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Windmill Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windmill Harbor vacation rentals

A covered outdoor area with a pool, lounge chairs, and a sofa.

1. Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (202 reviews)
"Great resort, great room "
United States
Crista
$194 nightly
The price is $213
Dec 1 - Dec 2
Total with taxes and fees
Marriott's SurfWatch
A spacious living area with a high ceiling, large windows, and a central seating arrangement.

2. Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (71 reviews)
"Great Villa! Very roomy and excellent location close to everything!"
United States
Christine
$111 nightly
The price is $122
Dec 2 - Dec 3
Total with taxes and fees
Marriott's Heritage Club
A waterfront restaurant with outdoor seating and a view of the water.

3. Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (131 reviews)
"The room and property were incredible! Already booking my next stay"
United States
Melissa
$166 nightly
The price is $183
Nov 5 - Nov 6
Total with taxes and fees
Disney's Hilton Head Island Resort
A beachside resort with a swimming pool, lounge chairs, and a small building, likely a lifeguard station.

4. Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
Mid Island
9.6 out of 10, Exceptional, (120 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
$275 nightly
The price is $303
Nov 7 - Nov 8
Total with taxes and fees
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
A narrow courtyard with a palm tree, a chair, and a small table.

5. DeSoto Beach Gardens

DeSoto Beach Gardens
2.5 star property
South Beach
8.4 out of 10, Very good, (245 reviews)
"Nice suite with a short walk to the beach."
United States
Kimberly
$146 nightly
The price is $172
Nov 2 - Nov 3
Total with taxes and fees
DeSoto Beach Gardens
A wide flat walkway to beach.

6. At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.

At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.
Mid Island
10.0 out of 10, Exceptional, (155 reviews)
"Cozy condo that was perfect for our stay."
United States
Shawn K.
$220 nightly
The price is $242
Nov 5 - Nov 6
Total with taxes and fees
At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.
A sandy beach with blue umbrellas and lounge chairs.

7. STUNNING ocean view! Brand new listing

STUNNING ocean view! Brand new listing
South End
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely loved our stay would recommend"
United States
xiaoming w.
$232 nightly
The price is $255
Nov 2 - Nov 3
Total with taxes and fees
STUNNING ocean view! Brand new listing
A beach scene with tall grasses in the foreground and the sun setting over the ocean.

8. Ocean View Condo - Perfect location! 2 BR 2 BA

Ocean View Condo - Perfect location! 2 BR 2 BA
Mid Island
9.8 out of 10, Exceptional, (109 reviews)
"Great location and amazing view! We loved our stay!"
United States
Elizabeth K.
$328 nightly
The price is $361
Nov 2 - Nov 3
Total with taxes and fees
Ocean View Condo - Perfect location! 2 BR 2 BA
Beach

9. Seas the Day! Beach & Sun, with Bikes & Chairs

Seas the Day! Beach & Sun, with Bikes & Chairs
South End
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay."
United States
Robert
$239 nightly
The price is $262
Nov 2 - Nov 3
Total with taxes and fees
Seas the Day! Beach & Sun, with Bikes & Chairs
A balcony with wicker furniture, overlooking a beach with tall trees and a clear sky.

10. Beautiful Couples Retreat Oceanview w/new bikes&Chairs

Beautiful Couples Retreat Oceanview w/new bikes&Chairs
South End
9.8 out of 10, Exceptional, (137 reviews)
"Gated community with free parking and direct beach access."
United States
Debra
$248 nightly
The price is $273
Nov 2 - Nov 3
Total with taxes and fees
Beautiful Couples Retreat Oceanview w/new bikes&Chairs
A wooden boardwalk leading to a beach with a bicycle parked on it.

11. Marriott's Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (133 reviews)
"After a booking mixup on what Expedia had listed & what the property details were.. we were happily surprised that the staff & GM made an exception for our reservation. Everyone was very helpful, room was great, clean, great outdoor spaces & easy beach access."
United States
Cory
$146 nightly
The price is $161
Dec 2 - Dec 3
Total with taxes and fees
Marriott's Monarch at Sea Pines
A colonial-style house with a brick chimney, surrounded by azaleas and large trees with Spanish moss.

12. Old Town Bluffton Cottage | Pet-Friendly, Big Yard

Old Town Bluffton Cottage | Pet-Friendly, Big Yard
Old Town Bluffton
9.4 out of 10, Exceptional, (148 reviews)
"This is a perfect little long weekend get away retreat! Very clean, close to everything walking distance to shops restaurants the river and parks. The bed was extremely comfortable. We were in town for a family reunion and had family that were staying close by it was the perfect spot to gather a visit. We will definitely book again next year for the union."
United States
Eric
$296 nightly
The price is $328
Nov 2 - Nov 3
Total with taxes and fees
Old Town Bluffton Cottage | Pet-Friendly, Big Yard
A beach with a wooden fence, sand, and grass.

13. Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!

Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!
Old Town Bluffton
9.8 out of 10, Exceptional, (99 reviews)
"Excellent location, very clean, will definitely repeat"
United States
Sean m.
$390 nightly
The price is $404
Nov 2 - Nov 3
Total with taxes and fees
Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!
A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

14. Gorgeous 5 ⭐️ custom home! 5 king suites! FREE Spa Heat, Easy 5min walk to beach

Gorgeous 5 ⭐️ custom home! 5 king suites! FREE Spa Heat, Easy 5min walk to beach
Mid Island
10.0 out of 10, Exceptional, (119 reviews)
"Great house for large groups. All 5 couples were able to have a King bedroom with private walk in shower. House was clean and as described. Great location to get anywhere on the island."
United States
Jason K.
$1,227 nightly
The price is $1,350
Nov 7 - Nov 8
Total with taxes and fees
Gorgeous 5 ⭐️ custom home! 5 king suites! FREE Spa Heat, Easy 5min walk to beach
A courtyard with a central fountain, surrounded by palm trees and a large tree in the background.

15. Coligny Beach, Pools, & Shops- Few Steps Away

Coligny Beach, Pools, & Shops- Few Steps Away
South End
9.6 out of 10, Exceptional, (98 reviews)
"The place is immaculate and the location is excellent."
United States
Margarita
$302 nightly
The price is $332
Dec 1 - Dec 2
Total with taxes and fees
Coligny Beach, Pools, & Shops- Few Steps Away
A beach with sand dunes, a wooden fence, and a clear blue sky.

16. Beachy chic, steps from the beach!

Beachy chic, steps from the beach!
Mid Island
9.4 out of 10, Exceptional, (71 reviews)
"We had a lovely stay here. A great place for a couple. The property manager was very helpful too."
United States
Sarah D.
$287 nightly
The price is $316
Nov 2 - Nov 3
Total with taxes and fees
Beachy chic, steps from the beach!
A spacious living room with a gray sofa, ottoman, and patterned rug. A ceiling fan and an air conditioning unit are visible.

17. Carriage House within 5 minute walk of Old Town Bluffton

Carriage House within 5 minute walk of Old Town Bluffton
Old Town Bluffton
10.0 out of 10, Exceptional, (100 reviews)
"Very clean, and very convenient location. Host was great and communicated perfectly. We will definitely stay again."
United States
Derek
$248 nightly
The price is $272
Nov 2 - Nov 3
Total with taxes and fees
Carriage House within 5 minute walk of Old Town Bluffton
A deck with sun loungers overlooking a natural landscape.

18. Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views
South End
9.4 out of 10, Exceptional, (87 reviews)
"Everything was perfect from location, cleanliness, and communication with the host"
United States
Victor A.
$256 nightly
The price is $282
Nov 2 - Nov 3
Total with taxes and fees
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views
Beach

19. Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
South End
9.6 out of 10, Exceptional, (43 reviews)
"You truly are steps to the beach and can see the water from the balcony. This place was so close to shopping and dining. Excellent place to stay!"
United States
Sherri P.
$239 nightly
The price is $262
Nov 2 - Nov 3
Total with taxes and fees
Feelin Tip'Sea-Oceanview Retreat Steps to Beach
A modern kitchen with a built-in refrigerator, microwave, and coffee maker. There is a dining area with a wooden table and chairs, and a living room with a sofa and a window with curtains.

20. C & N Lodging, Bluffton, SC

C & N Lodging, Bluffton, SC
Bluffton
9.8 out of 10, Exceptional, (12 reviews)
"Extremely clean and very well kept. Perfect for what we were looking for. Price was very affordable, awesome stay!!!"
United States
Maggie M.
$202 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
C & N Lodging, Bluffton, SC
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 Windmill Harbor Hotel Reviews

Holiday Inn Express Hilton Head Island by IHG

Holiday Inn Express Hilton Head Island by IHG

10/10 Excellent
"."
Cheryl 4-night trip
Posted 5 hours ago
Holiday Inn Express Hilton Head Island by IHG

Find out more about Windmill Harbor

Everything you need to know about Windmill Harbor 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 Windmill Harbor 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 Windmill Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windmill Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windmill Harbor. 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 Windmill Harbor 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 $140 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 Windmill Harbor rentals

At Expedia, we put the best Windmill Harbor 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 Windmill Harbor 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 Windmill Harbor 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 Windmill Harbor. 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 Windmill Harbor?

Yes, we offer vacation rentals close to the most popular attractions in Windmill Harbor, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Windmill Harbor has to offer?

Desoto Beach Terraces: This vacation home rental near Windmill Harbor is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a terrace and an arcade game room.

What can I see and do in Windmill Harbor?

While exploring the area, visit family-friendly sights like Coastal Discovery Museum, or get outside and enjoy nature at Sea Pines Forest Preserve. In the larger area, you’ll find Marine Corps Recruit Depot Parris Island and Country Club of Hilton Head.

What are vacation rentals like in Windmill Harbor?

Vacation rentals are private accommodations you can book for several days or more in Windmill Harbor. Vacation rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.