Discover a selection of 431 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 $89 per night, and houses and villas are popular options for a stay in Calibogue Cay. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Calibogue Cay
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What are the top vacation rentals in or near Calibogue Cay?

Whatever your getaway needs, you'll find a rental in or around Calibogue Cay that fits you like a glove. These are some of our favorites:

  • "Castle By The Sea 7br/8ba Luxury Home With Elevator" is a guest favorite. Around 3 miles from Calibogue Cay, it has 7 bedrooms and loads of amenities to help you feel at home, including outdoor furniture and a heated pool.
  • Alternatively, unpack your bags at "9 Wisteria Ln - 1 Level Renovated Home". Located around 1 mile from the heart of Calibogue Cay, it has 2 bedrooms and comes with outdoor furniture and a nearby beach.

For even more great options, use the search bar at the top of the page to find the perfect Calibogue Cay vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Calibogue Cay?

Clock out on Friday and then forget all about work. If you're chasing some fun and relaxation, these properties in and around Calibogue Cay promise an amazing weekend getaway:

  • Leave the hustle and bustle behind at "2 Min Walk 2 Beach, Pvt Heated Pool", which is around 5 miles to the east of central Calibogue Cay. There's plenty of nature and adventure on your doorstep here. Go parasailing and windsurfing or just explore the sights of Savannah NWR Visitor Center and Henry C. Chambers Waterfront Park.
  • Alternatively, leave your troubles behind at "Make Memories : Book 1916 Sbc, Stunning Views". Use it as a base to relax, or head out for some parasailing and fishing. When it's time to explore more of the area, check out Oyster Bay Golf Club and The Legends at Parris Island. This charming vacation rental is around 2 miles southwest of Calibogue Cay.

Can I find studio apartments for rent in and around Calibogue Cay?

Studio apartments may be small in size, but they pack a punch when it comes to convenience and location. Unpack your bags and settle into one of these cozy studio apartments in and around Calibogue Cay:

  • One of our favorite picks is "Experience Luxury At The Beach Oceanside Resort Huge Oceanside Pool". Book a few nights or longer at this popular abode and you'll have access to internet services and nearby birdwatching activities.
  • "Great Amenities, Clean, Convenient" is another terrific choice, offering all you could want for the perfect Calibogue Cay escape. Handy amenities here include tennis and free WiFi.

Can I find short term rentals in or near Calibogue Cay?

Every so often, you just need to get away from it all, even if it's only for two or three days. Enjoy a pleasant mix of relaxing and exploring at one of these short-term rentals in or around Calibogue Cay:

  • If you'd like to be near the action, "5 Star Ratings - Ocean View - South Beach Marina" will be just the ticket. It's within reach of the heart of Calibogue Cay and a good base to explore attractions like Coligny Beach and Harbour Town Lighthouse.
  • "Spectacular Home With Brand New Pool In Harbour Town January Specials" is another wonderful option. We recommend adding Coligny Plaza and Hilton Head Island Beaches to your must-do list when you're ready to sightsee.

What are the best romantic weekend getaways in or near Calibogue Cay?

Forget about roses and chocolates. Sometimes all you need is to take off for the weekend, just you and your boo. At Vrbo, we've got romantic getaways in and around Calibogue Cay that would make even old Cupid swoon. Here are some we think you'll fall hard for:

  • Put on some love songs and slow dance the nights away at "Castle By The Sea 7br/8ba Luxury Home With Elevator". Around 3 miles from Calibogue Cay, this property has everything you could want for a romantic weekend away, including a dining table and a restaurant dining guide.
  • Alternatively, spend your escape sipping wine and canoodling at "9 Wisteria Ln - 1 Level Renovated Home", around 1 mile from Calibogue Cay. A resort and shopping facilities will help set the mood for romance.

What are the best large group vacation rentals in or near Calibogue Cay?

