Vacation rentals with a pool in Hilton Head Island

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Top-rated rentals with a pool in Hilton Head Island

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Guest favorite

Home in Hilton Head Island

4.98 out of 5 average rating, 107 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.

Guest favorite

Condo in Hilton Head Island

4.91 out of 5 average rating, 213 reviews

Gorgeous views-Close to beach, Resort Amenities!

Hear the sounds of the ocean from this 2 BD, 2BA Oceanside condo in Hilton Head Resort! Private beach access from this Building 1 villa-closest building to the beach & steps to the pool! Spectacular views of lagoon, tidal marsh leading to ocean & palmetto dunes golf course from your private terrace. Best of all, a short walk to the beach via our private boardwalk. Located mid island with great amenities-Indoor heated pool, hot tub & tennis. Close to supermarket, Shelter Cove shops & restaurants.

Superhost

Condo in Hilton Head Island

4.84 out of 5 average rating, 109 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.

Guest favorite

Condo in Hilton Head Island

4.94 out of 5 average rating, 196 reviews

$69/nt -Jan weekdays- BEACH -Sleeps 5 -KING -CLEAN

Fully Furnished, Renovated Non-Smoking Villa sleeps 5 w/ King bed in Master, 2 Single beds in Guest Room & Rollaway Bed. Built-in Bar, Fully-equipped Kitchen with all small appliances. Beach Chairs, beach toys, games, cards. Flat Screen HDTV with hundreds of cable 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 and watch Amazing Sunrises & Sunsets. Relax, You're in Paradise.

Guest favorite

Condo in Hilton Head Island

4.96 out of 5 average rating, 111 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 .

Superhost

Home in Hilton Head Island

4.86 out of 5 average rating, 120 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.

Guest favorite

Home in Hilton Head Island

4.98 out of 5 average rating, 103 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.

Guest favorite

Home in Hilton Head Island

4.95 out of 5 average rating, 117 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 10-15 min walk. NOTE: Beach towels/umbrellas/chairs not provided.

Superhost

Apartment in Hilton Head Island

4.85 out of 5 average rating, 216 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.*

Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 122 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!

Superhost

Condo in Hilton Head Island

4.75 out of 5 average rating, 137 reviews

Beautiful Top Floor Pool View Villa

This condo is located on the 4th floor in highly coveted building 1 overlooking the pool from the balcony. It is only a short 7 minute stroll, or 1 minute beach shuttle ride (in season) on our private boardwalk over a serene salt water marsh to the beach. The walk is so beautiful we even have places to sit and enjoy. The villa has all the convenience of home, complete with everything you will need for a relaxing weekend or extended stay.