
Vacation rentals with a pool in Hilton Head Island
Find and book unique homes with a pool on Airbnb
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.

Luxury Oceanfront! KING BED 65"TV Pickleball & BAR
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR!! Beachfront Balcony ✨Top 1% of Airbnb✨ Beachfront Pool, Bar & Grille FREE Pickleball, Tennis, Gym, Vollyball & More HGTV Decorator Renovation KING BED + Two 65" SmartTVs Spa Bath w/Walk-in Shower Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESSORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Sports Bar Gated 24/7 Security Seasonal IslandTrolley Stop Bradley Beach

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!

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.

Desirable Oceanfront Resort*End Unit*Bikes/Chairs
Charming villa with everything you need for the perfect beach getaway- just steps from the sand! Elevated 1st floor, END UNIT offers lots of natural light and ramp for easy access. Situated in desirable C building, closest to beach, pool and Jamaica Joe'z restaurant/ tiki bar. 2 FREE bikes, chairs & beach towels! HHBT Resort provides gated security and countless amenities, including the island's largest oceanfront pool, multiple restaurants/ bars, tennis courts, playgrounds & fitness center.

Oceanfront Villa on Hilton Head Island!
This one bedroom, one bath oceanfront Villa is a third floor end unit that sleeps 5. There’s an adjustable queen bed, a set of bunk beds (Intended for children) and a twin sleeper sofa. It is a three minute walk to the sandy shores of Hilton Head Island. The gated resort has these amenities: two pools (one of which is the largest beach front pool on the island), 10 tennis courts, pickle ball courts, fitness center, bike rental, playground, and three restaurants. Reserve your vacation today!

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 balcony. Natural 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!a

Ocean front condo with amazing ocean view!
Ocean front condo with amazing view of the ocean and beach from balcony. You are just steps to the beach. In addition, you will be within walking distance to Coligny Plaza with many great restaurants and shops. Guests get to enjoy the onsite pool, sun deck, and grilling area. Luggage carts are located by the pool and elevator to easily transport all your luggage to the condo. Fast upgraded wifi for streaming and work needs. No pets allowed. Preapproval required for service animals.

BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN
Freshly decorated in coastal decor, this beachfront condo sleeps up to 4 and is located right by Coligny, Hilton Head's chicest neighborhood. Freshly furnished unit includes a spacious king bed and queen sofa sleeper, both fitted with luxurious memory foam mattresses. Just a three minute walk to sandy beaches, and you can catch a glimpse of gentle tides from your own private balcony! The villa is full of amenities including beach chairs, beach umbrella, games and much more.

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**

Ocean Views at Villamare, Steps to the Beach!
Read our reviews! We strive to provide an unforgettable Hilton Head experience in our renovated villa with ocean views, comfortable lounging, plush beds, well-appointed kitchen and 500+Mbps WiFi! Our bright, open living space features floor-to-ceiling windows overlooking the pool, beach and the Atlantic Ocean! The living room sectional expands into a massive lounger for all! Have a big group? We also offer the immediately next-door unit, identical to this one!

1 Minute walk to the beach *Amazing ocean view*
Enjoy Amazing ocean and beach views from your balcony. This is the 3rd unit from the ocean on the 3rd floor and honestly the view beats the direct oceanfront views because of the panoramic effect. Sea Side Villas is minutes away from the very popular Coligny Beach Park area where you can enjoy the many restaurants and shops. Also very close to the new Lowcountry Celebration Park where they have festivals and events.

Closest to Beach Path, Screened Porch, 1 dog ok
Wonderful Single Sea Pines Bungalow for 2 people. Walk 5 min on beach path. Excellent location; ride bikes to Harbor Town, Beach Club, Coligny Plaza, No elevator or parking lots! Grill out on deck. 50" TV ; screened-in porch. Walk to best beach on island, no hotels. Swimming pool onsite. Equipped Kitchen with Cooktop, Dishwasher, Refrigerator. We allow 1 dog.. under 30lbs. 4 night min bookings.
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

21 Shell Ring

47 Haul Away Estate @ Palmetto Dunes | Pool & Spa

Water Views Treehouse walkable to Harbour Town

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

Cozy beach house w/Private Heated Pool near park

Luxe Family Gem-Heated Pool~Walk to Beach~Elevator

54 Folly Field Rd - Amazing Beach Home with Pool

Island Paradise Getaway
Condo rentals with a pool

Bright & Beautiful - Steps from the Beach & Pool!

Breathtaking OCEAN VIEW/Top Floor/Pool & Coligny

1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D

Coastal Comfort! Condo in beachfront resort.

Luxury Oceanfront! KING BED 75"TV Pickleball & BAR

Stunning Ocean & Coastal Views | Resort Perks!

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Beach condo in gated resort w/ tons of amenities!
Other vacation rentals with a pool

98 Sandcastle Ct

Steps to Pool + Private Beach | Baby Gear!

#4203 Renovated/1BR/2BA/Direct Ocean Views/Sofa Bd

Starfish Beach House with Pool and Bikes

Oceanfront Villa with pool

Steps to the Beach - Perfect All-Season Getaway

Luxury Waterfront Tree House | Harbour Town | Pool

Peaceful Retreat at Seascape Villas
When is the best time to visit Hilton Head Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ540 | ﺩ.ﺇ551 | ﺩ.ﺇ650 | ﺩ.ﺇ735 | ﺩ.ﺇ735 | ﺩ.ﺇ841 | ﺩ.ﺇ863 | ﺩ.ﺇ742 | ﺩ.ﺇ646 | ﺩ.ﺇ577 | ﺩ.ﺇ551 | ﺩ.ﺇ551 |
| Avg. temp | 10°C | 12°C | 16°C | 19°C | 23°C | 27°C | 28°C | 28°C | 25°C | 20°C | 15°C | 12°C |
Quick stats about vacation rentals with a pool in Hilton Head Island

Total vacation rentals
Explore 5,700 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 138,410 verified reviews to help you choose

Family-friendly vacation rentals
4,640 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 880 rentals that welcome pets

Rentals with dedicated workspaces
3,000 properties have a dedicated workspace

Wi-Fi availability
5,560 of Hilton Head Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Hilton Head Island rentals

4.7 Average rating
Hilton Head Island stays receive an average rating of 4.7 out of 5 from guests
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- Coligny Beach Park
- Forsyth Park
- Hunting Island State Park Beach
- Harbour Town Golf Links
- North Beach, Tybee Island
- The Westin Savannah Harbor Golf Resort & Spa
- Shipyard Beach Access
- Tybee Beach Pier and Pavilion
- Bradley Beach
- Harbor Island Beach
- Mid Beach
- Secession Golf Club
- Tybee Beach point
- Dolphin Head Golf Club
- Bull Point Beach
- Congaree Golf Club
- Wormsloe Historic Site
- Driftwood Beach
- Bonaventure Cemetery
- Long Cove Club
- Seabrook Island Beach
- Hunting Island Beach
- The Beach Club
- Burkes Beach
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