun! Would stay again."
United States
Rachel P.
The price is CA $126
CA $368 total
includes taxes & fees
Nov 9 - Nov 10
#Butterfly to the Beach just 16 min. to nearest Beach #Sleeps up to 8 guests!

3. The Sea Gate

The Sea Gate
4.0 star property
St. Simons Island
9.6 out of 10, Exceptional, (639 reviews)
"This was one of the best places we have stayed on St. SIMON island.. such a beautiful and CLEAN villa. It was worth the money. It also was personal, quiet, and comfortable. The location was perfect. We will return next year!"
United States
Nicole
The price is CA $202
CA $439 total
includes taxes & fees
Nov 8 - Nov 9
The Sea Gate

4. Little Live Oak Cottage 1-bedroom cottage on Saint Simons

Little Live Oak Cottage 1-bedroom cottage on Saint Simons
Saint Simons Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great place for short weekend, felt like home and the hosts were very inviting."
United States
John B.
The price is CA $175
CA $279 total
includes taxes & fees
Nov 18 - Nov 19
Little Live Oak Cottage 1-bedroom cottage on Saint Simons

5. La Vie Insulaire -optional BIKES

La Vie Insulaire -optional BIKES
Saint Simons Heights
9.8 out of 10, Exceptional, (28 reviews)
"Great location and ideal for our family trip."
United States
V
The price is CA $30
CA $248 total
includes taxes & fees
Nov 19 - Nov 20
La Vie Insulaire -optional BIKES

6. Beach Square 3 -optional BIKES-Pool-Walk 2 Redfern

Beach Square 3 -optional BIKES-Pool-Walk 2 Redfern
Saint Simons Heights
9.8 out of 10, Exceptional, (8 reviews)
"Property was awesome and very clean. "
United States
Josh R.
The price is CA $30
CA $248 total
includes taxes & fees
Nov 19 - Nov 20
Beach Square 3 -optional BIKES-Pool-Walk 2 Redfern

7. 💥Gated community 🌟3 bedroom 🧘🏽Serenity & Comfort⚡️

💥Gated community 🌟3 bedroom 🧘🏽Serenity & Comfort⚡️
Brunswick
10.0 out of 10, Exceptional, (18 reviews)
"Very convenient location, beautiful townhouse, clean, safe, restaurants nearby, great host."
United States
Glori B.
The price is CA $208
CA $449 total
includes taxes & fees
Nov 8 - Nov 9
💥Gated community 🌟3 bedroom 🧘🏽Serenity & Comfort⚡️

8. Direct Marshlands Views + Golf. Pool. Restaurant.

Direct Marshlands Views + Golf. Pool. Restaurant.
St. Simons Island
9.6 out of 10, Exceptional, (4 reviews)
"Very welcoming, beau beautifully appointed. Breathtaking view of the marshes and a screened in porch. One of my favorite things in the world is a screened-in porch. The wall to wall carpeting, the linens and the mattress, all of the appointments just say luxury. The dogs and I had a couple of nice walks around the grounds. Wish we had more time to stay there."
United States
Laura D.
The price is CA $187
CA $300 total
includes taxes & fees
Nov 29 - Nov 30
Direct Marshlands Views + Golf. Pool. Restaurant.

9. 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, (134 reviews)
"The accommodations were very good and clean"
United States
Brenda
The price is CA $30
CA $208 total
includes taxes & fees
Nov 22 - Nov 23
Beach Cottage -optional BIKES - Walk 2 Shops & Fun

10. Villas By the Sea Resort & Conference Center

Villas By the Sea Resort & Conference Center
3.0 star property
Jekyll Island
8.4 out of 10, Very good, (1,177 reviews)
"Really enjoyed our stay."
United States
Don
The price is CA $183
CA $254 total
includes taxes & fees
Nov 9 - Nov 10
Villas By the Sea Resort & Conference Center

11. Beach GO BO-HO

Beach GO BO-HO
3.5 star property
Brunswick
7.4 out of 10, Good, (3 reviews)
"The owner was wonderful, the room was beautiful and the bed was heavenly. Will definitely be back again."
United States
Antinette
The price is CA $63
CA $107 total
includes taxes & fees
Nov 11 - Nov 12
Beach GO BO-HO

