Harbor Island vacation rentals

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Top-rated vacation rentals in Harbor Island

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Guest favorite

Guesthouse in Beaufort

4.96 out of 5 average rating, 208 reviews

Sunset River House

Our quaint little River House rests on the beautifully natural marsh grass banks of the Whale Branch River in a quiet rural neighborhood. It is located only 9 miles from Historic Downtown Beaufort and 15 miles from Parris Island Marine Corps Recruit Depot. Hunting Island State Park's sandy beaches, nature tails, and lighthouse tours are a scenic 40 minute drive away. You can swim, fish, kayak or go boating right from the dock in our own back yard. When you arrive; you won't want to leave!

Dec 22 – 29

G$22,319 GYD per night

Guest favorite

Cottage in Beaufort

4.95 out of 5 average rating, 215 reviews

Cara May Cottage

We love the laidback neighborhood, charming historic architecture, and the 5-block walk to the breezy waterfront along Bay Street. The cozy cottage is one bedroom, one bath, and a lovely living space on a postage stamp lot. The built-in breakfast nook is our favorite spot. Other features are the chic furnishings, 11’ ceilings, tall casement windows, and little front porch. Off-street private parking for one car and smart tv/wifi. The 400 SF cottage is named after the architect's daughter.

Oct 17 – 24

G$33,453 GYD per night

Guest favorite

Condo in Saint Helena Island

4.97 out of 5 average rating, 112 reviews

La Sirena , First Floor Ocean View 1 BR Villa

First floor 1 bedroom with 1.5 baths. Located in a gated community on Harbor Island. The island has 3 miles of sandy beach which is just steps away. Views of the ocean & pool can be seen from the screened-in porch. Enjoy 3 pools, tennis, basketball , pickle ball courts, full gym access. Dog park located at the BRC.We also offer a free pass for Hunting Island State Park to use during your stay. We do have golf cart and bike rentals on the Island. Please see pictures for info. Relax and Enjoy!

Sep 20 – 27

G$39,260 GYD per night

Guest favorite

Guesthouse in Beaufort

4.96 out of 5 average rating, 198 reviews

Spacious Carriage House with Pool & King Bed

Forget your worries in this serene space. Located on 5-acres of secluded wooded land with extensive gardens. This quiet space is on the second floor above a detached garage. The spacious area has just been refurbished: includes a kitchenette and bathroom. Private entry through gated courtyard. Central HVAC; new King bed and TV; Private pool exclusively for guests. LGBTQ welcome. Driving times: 25 min. to Hunting Is. St. Park and Parris Island; 15 min. to historic downtown Beaufort.

Feb 8 – 15

G$23,857 GYD per night

Guest favorite

Guesthouse in Bluffton

5.0 out of 5 average rating, 442 reviews

Lowcountry Retreat Carriage House

Located in a quiet neighborhood, minutes from Old Town Bluffton, where you can find unique shops, art galleries, & great places to eat - many with live music! A stroll through the neighborhood will take you past a local park with playground, workout area, & walking paths. There are many ponds to enjoy the local wildlife, wetland areas, and beautiful oak trees. It's so peaceful! Convenient to Hilton Head, Beaufort, and Savannah, it's the perfect spot for exploring, shopping, or relaxing!

Sep 9 – 16

G$26,107 GYD per night

Guest favorite

Guesthouse in Saint Helena Island

4.99 out of 5 average rating, 187 reviews

Charming Waterfront Cottage with Beautiful Views.

This is a very comfortable guest cottage with one bedroom, bathroom with large shower, kitchenette, and living room. Guests will occasionally share the dock, screened-in porch, and swimming pool. "MarshSong" is an inspirational place for anyone who just wants to relax, or explore; a good central point for visiting Charleston and Savannah. A beach pass is provided for Hunting Island State Park as well as beach chairs and towels. Rest, relax, recharge - nap on a hanging bed; sleep well.

