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

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

Nightly prices starting at
Hilton Head Island holiday rentals start at $68 NZD per night before taxes and fees

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

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

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

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

Wi-Fi availability
6,120 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

4.8 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.

Lovely 3BR in Palmetto Dunes w/ new pool & spa
Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. Two King BRs, 3rd BR with 2 Queens. Flat screen TVs, cable, ROKU in all BRs. Doorbell cam at front door porch with recording capability for host/guest safety. Beach access @ Omni resort and Dunes House is 5-10 min by bike or 15 min walk. Beach towels/umbrella/chairs not provided. Pool/spa heat unavailable after 6/1/26
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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.
ValueFamilyLayout

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!
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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.
LocationFamilyLaundry

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.
ValueLocationOutdoor spaces

Harbour Town Marina Studio | Walk to Lighthouse
Cozy, bright penthouse studio with direct views of the Harbour Town Marina, just steps from the lighthouse, shops, dining, and golf. The space features a comfortable sleeping area with king bed, sitting space, kitchenette, and full bath with tub/shower combo. Enjoy the small private balcony, perfect for morning coffee or evening sunsets over the marina. Ideal for 1–2 guests looking to enjoy the Harbour Town lifestyle in Sea Pines. Located on the fourth floor with convenient elevator access.
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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!
LocationValueSleep quality

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**
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Anchor at the Beach ⛱ Eat & Shop at Coligny plaza!
Oceanfront building with a side view of the ocean from the balcony. Park your car and walk to everything. This beautiful 2 bed/2 bath beach condo is perfect for your family vacation or romantic getaway. No streets to cross to get to the beach! Location, location, location. Gated entry, private, and just a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants). I also provide beach chairs, umbrella, and beach cart for your convenience during your stay! #072058
ValueFamilySleep quality

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.
ValueLocationLayout

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.
LocationFamilySleep quality

Walk to Ocean | Pool | Large Bedrooms | Sea’Esta
Please see our almost 1000 5-star reviews at our other properties. This spacious completely remodeled, top floor villa is within a 5-10 minute walk to the beach and everything else, including a seasonal pool, several restaurants, general store, wine bar, tennis, golf, kayaks/canoes, bikes, fishing and so much more. Each master/en-suite has two Queen beds and every amenity you could imagine. Bathrooms are spacious with closed off toilet/showers.
LocationFamilyAccuracy
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

Stately Governors Quarters-Pet Friendly, Fenced In
LocationFamilyCleanliness

6 BR, Sleeps 26, Beach Time
FamilyLocationNearby

Starfish Beach House with Pool and Bikes
FamilyLocationWalkability

Upscale Retreat w Pool & Spa | Palmetto Dunes
LocationFamilyBeach

Palmetto Dunes House: Private Pool, PDBeach, Golf
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Updated! Sea Pines Lagoon View Oasis
FamilyLocationComfort

Coastal Fairways
LocationFamilyKitchen

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

South end newly renovated first floor 2 bd condo
LocationValueLaundry

My Blue Heaven, Direct Ocean Front View
ValueFamilyLong stay

1BR/2BA condo w/private beach access in Shipyard
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Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
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Few mins walk to beach 1st flr pools hot tub pball
LocationFamilyGetting around

Ocean View with Beach Access
ValueLocationAmenities

Sunny Treetop Getaway w/ tennis and pickleball
FamilyLocationComfort

Newly Renovated Condo!
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Other holiday rentals with a pool

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

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
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Peaceful Retreat at Seascape Villas
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Near Beach Condo w/ Pool · Hot Tub · Pickleball
LocationFamilyCondition

Private Pool | Golf | Exq. Coffee | Seascape
LocationValueQuiet

Ocean Views at Villamare 1405, Steps to the Beach!
ValueFamilyHot tub

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

Pet friendly condo with amazing Broad Creek views
LocationFamilySleep quality
When is the best time to visit Hilton Head Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $279 NZD | $280 NZD | $331 NZD | $365 NZD | $364 NZD | $426 NZD | $399 NZD | $343 NZD | $299 NZD | $287 NZD | $287 NZD | $280 NZD |
| 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
- Edisto Beach State Park
- Bonaventure Cemetery
- Hunting Island State Park
- Shelter Cove Towne Centre
- Oatland Island Wildlife Center
- Kiawah Beachwalker Park
- Skidaway Island State Park
- Wormsloe Historic Site
- Cathedral of Saint John the Baptist
- Fort Pulaski National Monument
- Savannah College of Art and Design
- Owens-Thomas House
- Seabrook Island Beach
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Sheldon Church Ruins
- Coastal Discovery Museum
- Things to do Hilton Head Island
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