Vacation rentals with a pool in Hilton Head

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Top-rated rentals with a pool in Hilton Head

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

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Guest favorite

Condo in Hilton Head Island

4.89 out of 5 average rating, 178 reviews

Hilton Head Hidden Gem

Comfy 3rd floor walk up retreat. Peaceful decor. Screened balcony. Furnished kitchen. Free use of WIFI, beach chairs/umbrella, gym, basketball & tennis courts, charcoal grills/picnic tables; pools. Steps from your door: explore our sandy beach, watch fish jump & dolphins swim; observe nature on a private pier. See the sunrise on the water. Grocery/restaurants w/in 1-5 miles. Make a meal or a reservation! Short drive to all island locales. Great island bike paths. (No pets or smoking.)

Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 260 reviews

Ocean View! Remodeled HHBT Condo -steps to beach

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

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

Condo in Hilton Head Island

4.96 out of 5 average rating, 241 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your private balcony. Private beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!

Guest favorite

Condo in Hilton Head Island

4.94 out of 5 average rating, 124 reviews

Beach resort, pools, tennis, pickle ball, tiki bar

2 bed/2 bath condo includes full kitchen with S.S. appliances, dining area, hardwoods throughout & balcony overlooking the 6 lit tennis courts. The resort also features a deli & gift shop, 2 outdoor pools, 1 year-round inside heated pool (great for winter), running track, fitness, hot tub, sauna, elevators, golf nearby & laundry facilities. The beach is a 7+ min stroll down a board walk or during operational hours take the shuttle. At the beach you can stop into Coco's for lunch & cold drinks.

Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 268 reviews

Ocean Front Resort Villa

Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much more.

Guest favorite

Condo in Hilton Head Island

4.98 out of 5 average rating, 100 reviews

First-floor resort condo with private beach access

Welcome to the beach! Enjoy private beach access from Fiddler’s Cove, a gated beach & racquet club with 2 pools, a hot tub, tennis & pickleball. This newly renovated 2-bed / 2-bath condo is on the first floor closest to the beach. It has everything: new appliances, quartz countertops, a fully stocked kitchen, in-unit laundry, a 75” TV in the living room, 55” TVs in bedrooms, and tons of beach equipment, including a cart, umbrellas, toys & more. Plus, upgraded 250 MB Internet & no cleaning fee!

Guest favorite

Condo in Hilton Head Island

4.9 out of 5 average rating, 163 reviews

Beachfront property with ocean/sunrise view!

Ocean sunrises from your private balcony! Steps to the beach! Newly renovated 1 Bed/1 Bath villa in a gated ocean community. New flooring throughout with new central air/heat. Nicely appointed, fully equipped and immaculate. Perfect for up to 4 guests. Boardwalk to beach. Outdoor pool/showers. 2 beach cruiser bicycles included. Easy walk to Coligny Plaza for many restaurants, shops, grocery, etc. Great golf courses, tennis, biking/hiking trails, boating/fishing, parks in area.

Guest favorite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 314 reviews

LOCATION! Harbour, Dining, Shops, Beach-1.4 mile

Location .. Location .. Location !!! Private guest suite (256 sq ft) with independent entrance from outside, total privacy, and complete amenities, queen bed and full bath (no kitchen). Just step outside - great water-front restaurants with live music, bars, shops and weekly fireworks during summer. Supermarkets and more restaurants in 10 minutes walking. Free shuttle to attractions in 2 miles radius from April till September, beach 1.4 miles away, biking, fishing and water sports.

Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 182 reviews

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Welcome to our renovated 2BR 2BA Villa at Hilton Head Beach & Tennis Resort. It is a short walk to the Resort's beautiful Private Access Beach and largest outdoor pool on the Island Updated appliances, furniture & bathrooms. Villa has a fully equipped Kitchen, Coffee Bar with Keurig, Memory Foam Mattresses on all Beds 3 Wall Mounted Smart TV's Hi Speed Wifi. Sleeps 5 adults Comfortably contact us for info on add'l guests. Porta Crib supplied but guest must bring own linens for crib

Guest favorite

Condo in Hilton Head Island

4.99 out of 5 average rating, 125 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 258 reviews

Walk to Beach+Coligny+Pool + Dining #Location

Newly updated Sands Village condo one block from the beach. Enjoy your vacation with updated furnishings, new furniture, cotton sheets, and organic/nature-oriented decor. This condo has a cute balcony that overlooks the pool; a great place to kick back and relax, have a drink or read a book. You're only one block from the beach and just steps from from Coligny Plaza that hosts a grocery store, bakery, ice cream shop, restaurants, coffee shop, and many other gift shops.