
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 OceanView KING BED 75"TV Gym BAR Pickleball
✨Top 10% 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

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.

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony - Watch Sunrise / Hear Waves! Beachfront Pool, Tiki 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

1st Floor, 1 BR Condo - Steps to Beach and Pool!
Renovated 1st floor, 1 BR getaway located across the street from the beach! Private deck overlooks community pool just steps from back door. Great location - plenty of restaurants, bars, shopping and grocery stores nearby. New appliances, smart TVs in living area and bedroom (cable in living room). Bedroom has a queen-size bed and brand new leather recliner sofa in the living room. Rental includes 2 beach chairs, cart and umbrella. Absolutely no pets and no smoking allowed.

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-Harbourtown-Walkable Area
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.

Private pool/spa : pool heat available : Kg master
Private pool and 4 person spa! Enjoy breakfast by the pool with the birds chirping and end your day relaxing in the spa under the stars! ‣1800 ft² , One level ‣Parking for 4 cars ‣Fully equipped kitchen ‣Washer/Dryer ‣2 Living/Seating areas ‣Dining table for 8/Island seats 4 ‣Bunk room with 2 triple bunkbeds ‣King master w/ desk space ‣Smart TVs ‣Pool Heating available for extra fee ➼Folly Field Beach: 0.5 mi/5 min bike/12 min walk

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

6 BR, Sleeps 26, Beach Time

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Private Pool + Golf Views | Relaxing HHI Retreat

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Steps to the Beach - Perfect All-Season Getaway

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

Cozy beach house w/Private Heated Pool near park

Private Pool/Spa | Golf | Exq. Coffee | Seascape
Condo rentals with a pool

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Ocean front condo with amazing ocean view!

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway

South end newly renovated first floor 2 bd condo

Ocean Views at Villamare, Right on the Beach!

Ocean View! Remodeled! Steps to beach/Pool/Bar

Private comfy condo, steps away from the beach

Steps to Beach Coastal King | Walk to Everything!
Other vacation rentals with a pool

Harbourside Haven

Private Oasis w/ Pool ~ Pet Friendly ~ Fenced Yard

Brand New Lux Condo - Ocean View! Steps to Beach!

Marriott Barony Beach 2BR/2Bath Sleeps 8

Seas the Day! 2BR/2BA/Walk to Beach/Dogs welcome!

Beach Front Condo!

Steps to the Surf! Top-Floor w/Stunning Ocean View

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 | G$30,701 GYD | G$31,328 GYD | G$36,966 GYD | G$41,770 GYD | G$41,770 GYD | G$47,827 GYD | G$49,080 GYD | G$42,188 GYD | G$36,758 GYD | G$35,296 GYD | G$35,296 GYD | G$34,460 GYD |
| 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 5,250 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at G$8,354 GYD per night before taxes and fees

Verified guest reviews
Over 128,680 verified reviews to help you choose

Family-friendly vacation rentals
4,310 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 900 rentals that welcome pets

Rentals with dedicated workspaces
2,770 properties have a dedicated workspace

Wi-Fi availability
5,240 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

4.8 Average rating
Hilton Head Island stays are highly rated by guests—averaging 4.8 out of 5!
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- Coligny Beach Park
- Savannah Historic District
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- Tybee Beach Pier and Pavilion
- Bonaventure Cemetery
- Wormsloe Historic Site
- Enmarket Arena
- Edisto Beach State Park
- Skidaway Island State Park
- Fort Pulaski National Monument
- Cathedral of Saint John the Baptist
- Savannah College of Art and Design
- Old Fort Jackson
- Chippewa Square
- Oatland Island Wildlife Center
- Hunting Island State Park
- Coastal Discovery Museum
- Harbour Town Lighthouse
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Kiawah Beachwalker Park
- Henry C Chambers Waterfront Park
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