Holiday rentals in Sea Pines

Flat in Hilton Head Island

5 out of 5 average rating, 23 reviews

Sea Pines Villa – Walk to Beach, Pool, & Salty Dog

Steps from Beach, Pool, & Salty Dog! Bright 3-bed villa in the heart of Sea Pines fast Wi-Fi and fully stocked kitchen. What you’ll love: 5-minute walk to sand, trails & marina dining Large open living area with Smart TV & books Private patio for morning coffee under palms Enjoy full-size washer/dryer, beach gear and free on-site parking. Ideal for families or couples wanting space to relax after sun-soaked days. Ready for a carefree coastal getaway? Tap “Reserve” before your dates disappear!

Townhouse in Hilton Head Island

A spacious entryway greets guests with a view of the open-plan living area, featuring a mix of comfortable seating options. A staircase leads to the upper level, while large windows allow natural light to fill the space, creating a bright and inviting atmosphere.

4.88 out of 5 average rating, 16 reviews

Luxurious 3BR Townhome with Golf Views

Welcome to this luxurious 3-bedroom townhome located in Sea Pines Resort, Hilton Head Island. - Coastal-chic interiors for a stylish atmosphere. - Three en suite bedrooms for privacy. - Fully equipped kitchen and high-speed Wi-Fi. - Private patio with grill and golf course views. - Access to two pools for relaxation. - Excellent location short bike ride to beach or harbor town or south beach marina. Your dream vacation awaits in this elegant townhome where comfort meets charm.

Home in Hilton Head Island

A community pool area is surrounded by lush greenery, featuring a large swimming pool with a gentle slope and steps for easy access. Several lounge chairs are positioned around the pool, providing relaxation spots, while a shaded area with umbrellas is visible. Safety floats are present in the water.

5 out of 5 average rating, 29 reviews

Sea Pines Serenity!

LOCATION, LOCATION, LOCATION! If you want security and serenity, this home is for you! This stylish 3 bed, 2 bath house has EVERYTHING you need for a relaxing vacation. Walking distance (10 blocks) to the best beaches on the island, dozens of restaurants and amazing Harbour Town! The fabulous Beach Club has onsite parking Sea Pines guests. Spend the day on a dolphin or pirate cruise, and then spend the night relaxing on a huge patio with your fire pit while enjoying s’mores!

A spacious living area is illuminated by natural light, featuring a large flat-screen TV and a wooden coffee table. Seating includes a plush sofa, loveseat, and a comfortable chair. A desk with two stools provides additional workspace, and the adjacent kitchen is partially visible.

5 out of 5 average rating, 43 reviews

Luxury Penthouse in the Heart of Harbour Town

We offer a weekly a 10% off 7 nights or more. Discount is automatically applied. Plan your next vacation in this luxurious villa. It’s prime location is steps from Hilton Head’s iconic lighthouse, marina, shops and restaurants. There are only 9 villas in the this building. This unit is on the top floor on the end closest to the marina. If you are familiar with Harbour Town, Mariner’s Way is located between the live oak trees on the sandy playground and the Crazy Crab.

Luxe

Villa in Hilton Head Island

5 out of 5 average rating, 8 reviews

100 Fairway Lane, Sea Pines: A Luxury Villa Stay

Welcome to all NEW BESTNEST/Luxe: An Elevated Experience in Vacationing, and our newest Luxe property at Unit 100 Fairway Lane Villas in Sea Pines. (200 Fairway Lane for mapping) Enjoy the ultimate in vacation rental accommodations on Hilton Head Island, featuring a carefully curated collection of homes and villas, chosen with the discerning traveler in mind, fabulously stocked, outfitted, and equipped, and supported by your personal property concierge, available 24/7.

5 out of 5 average rating, 108 reviews

5 Star Location-Pool, Walk to Dining/Shops/Marina

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.

Flat in Hilton Head Island

A bright living room features a white sofa set adorned with colorful cushions. A modern ceiling fan is visible above, while a flat-screen television is mounted against a blue accent wall. A coffee table is positioned in the center, complemented by an area rug and outdoor views through large windows.

4.89 out of 5 average rating, 18 reviews

SeaPines-Stunning & Pet Friendly

Enjoy a Stylish Coastal Dream! We are pleased to welcome 35 Lighthouse back to the rental market after undergoing a breathtaking complete remodel. Everything is new, from the kitchen and baths to furnishings, and all finishes were done with taste and care. Open concept, spacious and with an amazing golf view, this 2 bedroom in Seapines couples the perfect location (1/2 mile to the Beach Club and a mile to Harbour Town) and comfort. All of this and pet friendly!

An outdoor dining area is shown, featuring a round table with six ornate metal chairs. A large red umbrella provides shade, and lush greenery and a view of the marina are visible in the background.

4.98 out of 5 average rating, 185 reviews

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

In the Heart of Harbour Town Experience the best of Harbour Town living with exquisite harbour views in this recently updated 2 BR / 2.5 BA end unit just steps away from the waterfront. Villa is a short walk to pool, the pristine Harbour Town Golf Links, and the Sea Pines Trolley -- offering complimentary seasonal transport. Recently renovated with gourmet kitchen, elegant living area, and outdoor dining. Sleeps 8. Includes Harbour Town pool passes.

A spacious master bedroom features a King-size bed with white linens and soft gray accents. Natural light enters through a large window covered by sheer curtains. A wooden dresser and artwork add a touch of warmth to the neutral-toned space.

5 out of 5 average rating, 31 reviews

Spacious Harbor Town Condo!

Your perfect vacation begins when you walk out the door of this newly renovated condo into the Harbour Town marina with its boutique shops, gourmet restaurants, racquet club offering tennis and pickleball, famous PGA tournament golf course, and the iconic red and white lighthouse. The spacious 1-BR sleeps up to four guests. The master bedroom has a King-size bed and a large picture window that comes with blackout curtains for late sleepers.

Treehouse in Hilton Head Island

A bright living area is highlighted by a sleek electric fireplace and a mounted TV, creating a modern and inviting space. A comfortable sofa with decorative cushions provides ample seating. Natural light streams in through large windows, enhancing the airy feel of the room.

5 out of 5 average rating, 17 reviews

Roxy’s Hideaway | Harbour Town RBC Heritage Oasis

Roxy’s Hideaway — #1 Sea Pines Treehouse, steps from Harbour Town & RBC Heritage! Enjoy exclusive comfort in nature, close to shopping, dining and more. Pet-friendly and ideal for high-end travelers, including pro athletes. Experience unmatched service and bespoke amenities—now including an EV charger. Relax in our hammock throne, surrounded by nature and serene unaugmented ocean views, with pool access at the Harbour Town Pool!

5 out of 5 average rating, 13 reviews

MyStay at 1029 Caravel | Lighthouse Views & Pool!

Escape to 1029 Caravel Court, a dreamy Harbour Town getaway with front-row marina views, a king-size zero-gravity bed, and luxe coastal touches. Sip wine on the balcony, stroll to shops, or unwind at the Harbour Town Pool, a 120-ft freeform pool, heated and cooled seasonally. Plush linens, beach gear, & 24/7 service make every moment effortless. Love, luxury, and lighthouse views—book now!