Windmill Harbor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windmill Harbor vacation rentals

Hilton Head Condo: Beach Supplies, Walk to Shore!

Hilton Head Condo: Beach Supplies, Walk to Shore!
3.0 star property
Mid Island
8.0 out of 10, Very good, (4 reviews)
"I’m thrilled with the location of this condo. It’s just a quick walk to the beach, and there are also easy-to-access walking, running, and biking trails. There are plenty of local restaurants, food trucks, grocery stores, and attractions nearby. The only downside is that I didn’t receive the email from Evolve with the check-in/out instructions, as it was delivered to my spam folder. The unit was a bit dusty, probably because it was the off-season when I visited, but a quick trip to the local...
United States
Derval
The price is CA $88
CA $434 total
includes taxes & fees
Apr 20 - Apr 21
Hilton Head Condo: Beach Supplies, Walk to Shore!

Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (197 reviews)
"Very clean room and resort "
United States
Larisa
The price is CA $817
CA $899 total
includes taxes & fees
Apr 22 - Apr 23
Marriott's SurfWatch

DeSoto Beach Gardens

DeSoto Beach Gardens
2.5 star property
South Beach
8.4 out of 10, Very good, (229 reviews)
"Cute little one bedroom. Check in person was very curt. The maintenance person was more helpful to us."
United States
Ashley
The price is CA $306
CA $367 total
includes taxes & fees
Apr 20 - Apr 21
DeSoto Beach Gardens

Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (67 reviews)
"Another great Marriott, super clean and spacious with the comforts we needed to finish out a long trip (e.g. hot tub, laundry, kitchen). Friendly staff and convenient to the forest reserve."
United States
Landry
The price is CA $505
CA $556 total
includes taxes & fees
May 8 - May 9
Marriott's Heritage Club

Montage Palmetto Bluff Residences

Montage Palmetto Bluff Residences
5.0 star property
Palmetto Bluff
10.0 out of 10, Exceptional, (1 review)
"This was our second visit to Montage Palmetto Bluff and once again it did not disappoint. The hospitality we find here is second to none. Everywhere we went we were greeted with smiling faces. We’d like to give a special shout out to Carmela at the concierge desk who was so incredibly wonderful with our 4 year-old son, Henry. Everything she did and every recommendation she provided enhanced our stay. The natural beauty of this place is beyond compare. We cannot wait to visit again. "
United States
Ashley
The price is CA $2,143
CA $2,548 total
includes taxes & fees
May 17 - May 18
Montage Palmetto Bluff Residences

Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (128 reviews)
"While the rooms are overdue a refurbishment, this place is a wondeful resort. "
United States
Chad
Disney's Hilton Head Island Resort

Desoto Beach Terraces

Desoto Beach Terraces
3.0 star property
South Beach
8.6 out of 10, Excellent, (117 reviews)
"Easy walk to the beach and with the best ocean view possible. "
United States
April
The price is CA $374
CA $446 total
includes taxes & fees
May 4 - May 5
Desoto Beach Terraces

Walk to Bars & Shops: Resort Condo in Hilton Head!

Walk to Bars & Shops: Resort Condo in Hilton Head!
3.5 star property
South End
The price is CA $101
CA $467 total
includes taxes & fees
Apr 28 - Apr 29
Walk to Bars & Shops: Resort Condo in Hilton Head!

Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (173 reviews)
"Very clean room, warm pools, excellent location! "
United States
Sean
The price is CA $905
CA $996 total
includes taxes & fees
Apr 22 - Apr 23
Marriott's Grande Ocean

Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (63 reviews)
"We are vacation club owner and we extended our stay with Hotels.com Harbor Club is our favorite property on HHI. "
United States
Mark
The price is CA $466
CA $512 total
includes taxes & fees
Apr 22 - Apr 23
Marriott's Harbour Club

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Breakers 137 Condo w/ Sunrise Views!
3.5 star property
South End
Oceanfront Breakers 137 Condo w/ Sunrise Views!

Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (250 reviews)
"Beautiful property "
United States
Charlotte
The price is CA $812
CA $893 total
includes taxes & fees
Apr 22 - Apr 23
Marriott's Barony Beach Club

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Marriott's Harbour Point and Sunset Pointe at Shelter Cove
3.5 star property
Mid Island
9.2 out of 10, Wonderful, (150 reviews)
"Very nice place to stay "
United States
Alejandro
The price is CA $394
CA $434 total
includes taxes & fees
Apr 22 - Apr 23
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

1 Mi to River! Relaxing Family Home in Bluffton

1 Mi to River! Relaxing Family Home in Bluffton
3.0 star property
Bluffton
The price is CA $329
CA $959 total
includes taxes & fees
May 3 - May 4
1 Mi to River! Relaxing Family Home in Bluffton

'wright by the Beach': Hilton Head Condo w/ Perks

'wright by the Beach': Hilton Head Condo w/ Perks
3.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay. We loved the ocean theme at the apartment. Very clean rooms. Kids enjoyed swimming in the indoor pool, parents enjoyed hot tub and sauna especially on rainy days. They have indoor and outdoor pools. We liked walking on the boardwalk to the beach. We highly recommend this place and would love to return there again. "
United States
Victor
'wright by the Beach': Hilton Head Condo w/ Perks

Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!

Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!
3.0 star property
Edgefield
10.0 out of 10, Exceptional, (1 review)
"It was like home away frim home. "
United States
Willie
The price is CA $235
CA $708 total
includes taxes & fees
May 14 - May 15
Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!

Marriott's Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (132 reviews)
"Loved this property "
United States
Sharon
The price is CA $737
CA $810 total
includes taxes & fees
May 1 - May 2
Marriott's Monarch at Sea Pines

2 Mi to Beach! Hilton Head Golf Escape w/ Balcony

2 Mi to Beach! Hilton Head Golf Escape w/ Balcony
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (2 reviews)
"We have stayed at several properties, and this one did not disappoint. Everything was just as described if not better. Had a little trouble finding it and called and was given directions immediately, after that it was amazing. We will definitely stay here next year. Thanks for a great experience 😊"
United States
Grace
The price is CA $156
CA $630 total
includes taxes & fees
May 7 - May 8
2 Mi to Beach! Hilton Head Golf Escape w/ Balcony

Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
9.0 out of 10, Wonderful, (4 reviews)
"Nice!! Location great, easy instructions on entry access, nice side view of the ocean from the balcony, the host Meagan was so very nice and accommodating, very close to restaurants and stores, would love to stay here again, Thanks a million!!!! ;)"
United States
Beverly
The price is CA $168
CA $504 total
includes taxes & fees
May 1 - May 2
Oceanfront Hilton Head Island Condo w/ Pool!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windmill Harbor Hotel Reviews

Find out more about Windmill Harbor

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 Windmill Harbor. 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 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 Shelter Cove Harbour and Tanger Outlets 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.