
Holiday rentals with a pool in Hilton Head
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hilton Head
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Wide Ocean View 65"TV Pickleball BAR GYM Tennis
✨ Top 5% Airbnb Guest Favorite ✨ Wide Ocean View from Living Room & Balcony! SNOWBIRDS: Warm, Sunny South Facing Balcony Oceanfront Building Steps to Beach & Pool Updated by HGTV Decorator FREE: Pickleball, Tennis, Gym, Volleyball + More Top Floor Hear the Wave 2 XL SmartTVs Beach Chairs, Ice Chest & More Couples Retreat / Small Families RESORT: Elevator Oceanfront Pool w/Tiki Bar & Grille Sports Bar 3 Restaurants Bike Rentals on Site 2nd Pool Playground Gated 24/7 Security 4 Beach Boardwalks

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

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!

98 Sandcastle Ct
98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

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.

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

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**

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa
Welcome to our renovated 2BR 2BA Villa at Hilton Head Beach & Tennis Resort. It is a short walk to the Resort's beautiful Private Access Beach and largest outdoor pool on the Island Updated appliances, furniture & bathrooms. Villa has a fully equipped Kitchen, Coffee Bar with Keurig, Memory Foam Mattresses on all Beds 3 Wall Mounted Smart TV's Hi Speed Wifi. Sleeps 5 adults Comfortably contact us for info on add'l guests. Porta Crib supplied but guest must bring own linens for crib

Hilton Head 2br/2ba Condo -Newly Updated
Located in Hilton Head Beach & Tennis Resort on the first floor. Extremely short walk to the beach. The gated resort features 2 pools, 3 restaurant's, tennis courts, & a playground. Condo is newly updated featuring an open layout to include dining room, fully equipped kitchen and two bedrooms (Queen bed,2 twin beds, and one rolling folding bed with mattress). All TVs are smart TVs & feature cable. - Largest oceanfront pool on island - Beach Bar - Restaurant & Sports Bar - Pickleball

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.

Lovely family Villa Close to Beach
Welcome to Fiddlers Cove. We offer you a great vacation experience in a 2 bedroom, 2 bathroom apartment, 5 minute walk to Folly Field Beach. The apartment has everything you need. Fully equipped kitchen, toys, puzzles, highchair, booster, beach toys, and of course the ocean. **No need to buy bottles of water. We have a water purifier built into the kitchen sink. Bring your refillable water bottles and save. Enjoy the fresh ocean air and the sunset from the balcony.
Popular amenities for Hilton Head rentals with a pool
House rentals with a pool

6 BR, Sleeps 26, Beach Time

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

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Resort-Style Pool, Cute House 88 Steps to Sand

NEW! Excellent Remodeled Best Beach & Tennis Villa

Private pool/spa : pool heat available : Kg master

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

Encanto of the Lowcountry in Old Town Bluffton
Condo rentals with a pool

Modern villa for vacation or remote work getaway!

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR

Ocean View 1-bdrm. Steps to the Beach and Pool.

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

Beach Front Resort - Ocean View King Bed

Coastal Beach Getaway for Sunsets & Flip Flops HHI

1 Bedroom Condo, 5 Minute Walk to the Beach

Pool side condo just steps from beach boardwalk!
Other holiday rentals with a pool

First Floor - 50 Yards to Sand- Partial Oceanview

#4203 Renovated/1BR/2BA/Direct Ocean Views/Sofa Bd

Oceanfront Villa with pool

Sea la Vie @ Fiddler's Cove

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

Marriott Sunset Pointe - 2BD

Direct oceanfront, first floor, 65" TV, elite golf

King Size & Sunrises
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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
- Angel Oak Tree
- Bonaventure Cemetery
- Wormsloe Historic Site
- Enmarket Arena
- Skidaway Island State Park
- Savannah College of Art and Design
- Oatland Island Wildlife Center
- Old Fort Jackson
- Cathedral of Saint John the Baptist
- Coastal Discovery Museum
- Edisto Beach State Park
- Pirates Of Hilton Head
- Tybee Island Light Station
- Fort Pulaski National Monument
- Kiawah Beachwalker Park
- Tybee Island Marine Science Center
- Daffin Park




