Windmill Harbor Vacation Rentals from CA $134: Short-Term Rentals for 2026

Q: 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.

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

A covered outdoor seating area with a view of the sunset over a body of water.

1. Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Mid Island

Gary T

CA $134 total

includes taxes & fees

Dec 3 - Dec 4

A spacious living area with a high ceiling, large windows, and a central seating arrangement.

2. Marriott's Heritage Club

Sea Pines

Christine

CA $197 total

includes taxes & fees

Dec 2 - Dec 3

A beachside resort with a swimming pool, lounge chairs, and a small building, likely a lifeguard station.

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

Mid Island

Dora D.

CA $440 total

includes taxes & fees

Nov 7 - Nov 8

A swimming pool with multiple lanes and lounge chairs, surrounded by a fenced area and buildings in the background.

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

Mid Island

Shawn K.

CA $338 total

includes taxes & fees

Nov 10 - Nov 11

A compact living space with a kitchenette, a sofa, a coffee table, and a balcony with a view.

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

South End

Sherri P.

CA $368 total

includes taxes & fees

Nov 7 - Nov 8

A balcony with a table and chairs, overlooking a landscaped garden and distant hills.

6. Oceanfront Hilton Head Island Condo w/ Pool!

South End

Beverly

CA $419 total

includes taxes & fees

Nov 10 - Nov 11

A waterfront hotel with multiple red-roofed buildings, a dock, and a marina.

7. Disney's Hilton Head Island Resort

Mid Island

Melissa

A courtyard with a central water feature, surrounded by brick flooring and benches.

8. Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380

South End

Will K.

CA $413 total

includes taxes & fees

Nov 10 - Nov 11

A view of a beach with a parking lot and buildings in the foreground.

9. Castaways King Villa on Beach, Free Bikes!

South End

Kathleen

CA $383 total

includes taxes & fees

Nov 7 - Nov 8

A modern kitchen with white cabinets, a central island with stools, a dining area with a sofa and cushions, and a ceiling fan.

10. Adorably furnished and updated Ocean Villa condo, with wonderful 200+ Reviews!

Mid Island

Whitney K.

CA $444 total

includes taxes & fees

Dec 1 - Dec 2

A hotel room with a balcony, a dining area, and a seating area with a view of the ocean.

11. Marriott's Monarch at Sea Pines

Sea Pines

Cory

CA $220 total

includes taxes & fees

Dec 6 - Dec 7

12. Flip Flop Paradise-Steps to the Sand! Free Bikes

South End

Linda P.

CA $376 total

includes taxes & fees

Nov 7 - Nov 8

A room with a sliding glass door leading to an outdoor patio with a table and chairs, a ceiling fan, and a flat-screen TV mounted on the wall.

13. SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

South End

Beth T.

CA $383 total

includes taxes & fees

Nov 7 - Nov 8

14. SunnyDaze-Brand new reno- King bed, Free bikes!

South End

Jake H.

CA $374 total

includes taxes & fees

Nov 7 - Nov 8

A multi-story building with balconies, surrounded by various tropical plants and a clear view of the ocean.

15. Beach Daze-Gorgeous new shower! Bikes Included

South End

Kathleen

CA $376 total

includes taxes & fees

Nov 7 - Nov 8

A living room with a dining area, a sofa, a coffee table, and a TV.

16. Harbour Town Gem: Serene Lagoon Views & Steps to the Lighthouse

Sea Pines

Matt K.

CA $418 total

includes taxes & fees

Nov 10 - Nov 11

A covered outdoor area with a view of the sea, featuring a railing and a pathway.

17. Sunset Dunes Direct Beach Access

South End

Celeste G.

CA $383 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living room with a gray sofa, ottoman, and patterned rug. A ceiling fan and an air conditioning unit are visible.

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

Old Town Bluffton

Derek

CA $381 total

includes taxes & fees

Nov 10 - Nov 11

A modern building with a view of the ocean.

19. Good Times and Tan Lines!-Central air, free bikes!

South End

Griffith S.

CA $383 total

includes taxes & fees

Nov 8 - Nov 9

A multi-story residential building with a central courtyard, outdoor seating area, and a pool.

