
Vacation rentals with a pool in Hilton Head Island
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Hilton Head Island

Total vacation rentals
Explore 6,120 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at $56 CAD per night before taxes and fees

Verified guest reviews
Over 138,130 verified reviews to help you choose

Family-friendly vacation rentals
5,010 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 1,000 rentals that welcome pets

Rentals with dedicated workspaces
3,280 properties have a dedicated workspace

Wifi availability
6,120 of Hilton Head Island vacation rentals include wifi 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!
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.

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!

Ocean Gate 13 Walk to beach villa with pickleball
This villa is perfect for the family beach vacation! We have little ones ourselves, so we've got all the gear needed to make this a comfortable and relaxing stay. We LOVE this villa because of its screened in porch, FREE TENNIS, and proximity to the beach. The screened in porch allows you to enjoy breakfast and happy hour free from mosquitoes and close enough to hear the waves! The beaches are far less crowded than other areas of the island, and it's very close to Sea Pines and Coligny Plaza.

The Lookout - A Modern Beach Retreat (Oceanfront)
Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

Fully Renovated 2 Bedroom Villa - Walk to Beach
Make yourself at home in this comfortable 2 story, ground floor Condo. Easy walk to the beach. Open concept living, dining and fully equipped kitchen and 1/2 bath on main floor. Chose either the comfy King or Queen bedroom with walk-in shower or bathtub of your choice. Private courtyard with Grill and outside seating. All this, in a setting of azaleas, palms and 20 steps to pool with stores and restaurants just 2 blocks away. Please note there is only 1 parking space available for your stay.

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

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.

Beachfront Resort 2B Golf Beach Pickleball Tennis
✨Top 5% Guest Favorite✨ Gated Beachfront Resort Golf, Tennis, Pickleball, Pool, Restaurants & Bars Gorgeous Sunny Villa Panoramic Lagoon & Golf Views! Beautiful & Lush Scenery Huge Old Oaks dripping in Spanish Moss! Walk/Bike to Beach Abundant Wildlife! Walk to Shipyard Golf Club & Pub! Modern Coastal Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen Walk-in Shower Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

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**

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.

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.

HHI South Forest beach/WLK TO BEACH, dining, pool
Pack up the whole crew—two-legged or four—and escape to this fully furnished, perfectly located cozy condo in Hilton Head’s popular Treetops complex. Enjoy three refreshing pools, tennis courts, and a laid-back vibe perfect for relaxing or playing. Just a 10-minute walk to the beach and steps from Coligny Plaza, you’ll be close to shopping, dining, and all the island fun. It’s your ideal home base for sun, sand, and good times!
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

6 BR, Sleeps 26, Beach Time

Stately Governors Quarters-Pet Friendly, Fenced In

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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

Upscale Retreat w Pool & Spa | Palmetto Dunes

Palmetto Dunes House: Private Pool, PDBeach, Golf

Coastal Fairways

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

South end newly renovated first floor 2 bd condo

My Blue Heaven, Direct Ocean Front View

Few mins walk to beach 1st flr pools hot tub pball

Beach Front Villa Oak Tree Lined Views to Water

Stunning Ocean & Coastal Views | Resort Perks!

Ocean View with Beach Access

Sunny Treetop Getaway w/ tennis and pickleball

Secluded 1st Floor ~ 2 Bed/2 Bath Beach Getaway
Other vacation rentals with a pool

Harbour Town Marina Studio | Walk to Lighthouse

Wren's Nest - 4BR SeaPines Retreat+Backyard Oasis

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

Peaceful Retreat at Seascape Villas

Incredible Hilton Head condo - private beach!

Renovated 1BR HHI – Walk to Beach & Salty Dog Café

Ocean Views at Villamare 1405, Steps to the Beach!

Luxury Palmetto Dunes Retreat with Private Pool
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 | $228 CAD | $230 CAD | $271 CAD | $299 CAD | $298 CAD | $349 CAD | $327 CAD | $281 CAD | $245 CAD | $235 CAD | $235 CAD | $230 CAD |
| 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 |
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- Rentals with pools Beaufort County
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- Savannah Historic District
- Coligny Beach Park
- Forsyth Park
- Hunting Island State Park Beach
- Harbour Town Golf Links
- North Beach, Tybee Island
- Tybee Beach Pier and Pavilion
- Harbour Town Lighthouse
- Edisto Beach State Park
- Bonaventure Cemetery
- Hunting Island State Park
- Shelter Cove Towne Centre
- Kiawah Beachwalker Park
- Oatland Island Wildlife Center
- Skidaway Island State Park
- Jepson Center for the Arts
- Wormsloe Historic Site
- Cathedral of Saint John the Baptist
- Savannah College of Art and Design
- Fort Pulaski National Monument
- Owens-Thomas House
- Seabrook Island Beach
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Things to do Hilton Head Island
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