12. 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, (159 reviews)
"The property was clean and convenient to restaurants, shopping, and the beach. I would definitely stay here again!"
United States
Sharon T.
The price is CA $30
CA $244 total
includes taxes & fees
Nov 8 - Nov 9
Beach Air -optional BIKES-Pool-Walk 2 Pier Village

13. ✅Tranquil & cozy 🌟3 bedroom⚡️Wi-Fi 🔥Gated Community

✅Tranquil & cozy 🌟3 bedroom⚡️Wi-Fi 🔥Gated Community
Brunswick
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay in Georgia. The house felt like the perfect home away from home. "
United States
Neuza
The price is CA $208
CA $449 total
includes taxes & fees
Nov 8 - Nov 9
✅Tranquil & cozy 🌟3 bedroom⚡️Wi-Fi 🔥Gated Community

14. Pet-Friendly St. Simons Island Townhouse | Near Beach | Fall & Winter Getaway *Snowbirds welcome*

Pet-Friendly St. Simons Island Townhouse | Near Beach | Fall & Winter Getaway *Snowbirds welcome*
Saint Simons Island
9.6 out of 10, Exceptional, (18 reviews)
"Condo was a great location. We enjoyed our stay and would love to come back."
United States
Julia R.
The price is CA $124
CA $648 total
includes taxes & fees
Nov 8 - Nov 9
Pet-Friendly St. Simons Island Townhouse | Near Beach | Fall & Winter Getaway *Snowbirds welcome*

15. 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, (155 reviews)
"Very clean and Property Manager was friendly andattentive. We had a great time staying thereLiked: cleanliness, check-in, communicationlocation, listing accuracy, value for money"
United States
Debra J.
The price is CA $93
CA $317 total
includes taxes & fees
Nov 10 - Nov 11
Beach House -optional BIKES - Walk 2 Shops & Fun

16. Sandy Toes. Cozy 2 Bedroom 2 Full bath. Sleeps 6. 30 day rental rates available

Sandy Toes. Cozy 2 Bedroom 2 Full bath. Sleeps 6. 30 day rental rates available
Saint Simons Heights
10.0 out of 10, Exceptional, (9 reviews)
"The apartment looked exactly like the pictures. We had a wonderful weekend."
United States
Alicia
The price is CA $159
CA $477 total
includes taxes & fees
Nov 8 - Nov 9
Sandy Toes. Cozy 2 Bedroom 2 Full bath. Sleeps 6. 30 day rental rates available

17. NEW LISTING! Sea Palms Golf Course Home | 3BR St. Simons Island Vacation Rental

NEW LISTING! Sea Palms Golf Course Home | 3BR St. Simons Island Vacation Rental
Saint Simons Island
10.0 out of 10, Exceptional, (1 review)
"Great location on the golf course"
United States
Sean M.
The price is CA $167
CA $821 total
includes taxes & fees
Nov 16 - Nov 17
NEW LISTING! Sea Palms Golf Course Home | 3BR St. Simons Island Vacation Rental

18. 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, (161 reviews)
"Great location. "
United States
Katie S.
The price is CA $30
CA $239 total
includes taxes & fees
Nov 8 - Nov 9
Beach Walk -optional BIKES-Pool-Walk 2 PierVillage

19. 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 $100
CA $240 total
includes taxes & fees
Nov 9 - Nov 10
Tiny House 20 Mins from Beach

20. Demere House Condo #2 | Walk-to-Beach 2BR St. Simons Island Vacation Rental Near Pier Village

Demere House Condo #2 | Walk-to-Beach 2BR St. Simons Island Vacation Rental Near Pier Village
St. Simons
9.6 out of 10, Exceptional, (20 reviews)
"Location is 100% on point. We couldn't ask for a better location. The unit is spacious and the beds were comfortable. One parking spot with some parking for visitors. Walking distance to downtown and public beach areas."
United States
David
The price is CA $137
CA $665 total
includes taxes & fees
Nov 8 - Nov 9
Demere House Condo #2 | Walk-to-Beach 2BR St. Simons Island Vacation Rental Near Pier Village
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 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?

Beach House -optional BIKES - Walk 2 Shops & Fun: This vacation home rental outside of Windward Acres has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 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.