
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.

A "WOW" factor-Palmetto Dunes Retreat in Turnberry
Come to enjoy a relaxing time in Palmetto Dunes Resort at Turnberry Village- located in the heart of Hilton Head overlooking the 9th & 10th hole of the Robert Trent golf course. This villa has it all- newly updated villa, deck with golf course view, secluded location, and fully equipped with modern decor, appliances, and linens to make your stay a memorable and enjoyable vacation. There are 3 miles of sun-kissed beaches, world-class golf, restaurants, shopping and 11 miles of lagoons to enjoy.

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.

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR
✨Top 1% Airbnb Home✨ PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony - Watch Sunrise / Hear Waves! Beachfront Pool, Bar & Grille FREE Pickleball, Tennis, Gym, Volleyball & More HGTV Designer Renovation KING BED + Two 65" SmartTVs Spa Bath Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

Oceanfront Luxury! KING BED Pickleball + Beach Bar
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨See the Ocean Sunrise & Hear the Waves! ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball, Basketball, Volleyball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT No Resort Fees! Beachfront Pool w/Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

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.

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.

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.

5 Star Location-Pool, Walk to Dining/Shops/Marina
Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

"After Dune Delight"-Admirals Row 220- HHBT 2B/2B
Our villa is a stunning 2 bedroom unit that is just steps from the beach. It is your home away from home! A full size balcony with plenty of room to entertain your family, friends, or just relax and enjoy the ocean view. Beach chairs are provided for your use, so no need to clutter up your car bringing them! Beautiful fully equipped kitchen with dining area with seating for 6. Enjoy the ocean breezes while watching the sunrise.

TOP Floor Oceanfront | Remodeled | Coligny Beach
Wake up to breathtaking, unobstructed views of the Atlantic Ocean in this newly remodeled, direct oceanfront one-bedroom condo in the heart of Coligny Beach. Designed in a relaxed coastal-chic style, this intimate retreat is perfect for couples or guests traveling with an infant. Walk to the beach, dining, shopping, and live music—or fly into HHI and enjoy a completely car-free stay.
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

98 Sandcastle Ct

6 BR, Sleeps 26, Beach Time

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Steps to the Beach - Perfect All-Season Getaway

Private pool/spa : pool heat available : Kg master

Modern Beach Escape | Private Pool~Steps to Beach

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King beds*grill*gms
Condo rentals with a pool

A+ Condo! 2 Min to Beach~ Ocean View~2 Bikes! #109

Beach Front Villa Oak Tree Lined Views to Water

1 Bedroom Condo, 5 Minute Walk to the Beach

Beachfront + Walk Everywhere | Pool

Steps to Beach Coastal King | Walk to Everything!

Oceanfront Breathtaking Views

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

Heron's Haven on Port Royal Sound, 2BR/2BA
Other vacation rentals with a pool

First Floor - 50 Yards to Sand- Partial Oceanview

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

Harbourside Haven

Luxury Oceanview King Villa|Sunrises-Steps to Sand

Jim's Stunning Direct Ocean Front 2BR Villa

Gated beachfront villa w/ Pool+Bikes

Peaceful Retreat at Seascape Villas

Oceanfront Condo w/ Balcony | Sea Side Villas HHI
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.ﺇ621 | ﺩ.ﺇ621 | ﺩ.ﺇ606 |
| 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 5,760 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

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

Family-friendly vacation rentals
4,740 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
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 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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- Rentals with pools Beaufort County
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- Coligny Beach Park
- Savannah Historic District
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- River Street
- Tybee Beach Pier and Pavilion
- Bonaventure Cemetery
- Wormsloe Historic Site
- Enmarket Arena
- Fort Pulaski National Monument
- Skidaway Island State Park
- Old Fort Jackson
- Cathedral of Saint John the Baptist
- Edisto Beach State Park
- Savannah College of Art and Design
- Chippewa Square
- Coastal Discovery Museum
- Hunting Island State Park
- Oatland Island Wildlife Center
- Kiawah Beachwalker Park
- Tybee Island Light Station
- Tybee Island Marine Science Center
- Harbour Town Lighthouse
- Things to do Hilton Head Island
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