
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.

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

Prime Spot: Harbour, Dining, Shops & Beach
Stay in the heart of it all at this upscale, centrally located guest suite (256 sq ft) with independent entrance, total privacy, queen bed and full bath (no kitchen). Step outside to waterfront restaurants, live music, bars, shops, and summer weekly fireworks. Supermarkets and more dining are just a 10-minute walk away. Enjoy a free shuttle to attractions within 2-mile radius (April–September). Golfing, biking, fishing, and water sports all nearby, free access to Palmetto Dunes Beach community.

Ocean View! Remodeled! Steps to beach/Pool/Bar
FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!

Coastal King Beach Flat Convenient to Everything!
Set in a serene location right on the beach, this complex is a peaceful gated retreat. It's a short walk to Coligny Plaza, a vibrant area offering a variety of dining, shopping, and entertainment options. The complex features a pool and sundeck, perfect for relaxation. With high-speed internet, WIFI, smart TVs, Roku, and cable, you're always connected. Enjoy the comforts of home with a fully stocked kitchen, a plush King bed, ideal for remote work, and modern updates & included amenities.

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 .

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.

Hilton Head Villa With Golf View, Stroll to beach
Proudly selected by HGTV as one of nine “Wow Worthy Vacation Homes and Design on HHI”, alongside the 2020 HGTV Dream Home. This upscale home offers seamless in/outdoor living and a generous granite kitchen. During your stay, enjoy the comforts of home - from the plush sectional sofa and Smart TV's, to the hotel-like King bed and en suite bathroom in the master suite. Enjoy the indoor/ outdoor living of your own private villa in the exclusive Greens community of Shipyard Plantation.

Luxury Oceanfront! KING BED 75"TV Pickleball & BAR
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 1% 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**

Ocean Front Resort Condo
Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

47 Haul Away Estate @ Palmetto Dunes | Pool & Spa

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Hilton Lagoon by AvantStay | Designer Home + Pool

Water Views Treehouse walkable to Harbour Town

Private pool/spa : pool heat available : Kg master

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

Marsh Views | Pool, HotTub, Game Room&Pet Friendly

Great spot for families, golf cart included
Condo rentals with a pool

Turtle Tracks, Hilton Head Island, SC

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Gorgeous Ocean View 65"TV Pickleball BAR GYM

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

My Blue Heaven, Direct Ocean Front View

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

1st Floor-Beach Access-2 Pools-Hot tub-Pickleball

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa
Other holiday rentals with a pool

Luxury Oceanfront! KING BED 75"TV Pickleball & BAR

Steps to the Beach - Perfect All-Season Getaway

Gated beachfront villa w/ Pool+Bikes

Luxury Waterfront Tree House | Harbour Town | Pool

Sea Pines Condo, 2 Bdrm/2Ba w/Bikes! Pets welcome!

Beach condo in gated resort w/ tons of amenities!

Beach & Birdie Kid Friendly Close to Beach & Golf

Marriott Harbour Point - 2BD
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 | $255 NZD | $260 NZD | $307 NZD | $347 NZD | $347 NZD | $397 NZD | $407 NZD | $350 NZD | $305 NZD | $272 NZD | $260 NZD | $260 NZD |
| 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 $17 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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 holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Things to do Hilton Head Island
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