Big groups mean enormous fun. They also mean finding someplace that'll comfortably fit your entire gang. Check out our large group vacation rentals in or around Calibogue Cay and get your favorite people together under one roof:

  • Providing space, comfort and privacy, you'll get everyone's stamp of approval at "Castle By The Sea 7br/8ba Luxury Home With Elevator". Up to 18 people can stay at this escape which has 7 bedrooms, a kitchen and a swimming pool. This top pick is around 3 miles to the east of Calibogue Cay.
  • Nothing's more important than spending time with the people you love, and "2 Min Walk 2 Beach, Pvt Heated Pool" is the perfect place to do that. Located around 5 miles to the east of Calibogue Cay, as many as 12 guests can stay in this vacation rental which has 5 bedrooms. A swimming pool and a fireplace are among the many amenities you'll have at hand.

What are the best houses for rent with a pool in or near Calibogue Cay?

Having access to a swimming space is always a nice perk when you're on vacation, especially if you're bringing the kids. Stay and splash the days away at one of these houses with a pool in or near Calibogue Cay:

  • Toss your swimsuit in your suitcase and enjoy a fun stay at "Great Beach House - 2 Min. Walk To Beach". Other amenities here include a fridge and a microwave oven.
  • Alternatively, make a reservation at "Sea Pines Deer Island Tree House With Ocean Views" and spend your break poolside. Towels and a barbecue grill are other things your gang will love about this vacation home.

What are the best large family vacation rentals in or near Calibogue Cay?

Whether your ideal getaway is up in the mountains or by the beach, you'll have so much more fun if you share it with family and friends. Choose one of these large family vacation rentals in or near Calibogue Cay and bring the whole gang:

  • Located about 3 miles to the east of Calibogue Cay, "Castle By The Sea 7br/8ba Luxury Home With Elevator" has 7 bedrooms and sleeps up to 18 guests. It comes with lots of amenities, including a fenced pool and cable/satellite TV services.
  • "2 Min Walk 2 Beach, Pvt Heated Pool" also offers the space you need to share special moments with loved ones. This property is around 5 miles to the east of central Calibogue Cay and accommodates 12 guests in its 5 bedrooms. A dishwasher and a stereo will help keep everyone happy and comfortable.

If you're hoping to visit some family-friendly attractions in the area, you won't have to go far. The Sandbox, Adventure Cove and Coligny Theater promise lots of fun for both adults and kids.

What are the best large houses to rent with indoor pools in or near Calibogue Cay?

Add a serve of grandeur to your getaway by booking somewhere with a private indoor pool. These amazing large houses in or near Calibogue Cay have a swimming space that's all your own, along with lots of room for whoever is fortunate enough to be coming with you:

  • With 3 bedrooms that can fit up to 8 guests, "Ultimate In Luxury And Location, Steps From Beach" is the perfect place to reconnect with the people that matter most. Take advantage of this retreat's host of amenities, such as a swimming pool and a kitchen.
  • Another awesome option is "3201 Seacrest - 3 Bedroom Premier Direct Ocean Front Villa". With 3 bedrooms accommodating up to 10 people, you can invite the whole gang to stay, play and swim. A beach view and a swimming pool are other amenities you'll find here.

Use the search bar at the top of the page and adjust the filters to find more outstanding Calibogue Cay vacation rental options for your next big getaway.

Are there one-bedroom vacation rentals in or near Calibogue Cay?

Absolutely. You'll find many one-bedroom vacation rentals in or near Calibogue Cay. If space is not a priority, one of these popular properties is sure to be a perfect fit:

  • Check into "316 Breakers - Direct Ocean Front" for a weekend. This one-bedroom vacation property features a kitchen and a swimming pool and is not far from downtown.
  • Also within easy reach of all the delights of Calibogue Cay, "315 Breakers Direct Oceanfront Condo" is another popular one-bedroom option. After a big day of seeing the sights, come home and enjoy a swimming pool and an ocean view.