
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.

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway
Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

Oceanfront Villa on Hilton Head Island!
This one bedroom, one bath oceanfront Villa is a third floor end unit that sleeps 5. There’s an adjustable queen bed, a set of bunk beds (Intended for children) and a twin sleeper sofa. It is a three minute walk to the sandy shores of Hilton Head Island. The gated resort has these amenities: two pools (one of which is the largest beach front pool on the island), 10 tennis courts, pickle ball courts, fitness center, bike rental, playground, and three restaurants. Reserve your vacation today! Thi

1BR/2BA condo w/private beach access in Shipyard
This large, tastefully decorated 1BR / 2BA condo, located in Shipyard, has everything you need to kick back with family or friends. Enjoy a morning coffee or evening cocktail on the large wrap around deck. Spacious and comfortable master bedroom with king bed, walk-in closet, en-suite bath, and seating area. Fully equipped kitchen with an adjacent seating area for six. Queen sleeper sofa in the living room and second full bath with shower. In unit washer/dryer. Clean fee includes 1 car pass.

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!

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.

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.

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.

Jim's Stunning Direct Ocean Front 2BR Villa
This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

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

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 1% Home ✨ Oceanfront Balcony 100% New Luxury Renovation HGTV Featured Decorator KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/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

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**
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

Beach Bungalow in Sea Pines’ Night Heron Community

98 Sandcastle Ct

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

Sea Pines Home! Walk to Beach | Lagoon View | Pool

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Modern Beach Escape | Private Pool~Steps to Beach

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

Island Getaway - an iTrip Hilton Head Home
Condo rentals with a pool

Oceanview King Villa | Elevated Couples Escape

Sea la Vie @Fiddler's Cove

1st Floor-Beach Access-2 Pools-Hot tub-Pickleball

Sea Pines Condo, 2 Bdrm/2Ba w/Bikes! Pets welcome!

Southern Serenity, an HHI Beachfront Resort

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

Hilton Head 2br/2ba Condo -Newly Updated

Luxury KING BED 65"TV Bar FREE Pickleball & Gym
Other vacation rentals with a pool

Courtside! Walk to beach, park, tennis and Coligny

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

Oceanfront Villa with pool

Relaxing Beachfront Villa

Pet friendly condo with amazing Broad Creek views

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

Modern condo 2 BR 2 bath w/sleeper-sofa

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$30,746 GYD | G$31,374 GYD | G$37,021 GYD | G$41,832 GYD | G$41,832 GYD | G$47,897 GYD | G$49,152 GYD | G$42,250 GYD | G$36,812 GYD | G$35,348 GYD | G$35,348 GYD | G$34,511 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 5,760 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at G$4,183 GYD 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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- Coligny Beach Park
- Savannah Historic District
- River Street
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- Tybee Beach Pier and Pavilion
- Bonaventure Cemetery
- Wormsloe Historic Site
- Enmarket Arena
- Skidaway Island State Park
- Savannah College of Art and Design
- Cathedral of Saint John the Baptist
- Old Fort Jackson
- Oatland Island Wildlife Center
- Coastal Discovery Museum
- Kiawah Beachwalker Park
- Chippewa Square
- Fort Pulaski National Monument
- Edisto Beach State Park
- Daffin Park
- Pirates Of Hilton Head
- Tybee Island Light Station
- Hunting Island State Park
- Things to do Hilton Head Island
- Art and culture Hilton Head Island
- Food and drink Hilton Head Island
- Tours Hilton Head Island
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- Nature and outdoors Hilton Head Island
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- Nature and outdoors Beaufort County
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