20. Lagoon View Resort Villa - Walk to the Beach!

Mid Island

meredith l.

CA $496 total

includes taxes & fees

Nov 7 - Nov 8

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Top Windmill Harbor Hotel Reviews

Red Roof Inn Hardeeville

10/10 Excellent

"incredible value"

Beach House Resort Hilton Head

8/10 Good

"Great place and excellent location, but unfortunately, our experience was disappointing due to the lack of attention from staff and security. We stayed in an ocean-view room on the fourth floor. The property had clearly posted no-smoking signs and designated smoking areas, with hefty fines for violations. Despite this, cigarette smoke repeatedly came into our room whenever we opened the sliding door. After investigating, we strongly suspected the guests directly above us were smoking. We reported this to the front desk multiple times, but they insisted the smoke was coming from the designated smoking area near the bar. We explained that we continued smelling it even after the bar had closed. Security came to our room, and we specifically told them where we believed it was coming from. Again, they blamed the bartender rather than properly investigating. The following morning, we saw the guests above us smoking, confirming exactly what we had been reporting. Had security simply taken the time to investigate, this could have been resolved. The lack of follow-through and basic due diligence was extremely frustrating. It affected our enjoyment of the stay, as we couldn't leave our sliding door open and enjoy the ocean air without cigarette smoke filling our room. It's a shame because the property and location are great. Management needs to take its smoking policies seriously and ensure staff and security actually enforce them."

Hotel Tybee

8/10 Good

"Cost to stay was outrageous. Room view was nice. Could not afford to eat on site prices really high. Maybe for the cost of the room they would include at least a breakfast. Staff was excellent. I forgot my iPhone charger would be really cool if y’all could mail that back to me. Also the safe in the room did not work again for the cost of the room. It should have a working safe."

Extended Stay America Premier Suites Bluffton Hilton Head

8/10 Good

"Front desk lady was nice. The room wasn't stocked with items you would expect for an extended stay. Had to ask for a hair dryer, a pot to boil water in. Kitchen isn't stocked with any utensils, no coffee pot no plastic wear etc. Found a dead roach under the cabinet."

Royal Palms Motel

8/10 Good

"Our stay was just fine for what we needed. Plenty of room which I loved. Especially 2 bathrooms so the kids had their own. Not much water pressure and the water would turn cold sometimes during shower. On the morning we were leaving we did see a roach on the couch. The floors are warped and unlevel. Unappealing on the outside but the inside looks much different. Cute little retro decor. Parking is slim."

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windmill Harbor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windmill Harbor vacation rentals we have selected for you start as low as CA $134 per night. Entering your travel dates in the search wizard 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.

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Check prices for these dates

Our top choices for Windmill Harbor vacation rentals

1. Marriott's Harbour Point and Sunset Pointe at Shelter Cove

2. Marriott's Heritage Club

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

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

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

6. Oceanfront Hilton Head Island Condo w/ Pool!

7. Disney's Hilton Head Island Resort

8. Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380

9. Castaways King Villa on Beach, Free Bikes!

10. Adorably furnished and updated Ocean Villa condo, with wonderful 200+ Reviews!

11. Marriott's Monarch at Sea Pines

12. Flip Flop Paradise-Steps to the Sand! Free Bikes

13. SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

14. SunnyDaze-Brand new reno- King bed, Free bikes!

15. Beach Daze-Gorgeous new shower! Bikes Included

16. Harbour Town Gem: Serene Lagoon Views & Steps to the Lighthouse

17. Sunset Dunes Direct Beach Access

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

19. Good Times and Tan Lines!-Central air, free bikes!

20. Lagoon View Resort Villa - Walk to the Beach!

Find vacation rentals that suit your style

Top Windmill Harbor Hotel Reviews

Red Roof Inn Hardeeville

Beach House Resort Hilton Head

Omni Hilton Head Oceanfront Resort

Tru by Hilton Beaufort, SC

Spark By Hilton Hilton Head Island

Admiral's Inn on Tybee Island

Hotel Tybee

Extended Stay America Premier Suites Bluffton Hilton Head

Royal Palms Motel

Find out more about Windmill Harbor

Frequently asked questions

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