Aug 26 – Sep 2

G$36,015 GYD per night

Guest favorite

Guesthouse in Beaufort

4.98 out of 5 average rating, 435 reviews

Peace Point

Come and enjoy Peace Point's beautiful views of the Broad River and huge oak trees with the Spanish moss. It is just a walk away from the Broad River fishing pier which showcases beautiful sunsets! It is also just minutes away from Parris Island & MCAS. Peace Point is a private guest house with a king size bed and queen sofa sleeper with an amazingly comfortable Tempurpedic mattress.The guesthouse has a beachy vibe with calming colors. It has a small freezer/fridge and microwave.

Oct 22 – 29

G$22,001 GYD per night

Guest favorite

Guesthouse in Beaufort

4.98 out of 5 average rating, 196 reviews

Buddy's Cottage near everything in Beaufort, SC

Who is Buddy? He was our black Labrador of 12 years. You'll see his photo as you enter. This brand new guest cottage has a private bedroom, 1 full bathroom, a sleeper sofa , 2 TV's, a full kitchen and all the amenities of home. Downtown Beaufort is 2 miles away, Parris Island is less than 5 miles away. In a quiet neighborhood. Are coming for a fishing trip and bringing your boat? Come stay with us , we have room for your boat. You can flush your engine and rinse your boat down.

Aug 27 – Sep 3

G$27,028 GYD per night

Guest favorite

Cottage in Saint Helena Island

4.99 out of 5 average rating, 199 reviews

Harbor River Cottage

Romantic cottage on three-acres surrounded by gorgeous South Carolina waterways with endless views on all sides! Cottage is BRAND NEW with a dog-friendly, fully-fenced front yard and screened-in porch. Full kitchen, private parking, washer & dryer, 55" TV with DirecTV. A short 5-10 minute drive from Hunting Island State Park, Downtown Beaufort and all the major attractions. Cottage is beautifully furnished with custom pieces to make this your ultimate low country luxury getaway!

Oct 7 – 14

G$38,181 GYD per night

Guest favorite

Home in Saint Helena Island

4.99 out of 5 average rating, 108 reviews

The Hampton House

CUSTOM BEACHFRONT HOME ON GORGEOUS LOW COUNTRY BEACH. VIEWS VIEWS! Custom beachfront home with unparalleled views! Beautifully but comfortably decorated in low country beach style. All the comforts of home. Feels like your own private paradise. 4 bed 3 1/2 bath,Sleeps 12 with TWO King master en suites. Stainless Steel Kitchen, private boardwalk to the beach, Golf Cart, Kayaks, beach towels, chairs, umbrellas, 2 car passes... all included. Make memories that will last forever.

Sep 15 – 22

G$179,342 GYD per night

Guest favorite

Apartment in Fripp Island

4.91 out of 5 average rating, 314 reviews

Fripp Island Dog Friendly Getaway OPEN ALL WINTER

325 sq. ft. studio efficiency offers a central island location just 1 min. from the beach! Bed arrangements: 2 TEMPURPEDIC mattresses, one queen size bed/one full size sleeper sofa. Ideal for 2 but will sleep 4 very snugly. *Our affordable rates are in part because "amenity cards" may not be purchased and are not available by any means with this unit Cards are necessary to use restaurants/bars/pools/tennis & golf. * **Check out our 2nd pet friendly unit at 530 Sunsuite!

Oct 30 – Nov 6

G$26,002 GYD per night

Guest favorite

Condo in Saint Helena Island

4.91 out of 5 average rating, 115 reviews

Frippin’ Fun Vacation - Fripp Island

Relax and enjoy your FRIPPIN' FUN VACATION on the beautiful Fripp Island located in South Carolina. This stunning 1 bed / 1 bath condo is located on the Third Floor with beautiful marsh and canal views and breathtaking sunset views. This condo is in the heart of the Island and is just a short walk to the Beach Access. Perfect for couples and solo adventures. Featuring an updated space and beach themed decor, this space is perfect to relax in after a day at the beach.

Oct 12 – 19

G$36,778 GYD per night