
Holiday 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.

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.

(6) Location! Walk to beach and shops at Coligny
Location Location Location! Park your car and do not start it! Just renovated walk to beach / restaurants / shops / grocery across the street, if you have been to Coligny Plaza you know there are way too many places to list, but we love that the Frosty Frog and Piggly Wiggly are two of MANY places right across the street! Unit has a queen in one bedroom and two twins in the other, the sofa also pulls out to a queen as well, Roku TV, youtubetv logged in! 2 car max per unit per association.

180º Ocean Views, Treehouse "Siren's Lookout"
Waterfront and sunset views abound in this unique "treehouse", with 360 degree views. On Deer Island, just steps from the Harbour Town Lighthouse, known for its' large-boat marina, restaurants, shops and Golf Club, host of the RBC Heritage Classic, PGA Tour Event. Enjoy all the amenities of Sea Pines, including the South Beach Marina, Sea Pines Beach and Salty Dog Cafe, only 3 miles away, serviced by trollies & bike paths. Enjoy the sunset seated around the firepit. Gas grill with a view

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

Oceanfront, 3rd floor, King Bed
Direct oceanfront! Perfect for a couples get away, week vacation or anything in between. Take a walk across the street to Coligny Square where there are more than 60+ shops and restaurants. Ride your bike on more than 100 miles of trails. Onsite parking, pool and free wifi. Just bring your bathing suit and a towel! We provide the rest for you to have a relaxing vacation; beach chairs, umbrella, cooler, all kitchen spices, a Coffee Bar, shampoo, conditions, body wash and tide pods!

Oceanfront Scandi Oasis Amazing View & Heated Pool
Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 5% Home ✨ 100% New Luxury Renovation Oceanfront Balcony HGTV Featured Decorator KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR+Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT Beachfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball 2nd Pool Bike Rental Gated w/24 Hour Security Free Trolley Stop Bradley Beach

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**

5 Star Location! Pool, Walk to Shops/Dining
This luxury villa is in the heart of Hilton Head Island: Harbour Town in the world famous Sea Pines Resort- home of the PGA Heritage golf tournament! Walk to shopping, lighthouse, dining, water sports, golf, tennis, entertainment, and boat charters! The complimentary, seasonal beach shuttle picks up at the villa and drops off at the Sea Pines Beach Club. Impeccably appointed and sparkling clean with lagoon views. The complex has a private pool and clay tennis courts.

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.
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

Governor’s Quarters: Stately Sea Pines Stay on HHI

Sea Pines Home! Walk to Beach | Lagoon View & Pool

47 Haul Away Estate @ Palmetto Dunes | Pool & Spa

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

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

Encanto of the Lowcountry in Old Town Bluffton

Peaceful Harbour Town Treehouse with Marsh Views

Luxe Family Gem-FREE Heated Pool~Walk to Beach~BBQ
Apartment rentals with a pool

Beach condo with pool and stunning nature views

Breathtaking OCEAN VIEW/Top Floor/Pool & Coligny

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Walk to Beach 2BR Condo with Pool & Tennis

3BD/2BA condo - Private beach access & 3 pools!

1BR/2BA condo w/private beach access in Shipyard

Beach Front Villa Oak Tree Lined Views to Water

Oceanfront Breathtaking Views
Other holiday rentals with a pool

21 Shell Ring

Blue Heron at Seaside

5 Bedroom-Beach Access-Pool-Sleeps 14!

Harbourside Haven

Oceanfront Villa with pool

Jim's Direct Oceanfront 3BR Penthouse Villa

XMas in Sea Pines! 2 Bdrm W/Bikes, Pets Welcome!

Beach & Birdie Kid Friendly Close to Beach & Golf
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 | $192 SGD | $196 SGD | $231 SGD | $261 SGD | $261 SGD | $299 SGD | $307 SGD | $264 SGD | $230 SGD | $205 SGD | $196 SGD | $196 SGD |
| 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 holiday rentals with a pool in Hilton Head Island

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

Nightly prices starting at
Hilton Head Island holiday rentals start at $13 SGD per night before taxes and fees

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

Family-friendly holiday rentals
4,640 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 880 rentals that welcome pets

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

Wifi availability
5,560 of Hilton Head Island holiday rentals include wifi 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
- North Beach, Tybee Island
- Harbour Town Golf Links
- 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
- Wormsloe Historic Site
- Congaree Golf Club
- Long Cove Club
- Bonaventure Cemetery
- Seabrook Island Beach
- The Beach Club
- Hunting Island Beach
- St. Catherines Beach
- Islanders Beach Park
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