
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.

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR
☀️Time to BOOK YOUR HILTON HEAD ESCAPE. Wake up to sweeping oceanfront views from this top-floor Breakers villa, where sunrise steals the show. Watch dolphins & sip morning coffee on your private balcony, then walk just steps to the beach, pool, restaurants, and shopping at Coligny Plaza—no car required. Perfect for a romantic getaway or small family vacation, with exclusive deals on bikes & dolphin tours. This bright condo offers unbeatable location, privacy, and a stress-free island stay. 🐬🚲

Wide Ocean View 65"TV Pickleball BAR GYM Tennis
✨ Top 5% Airbnb Guest Favorite ✨ Wide Ocean View from Living Room & Balcony! SNOWBIRDS: Warm, Sunny South Facing Balcony Oceanfront Building Steps to Beach & Pool Updated by HGTV Decorator FREE: Pickleball, Tennis, Gym, Volleyball + More Top Floor Hear the Wave 2 XL SmartTVs Beach Chairs, Ice Chest & More Couples Retreat / Small Families RESORT: Elevator Oceanfront Pool w/Tiki Bar & Grille Sports Bar 3 Restaurants Bike Rentals on Site 2nd Pool Playground Gated 24/7 Security 4 Beach Boardwalks

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway
Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

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! Thi

Luxury OceanView KING BED 75"TV Gym BAR Pickleball
✨Top 5% Airbnb Home✨ BIG OCEAN VIEWS FROM LIVING ROOM & BALCONY! Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar! FREE Pickleball, Tennis, Gym & More HGTV Featured Decorator 100% NEW Luxury renovation KING BED + 75" & 65" Smart TVs Expanded Bedroom Luxe Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

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.

1BR/2BA condo w/private beach access in Shipyard
This large, tastefully decorated 1BR / 2BA condo, located in Shipyard, has everything you need to kick back with family or friends. Enjoy a morning coffee or evening cocktail on the large wrap around deck. Spacious and comfortable master bedroom with king bed, walk-in closet, en-suite bath, and seating area. Fully equipped kitchen with an adjacent seating area for six. Queen sleeper sofa in the living room and second full bath with shower. In unit washer/dryer. Clean fee includes 1 car pass.

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!

Stylish Tennis-Golf- Beach Retreat-Renovated!
Welcome to my home! The condo is located in a lush gated community with tennis, golf, and beach, south end of the island, close to all the tourist attractions. Things you can do without getting in your car: stroll on the beach, have a meal at the Sonesta resort, suntan at the community pool, play golf or tennis, ride bicycles. Pet's MUST be included in reservation dropdown at booking. Approval for 2nd dog prior to booking with additional fee charged. Pets are not allowed on the furniture.

My Blue Heaven, Direct Ocean Front View
Welcome to our ocean front rental, a haven for couples seeking a romantic and stylish getaway. With its breathtaking ocean view, five-star reviews, and recent remodel in 2023, this rental promises an unforgettable experience. Our guests have praised the attention to detail, the stunning view, and the overall ambiance of the space. Rest assured that your stay will be nothing short of extraordinary. Step out onto the balcony and take in the fresh sea breeze as you relax in the swinging chair.

Jim's Stunning Direct Ocean Front 2BR Villa
This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

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

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Resort-Style Pool, Cute House 88 Steps to Sand

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

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

Island Getaway - an iTrip Hilton Head Home

Encanto of the Lowcountry in Old Town Bluffton

Peaceful Harbour Town Treehouse with Marsh Views
Condo rentals with a pool

Quick Walk to Beach- 2BR/1BA - South Forest Beach

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Oceanside Beach Retreat

Family/Couples Condo Retreat - Walk to Beach/Shops

Oceanfront Breathtaking Views

King Size & Sunrises

Stunning Oceanview Luxury Remodel, Bikes Included!

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐
Other holiday rentals with a pool

Sea la Vie @ Fiddler's Cove

Oceanfront Villa with pool

The Breakers- Direct Oceanfront-Pool

Modern Beach Escape | Private Pool~Steps to Beach

Direct oceanfront, first floor, 65" TV, elite golf

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

Direct Ocean Front S. Forest Beach

Seas the Day! 2BR/2BA/Walk to Beach/Dogs welcome!
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 | $207 AUD | $211 AUD | $249 AUD | $281 AUD | $281 AUD | $322 AUD | $330 AUD | $284 AUD | $247 AUD | $238 AUD | $238 AUD | $232 AUD |
| 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 5,760 holiday rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 136,170 verified reviews to help you choose

Family-friendly holiday rentals
4,740 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 910 rentals that welcome pets

Rentals with dedicated workspaces
3,350 properties have a dedicated workspace

Wi-Fi availability
5,730 of Hilton Head Island holiday 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
- Savannah Historic District
- River Street
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- Tybee Beach Pier and Pavilion
- Bonaventure Cemetery
- Wormsloe Historic Site
- Enmarket Arena
- Skidaway Island State Park
- Savannah College of Art and Design
- Cathedral of Saint John the Baptist
- Old Fort Jackson
- Oatland Island Wildlife Center
- Coastal Discovery Museum
- Kiawah Beachwalker Park
- Chippewa Square
- Fort Pulaski National Monument
- Edisto Beach State Park
- Daffin Park
- Pirates Of Hilton Head
- Tybee Island Light Station
- Hunting Island State Park
- Things to do Hilton Head Island
- Art and culture Hilton Head Island
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- Nature and outdoors Hilton Head Island
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- Things to do South Carolina
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