List your Property
Calibogue Cay, Hilton Head Island, South Carolina, United States of America

Calibogue Cay vacation rentals

We found 234 vacation rentals — enter your dates for availability

Discover a selection of 234 vacation rentals in Calibogue Cay, Hilton Head Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $95 per night, and villas and houses are popular options for a stay in Calibogue Cay. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style

Villas

View 98 Villas

Houses

View 165 Houses

Condos/Apartments

View 65 Condos/Apartments

Find the best place to stay — Calibogue Cay

3 Minute Drive to Beach at this 1 Bedroom Harbour Town Condo with Lagoon Views

Sleeps 4 · 1 Bedroom · 1 Bathroom
$103 avg/night
(41)

Work,Stay,Play...PrvtHomeDeerIsl,2Bdrm2Bth,FastFreeWifi,SlfEntry,LrgDeck,HrbrTwn

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$160 avg/night
(74)

Racquet Club Villas - Overlooking Golf Course, Pool and Tennis Courts!

Sleeps 4 · 1 Bedroom · 1 Bathroom
$120 avg/night
(76)

RENOVATED Sealoft on one of a kind Deer Island

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$185 avg/night
(39)

Harbor Town Fantastic Panoramic Water View of Calibogue Bay

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$200 avg/night
(56)

New Listing! Stunning Sea Pines Treetop Oasis w/ Deck & Grill, Near Beach

Sleeps 4 · 1 Bedroom · 1 Bathroom
$114 avg/night
(24)

Search 234 vacation rentals

Top rated rentals — Calibogue Cay
Stayed Jun 2021

Relaxing Sea Pines stay

This condo was fantastic. Loved all the natural light in the unit, and the location sandwiched between Harbortown and the Beach Club. A totally central spot within Sea Pines. We made great use of the pool at Inland Harbor and enjoyed morning walks to...

Carrie L.
Carrie L.

Charlotte, NC

Stayed Jun 2021

Excellent spot to vacation

My husband and I booked this condo for our honeymoon and we were very happy with it. Walking distance to shops and restaurants, but also all the amenities to cook in the condo if you dont want to eat out for every meal. Porch overlooked a nice golf c...

Caitlin L.
Caitlin L.
Stayed May 2021

Hiltonhead Golf!

The property was true to the description. Dennis was very responsive to my questions prior and during the stay. The kitchen is well appointed; however, we did not cook. Harbortown shops and resturants are just a short walk away with outdoor entertain...

Teresa B.
Teresa B.
Stayed May 2021

Will come back again!

As others have mentioned, this place is exactly as advertised. The place is clean, well furnished(even some condiments in the fridge) and close to everything. Many times, with places near water, there is a smell in the apartment/condo. Not in this on...

Sylvain D.
Sylvain D.
Stayed May 2021

Location Location Location

Perfect location…. Just sit and watch the world go by… coffee on a morning or a cold beer in the evening. The apartment was fabulous and just as advertised. We had to get in touch with Turnkey when we arrived as there were 2 minor issues but they re...

Michelle H.
Michelle H.

Georgia USA

Stayed May 2021

Memorial Day Getaway

Absolutely loved the location of this property! We walked and biked all over Sea Pines, took the trolley to the Beach Club & the pool at South Beach Marina. Home is beautifully decorated and the deck is just incredible! Great views of the sunrise, ...

Adrienne J.
Adrienne J.
Stayed May 2021

Great location, well stocked, but has mold issues

I thought it was great, but these things really need to be addressed before you rent this place. The entire place has a very strong musty/moldy smell throughout. There is standing water in basement with mold growing. There is high humidity in the pla...

Tara C.
Tara C.
Stayed May 2021

Peaceful retreat

Perfect spot for our anniversary getaway. So quiet, breezy and peaceful up in the trees. Could accommodate a couple with 2 kids if the kids are small & the adults can share a double bed. This is remote from most of the island and we rented bikes so i...

Melissa P.
Melissa P.
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many vacation rentals are available around Calibogue Cay, Hilton Head Island?

Our 2021 property listings offer a large selection of 234 vacation rentals around Calibogue Cay. From 98 villa rentals to 165 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Villas in Calibogue Cay?

Yes, of course. Vrbo has 98 Villas in Calibogue Cay. Our other popular types of vacation rentals in Calibogue Cay include:

  • Houses: 165 rentals available
  • Condos/Apartments: 65 rentals available
  • Townhouses: 6 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.

Can I find a vacation rental with pool in Calibogue Cay?

Yes, you can select your preferred vacation rental with pool among our 178 vacation rentals with pool available in Calibogue Cay. Please use our search bar to access the selection of vacation rentals available.