Holiday rentals with a pool in Hilton Head Island

Prime Spot: Harbour, Dining, Shops & Beach

Stay in the heart of it all at this upscale, centrally located guest suite (256 sq ft) with independent entrance, total privacy, queen bed and full bath (no kitchen). Step outside to waterfront restaurants, live music, bars, shops, and summer weekly fireworks. Supermarkets and more dining are just a 10-minute walk away. Enjoy a free shuttle to attractions within 2-mile radius (April–September). Golfing, biking, fishing, and water sports all nearby, free access to Palmetto Dunes Beach community.

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

This beautifully decorated top floor condo provides all the comforts of home. When you open the door, you will see breathtaking views of the Atlantic Ocean. It is located in the heart of the south end of the island steps away to restaurants, shopping and the pristine Coligny beach. The Lost tiki lounge is locally owned and managed. I inspect the unit prior to every guest to ensure it is spotless. I am always available for any needs during your stay, I hope to host you! (Reno happening Nov 2026)

Ocean Front Resort Villa

Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much 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!

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.

Oceanfront Breathtaking Views

Gorgeous Ocean front views await your perfect vacation at this beautifully decorated beach condo in Palmetto Dunes. Five star rated condo features lush landscaping, palm trees, and tropical flowers will entice your senses. Amenities nearby, swimming pools, barbecue grill, hot tub, white sandy beaches, bike cruisers, kayak, pickle ball, golf, fishing and tennis await you. Your condo features a spacious 1 bedroom, 2 bathrooms , kitchen, dining, living room, and balcony for your comfort .

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**

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.

5 Star Location! Pool, Walk to Shops/Dining

This luxury villa is in the heart of Hilton Head Island: Harbour Town in the world famous Sea Pines Resort- home of the PGA Heritage golf tournament! Walk to shopping, lighthouse, dining, water sports, golf, tennis, entertainment, and boat charters! The complimentary, seasonal beach shuttle picks up at the villa and drops off at the Sea Pines Beach Club. Impeccably appointed and sparkling clean with lagoon views. The complex has a private pool and clay tennis courts.

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!

No Stairs, 2/2 Condo, Easy Walk to Beach & Coligny

Enjoy a nice, relaxing stay at Surf Court Villa 65. With a community pool, beach access across the street, a half mile walk to Coligny, and Lowcountry Celebration park around the corner, you are ensured a good time. The 2 bed, 2 bath condo has no stairs which makes for an easy stay for those with small children and mobility challenges. The space offers all of the basics of home with the added incentive of beach life. Beach gear included.