Vacation rentals with a pool in Hilton Head Island

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Top-rated rentals with a pool in Hilton Head Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Hilton Head Island

4.98 out of 5 average rating, 106 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, 212 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, 108 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

4.89 out of 5 average rating, 104 reviews

Upgraded peaceful villa ! 7 min walk to the beach

- 757 sq ft condo on the 2nd floor - Key-less entry - 7 minutes walk to the beach via private access - Two pools (warmed in the winter and cooled in the summer) - Two hot tubs - Tennis & racket ball courts free to use - TV in each bedroom and living room with cable and Roku - Playground in front of the condo - Community center with corn hole, ping pong tables and more - Fully stocked and equipped kitchen - Baby crib and toys available - Extremely safe gated community with 24/7 controlled access

Guest favorite

Condo in Hilton Head Island

4.94 out of 5 average rating, 190 reviews

$89/nt -Dec 3-20 -VERY CLEAN -KING Bed -Sleeps 5 -

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

Home in Hilton Head Island

4.95 out of 5 average rating, 116 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 (NO HEAT). 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 ARE NOT PROVIDED

Superhost

Home in Hilton Head Island

4.9 out of 5 average rating, 128 reviews

Family Gem ~ FREE Heated Pool ~ Walk to Beach~BBQ

Step into the spacious and fun 6BR 4Bath family oasis nestled in a tranquil neighborhood just a few steps away from pristine sandy beaches, restaurants, and exciting attractions. Explore the island from this prime location or lounge the day away next to the luxury swimming pool. ✔ 6 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Patio (Heated Pool, Fire Pit, BBQ) ✔ Deck ✔ Games (Beer Pong, Cornhole) Arcade ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Beach Accessories ✔ Parking See more below!

Guest favorite

Condo in Hilton Head Island

4.96 out of 5 average rating, 110 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

4.85 out of 5 average rating, 117 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, 102 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

Condo in Hilton Head Island

4.95 out of 5 average rating, 121 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.