
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.

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6
Enjoy 4th Floor Ocean Views. Remodeled w/Upscale Finishes & Furniture. King Master Bdrm, 2 Dressers, Nightstands, TV, AC unit. Bath w/Body Spray Rain Shower, Comfort Hgt Toilet, Vanity w/Granite Counter/Storage. Hall BunkBeds w/Over Sized Drawers, USB Storage Alcoves, Oscillating Fan. Kitchen Pullout Drawer Cabinets, SS Apps, Double Oven, Granite Counters. Dining w/Table for 3/4 & 2 at Kitchen Bar. LR Queen SleeperSofa, Flat Screen TV, DVR, Chair, Ottoman, AC unit. Balcony Comfy Seating for 4.

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

Beach Resort 2b Luxury Golf Lagoon View Pickleball
Gated Beach & Golf Resort! ✨ Top 10% Airbnb Guest Favorite ✨ Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis – across the street HGTV Decorator designed Panoramic Golf & Lagoon Views! Big Porch Huge Old Oak trees! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FREE: FAST WIFI & CABLE Marble Kitchen Washer/Dryer Beach Cart, Chairs, Boogie Boards, Ice Chest BBQ Walk & Bike Path to Beach! Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D
Welcome to "Tygers on the Beach" at Fiddler's Cove. This 1st floor fully equipped villa is 300 yards to the private beach access. The pristine beach is one of the least crowded on the island, making it ideal for families. Lounge in the heated pools, relax in the hot tub or play tennis/pickleball on site. Enjoy golf course views from the patio, king-size master bed and easy access to the bike trails, restaurants, and shops that make Hilton Head Island the perfect place to relax & unwind.

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.

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

Ocean Overlook - The Ultimate Vacation Experience
LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

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 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.

Ocean Views at Villamare, Steps to the Beach!
Read our reviews! We strive to provide an unforgettable Hilton Head experience in our renovated villa with ocean views, comfortable lounging, plush beds, well-appointed kitchen and 500+Mbps WiFi! Our bright, open living space features floor-to-ceiling windows overlooking the pool, beach and the Atlantic Ocean! The living room sectional expands into a massive lounger for all! Have a big group? We also offer the immediately next-door unit, identical to this one!
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

98 Sandcastle Ct

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

47 Haul Away Estate @ Palmetto Dunes | Pool & Spa

Water Views Treehouse walkable to Harbour Town

Modern Beach Escape | Private Pool~Steps to Beach

Luxe Family Gem-Heated Pool~Walk to Beach~Elevator

54 Folly Field Rd - Amazing Beach Home with Pool

109 Dune Lane - Oceanfront Paradise
Condo rentals with a pool

Bright & Beautiful - Steps from the Beach & Pool!

Ocean & Marsh View KING BED 65"TV Bar Pickleball!

(4) Location! Walk to Coligny Beach Shops Dining!

2 Min to Beach! King bed! Ocean View! 2 Bikes~218

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Exclusive Oceanfront Decorator Decor Spacious Bdrm

Sunny Treetop Getaway w/ tennis and pickleball

Pool + Beach Views | Sauna | Indoor Pool
Other vacation rentals with a pool

Beach Bungalow in Sea Pines’ Night Heron Community

Steps to Pool + Private Beach | Baby Gear!

Starfish Beach House with Pool and Bikes

Beachfront Sand & Sea Retreat

Beach Resort: Indoor & Outdoor Pools + Boardwalk

Gated beachfront villa w/ Pool+Bikes

Luxury Waterfront Tree House | Harbour Town | Pool

Peaceful Retreat at Seascape Villas
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$30,743 GYD | G$31,370 GYD | G$37,017 GYD | G$41,827 GYD | G$41,827 GYD | G$47,891 GYD | G$49,146 GYD | G$42,245 GYD | G$36,807 GYD | G$32,834 GYD | G$31,370 GYD | G$31,370 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 5,700 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at G$2,091 GYD per night before taxes and fees

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

Family-friendly vacation rentals
4,640 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
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 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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- 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
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