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

4.85 out of 5 average rating, 229 reviews

End unit w lovely ocean view @ HHBT

*4/22/2021 Brand new bath & kitchen with convection microwave, LVP flooring, lighting, fixtures, furniture, mattress, everything from curtains to bedding & Samsung smartTV. Our end unit offers amazing 360 views of the ocean & resort from our front & rear balconies! We're so proud to share our new space with you. We wanted to keep the vintage vibe of the villa while adding all the luxury and modern comforts you expect while traveling and relaxing in style. *2-3 guest max. No pets. 25 age minimum*

Superhost

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, 258 reviews

Ocean View & Steps to beach! Remodeled HHBT Condo

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, 189 reviews

Super Low Rates - 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, 239 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, 267 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, 246 reviews

Coastal King Beach Flat Convenient to Everything!

Incredible location right on the beach! Walking distance to Coligny Plaza where there are a multitude of restaurants, cafe's, cute shops, bike rental places everything you need. Quite complex with pool and sundeck. High speed internet WIFI, smart tvs, Roku & Cable. All of the comforts of home including fully stocked kitchen, comfortable King bed, great for remote working, updated. Many extra amenities including beach chairs, umbrellas, water/soft drinks, Coffee K-cups, cooler, & essentials.

Guest favorite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 312 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

4.86 out of 5 average rating, 103 reviews

Time to BEACH! Oceanview 1B/1B Condo at HHBT

Newly updated 1 bedroom/1 bathroom Oceanview Condo located at Hilton Head Bach & Tennis Resort. Three restaurants onsite, beach side pool, playground, grilling areas, gym, bike rentals and more! Always something fun to do on the island. From enjoying the beach to bike riding, your vacation will not disappoint. Minute walk from the beach. Your rental also includes Netflix, Disney +, Prime Video and TV entertainment on all 4 condo TV's. We are always available to answer any questions.

Guest favorite

Condo in Hilton Head Island

4.98 out of 5 average rating, 150 reviews

"Beach Time" - a cozy HHI Condo, steps from beach

10/26-31 available. Low fees! Ninja tent & Solbello sunshade. HHI Beach & Tennis is a beachfront resort with many vacation amenities. Our condo is on first floor of OV B, close to the pool and beach activities but far away enough from noise of pool and restaurant. Our condo is 2-3 minutes from the beach. We provide a clean, safe, comfortable and affordable space for our guests. Our condo is cleaned, sanitized and ozonized. We have an air system, air purifier and dehumidifier.

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**