Vacation rentals with a pool in Hilton Head

4.98 out of 5 average rating, 109 reviews

New Resort-Style Pool, Cute House 88 Steps to Sand

Experience the best of island life in a resort-style setting. Recently renovated, this classic home offers comfortable living by a MAGNIFICENT beach for a memorable family-friends getaway. 1st floor features a screened in porch; open living-dining area; a well stocked kitchen; three bedrooms (3rd bedroom with separate hallway) and two bathrooms. The new private pool space is where you can expect additional relaxation around pool, cabana with dining area, KitchenAid grill and outdoor seating.

A spacious kitchen featuring sleek white cabinetry and a large marble island with seating for four. Modern appliances, including a stainless steel refrigerator and oven, are visible, along with a stylish black backsplash that complements the overall design.

4.95 out of 5 average rating, 88 reviews

Luxe Hilton Head Beach Villa w/ Pool Views

Escape to our beautiful beach getaway where you are just a short walking distance to a beautiful natural beach. Our completely restored condo is designed with the perfect blend of luxury and relaxation to enjoy your time in Hilton Head. Our spacious and open floor plan creates a bright and an inviting atmosphere that is perfect for lounging with loved ones and friends. Our bedrooms will give you a perfect night of rest and relaxation while each bathroom provides the perfect spa like experience

4.95 out of 5 average rating, 119 reviews

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. (2) King BRs, 3rd BR with (2) Queens. Flat screen TVs, cable, ROKU in all bedrooms. Doorbell cam viewing fromt porch and driveway with recording capability. Beach access @ Omni resort and the Dunes House is a 5-10 min ride by bike and a 15 min walk. Beach towels/umbrellas/chairs not provided. Pool/spa heat extra fee

4.94 out of 5 average rating, 140 reviews

Cottage in Tybee Island

Salty Mermaid: Private Pool/Hot Tub, Walk to Beach

Make a splash in your own PRIVATE HEATABLE LAGOON POOL and hot tub at The Salty Mermaid Cottage, voted the swankiest coastal charmer on Tybee! Relax in this unique 1940s retreat that's full of mermaid whimsy and cheery colors by Lilly Pulitzer. Your personal paradise is very close to the beach yet away from the crowds. Whether strolling Tybee’s beaches or exploring the island or Savannah, GA, rest easy on our relaxing screened-in porch w/ our 2 cozy swing beds. Book now to find your oasis!

Superhost

5 out of 5 average rating, 3 reviews

37 Bradley Cir, Private Pool, Free Golf, Beach

37 Bradley Circle, Hilton Head Island, is a four bedroom, three bathroom home nestled in a quiet beach area of Burkes Beach. Step inside to the main level, where you'll find a cozy living room, large TV and access to the upper dining deck. The fully-equipped kitchen, complete with stainless steel appliances and granite countertops, sets the stage for memorable culinary experiences. Recently updated with the vacationer in mind, this home offers ample space for everyone to relax and unwind.

A swimming pool is surrounded by loungers for relaxation. Palm trees adorn the area, providing shade. A fountain is centered in the pool, creating a tranquil atmosphere. The neighboring building offers a sense of privacy and is partially visible in the background.

4.97 out of 5 average rating, 118 reviews

Oceanfront Breathtaking Views

Gorgeous Ocean front views await your perfect vacation at this beautifully decorated beach condo in Palmetto Dunes. Five star rated condo features lush landscaping, palm trees, and tropical flowers will entice your senses. Amenities nearby, swimming pools, barbecue grill, hot tub, white sandy beaches, bike cruisers, kayak, pickle ball, golf, fishing and tennis await you. Your condo features a spacious 1 bedroom, 2 bathrooms , kitchen, dining, living room, and balcony for your comfort .

Top guest favorite

A screened-in pool area features a clear blue pool surrounded by light-colored tiles. Comfortable lounge chairs are arranged nearby, and a dining set is positioned under a ceiling fan. A television is mounted on the wall for entertainment.

4.98 out of 5 average rating, 109 reviews

Cozy beach house w/Private Heated Pool near park

Short walk to Singleton beach or Burkes beach. This oversized 4 bedroom 4 ensuite is the perfect retreat close to everything the Island has to offer. The home features a screened in pool with TV and adjacent ping pong table. The open concept living space is perfect for entertaining with access to a large porch and grill. The property is steps away from Chaplin Park that hosts Tennis, Playground, Soccer, Baseball, Basketball, Trails and Fields for the kids to play. Sleeps 12.

A large outdoor pool is surrounded by numerous lounge chairs and features a spacious area for swimming. People are enjoying the water under a clear blue sky, with grassy areas and shaded cabanas in the background, along with the condo buildings lining the edge.

4.89 out of 5 average rating, 205 reviews

Oceanside Beach Retreat

Modern Beach Condo with Ocean View Located in Hilton Head Beach and Tennis Resort Short walking distance to beach, pool side bar (Jamaica Joe's), and the beachfront pool Family friendly resort (playground, bike rentals, weekly activities) First Floor Condo Recently renovated One bedroom and one full bath Sleeps 6 people (2 bunk beds and pull out couch) Full kitchen (dishwasher, microwave, stove, coffee maker, dishes) Balcony with table and 2 chairs 2 public pools located on pr

Top guest favorite

The image displays Villamare Villas, a complex set amidst lush greenery, with an expansive sandy beach in the foreground. The calm ocean waves create a soothing backdrop, while several visitors can be seen strolling along the shore under a clear blue sky.

5 out of 5 average rating, 20 reviews

Voted #1 Beach in the USA 2 new pools and hot tubs

5 Star Rating⭐️⭐️⭐️⭐️⭐️ Close to everything when you stay at our centrally-located condo. Steps from the Beach! Steps from the Pool! A fun and clean place to stay! 11-mile lagoon for kayaking, fishing. 5 miles of paved bike paths in Palmetto Dunes and Shelter 50 more miles of paths that surround and Island. 3 legend built golf courses. Robert Trent Jones, The George Fazio, Arthur Hills 24 dedicated Pickleball courts. 17 clay tennis courts. A wonderful place to be!

Superhost

4.95 out of 5 average rating, 131 reviews

Stylish, Renovated Coastal Haven on Hilton Head!

Beautifully decorated condo on one of the most tranquil, serene, and natural beaches on on the island! Be prepared to take in amazing sunsets and sunrises. Open floor plan overlooking the pool. All appliances, fixtures, and furnishings are brand new and everything upgraded!! Master bathroom is absolutely gorgeous! Striking navy blue tile paired with white tiles and matte black fixtures. This villa offers modern and sophisticated charm in a casual coastal setting!

Vacation home in Hilton Head Island

The exterior of a spacious home is presented, surrounded by lush greenery and tall trees. A private pool glistens in the sunlight, with comfortable lounge chairs positioned nearby. The structure features varied rooflines and large windows, providing an inviting atmosphere.

4.92 out of 5 average rating, 64 reviews

Summer Bliss: Family home, Pool, Golf, Beach, 14+

You’ve found it! The perfect vacation home in central Hilton Head! We are located in Sea Pines on the 11th hole at Heron Point for the ultimate Hilton Head experience. Golfers’ getaways, multi-generation family groups, friends reunions – will all enjoy the ample gathering areas and huge kitchen. With five bedrooms, including a bunk room, guests can recharge in relaxing private spaces. While enjoying the outdoors, take advantage of the private, heated pool and hot tub.

Top guest favorite