Vacation rentals with a pool in Hilton Head Island

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.

Top guest favorite

4.95 out of 5 average rating, 205 reviews

2bed/2ba ~Sleeps 7 ~ KING Bed ~ Restaurants ~CLEAN

Fully Furnished, Renovated Non-Smoking Villa sleeps 7 - King bed in Master, 2 Single beds in Guest Room, Leather Queen Sofa Bed & Rollaway Bed. Built-in Bar, Fully-equipped Kitchen w/ small appliances. Beach Chairs, toys, games, cards. Flat Screen HDTV w/ hundreds of channels, DVD, Free Wi-Fi. Overhead Lighting & Ceiling fans in bdrms, extra blankets & pillows. Restaurants, Tennis, 2 Pools. Sip cold drinks on the wide sandy beach & watch Amazing Sunrises & Sunsets. Relax, You're in Paradise

An outdoor pool is surrounded by landscaped grounds, featuring lounge chairs positioned around the edges. A small gazebo is visible in the background, with tall trees providing shade nearby. The pool depth is indicated, showing a gradual slope with a shallow area marked at 3 feet.

4.85 out of 5 average rating, 111 reviews

Modern villa for vacation or remote work getaway!

Recently renovated 2 bedroom/2 bath villa with large balcony! This second story unit of a waterfront complex is a 3-minute walk to the beach off of Port Royal Sound. Guests can access 2 outdoor pools, a hot tub, 1 indoor pool, sauna, gym, tennis courts, and multiple grilling areas. Located in a quiet, beautifully landscaped part of Hilton Head island. Rental is equipped with high-speed wifi and perfectly set up for remote work! Cable, a wet bar, and a fully stocked kitchen are also provided.

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

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 .

4.85 out of 5 average rating, 123 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Beautiful home located in Palmetto Dunes Resort. Deck with pool overlooking the first tee of Fazio Golf course with fantastic views of the sunset. Carolina room makes a great 5th bedroom. Private Cul-De-Sac street. Short walk to the beach, general store and tennis center. Enjoy all the amenities of the resort including its beaches, three golf courses, fishing, kayaking, tennis, pickleball, bike trails, restaurants and Dunes Buggy shuttle. Perfect for family beach trips or golf getaways.

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, 108 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

Apartment in Hilton Head Island

The outdoor heated pool is surrounded by palm trees, providing a tranquil setting. Comfortable lounge chairs are positioned along the pool's edge, inviting relaxation. A nearby shaded area suggests space for unwinding, with clear blue skies enhancing the serene atmosphere.

4.85 out of 5 average rating, 219 reviews

Priceless Ocean View, King Bed, Heated Pool

Enjoy the best beach on Hilton Head Island during your stay in our newly renovated condominium in Ocean Dunes with a year round heated pool. You can relax in the comfortable surroundings our condo offers. Begin your day with a breathtaking view of the sunrise from the balcony or enjoy your meals on the balcony relaxing with your favorite beverage while you enjoy the beach view. *Please note: A printed parking pass is required for your stay. Be sure to print it in advance.*

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!

A well-maintained outdoor pool is surrounded by lounge chairs, with the sun setting in the background. Lush trees provide shade, and the nearby condominium can be seen in the background, enhancing the tranquil atmosphere of the area.