Hilton Head Island waterfront stays

337 waterfront vacation rentals in Hilton Head Island, SC from Whimstay, from $66 a night, each on the water by its own description. Part of our Hilton Head Island coverage.

Rates are each listing's own "from" price on 4 August 2026; the booking page shows live prices and dates. Looking for the houses we would book ourselves? The curated Hilton Head Island list.

Showing 241 to 288 of 337, page 6 of 8. Best rated first, then price.

Hilton Head Island waterfront stays

Oceanview 4th Floor. 2BR Beach & Tennis Villa

Seaside 247

Waterfront villa with resort amenities, beach access, open layout, AC, & WD

Beachfront Villa W/ Pool & Tennis Hilton Head

Pet-Friendly Inverness Villa on Golf Course

2BR Queen's Grant Villa in Palmetto Dunes, Modern Furnishings, Prime Location, Community Pool!

Condo near beach with 2 pools, restaurants, gym, 6 tennis, 12 pickleball, W D

Waterfront condo with walkable locale, central AC, washer dryer, & shared pool

Hilton Head Beach & Tennis Resort, Oceanfront, Tennis, Restaurants, Pickleball!

Pet Friendly Villa with Patio, Pool, + Nearby Golf

Seaside 278

Open and Airy 3 Bed 2 Bath St Andrews Villa

Second-floor condo in beachfront complex with pools, tennis & gym

Oceanfront condo with WiFi, pool, hot tub & beach access

Spacious Patio and Community Pool - Elegant Coastal Hideaway

Spacious Villa with Balcony and Resort Amenities - Elegant Coastal Haven

Beachfront Getaway. Pool, Tennis + Ocean Air

Spacious Villa with Scenic Balcony and Resort Access - Stylish Coastal Haven

Coastal Escape w/ Pool & Ocean Peek!

Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly

Waterfront Condo with Shared Pools, Hot Tubs, Private Balconies, and Ocean Views

Fully Equipped Kitchen and Resort Amenities Await - Spacious Villa Retreat

Beachfront condo w pool, tennis and pickleball, gym & balcony

Beach-view condo in oceanfront complex with outdoor pool, beach access, balcony

Waterfront condo with seasonal pools, hot tub, balcony, AC, & WD

Scenic Balcony and Resort Amenities - Charming Villa Retreat

Waterfront Condo with Ocean Views, Shared Pool, Hot Tub, and Covered Balcony

Seaside 358

Beach-view condo in oceanfront complex with outdoor pool, beach access & balcony

Oceanfront, 3rd floor villa with corner balcony, pool and beach access

Panoramic Views and Luxurious Amenities - Stunning Oceanfront Retreat

Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort

Calming Condo Getaway with Shared Pool, Hot Tub, and Tennis Courts

Waterfront condo with amazing views, on-site pool, hot tub, & gym

Stunning Views and Resort Amenities - Charming Oceanfront Haven

Updated, waterfront condo with amazing lagoon & golf views from the sunroom

Newly renovated beachfront condo with pool, tennis, restaurants, gym, & balcony

Tennis Villas B04

Tennis Villas F09

Waterfront, dog-friendly Villa at Shelter Cove with pool, deck & harbor view

Coastal Views and Direct Beach Access - Stunning Beachfront Retreat

Beach-view condo in oceanfront complex with outdoor pool, beach access & balcony

Gorgeous Oceanfront Villa, w/ Pool on Hilton Head

Dreamy condo on the beach with balcony view, shared pool, & charming decor

Oceanfront villa with WiFi, full kitchen, pool, & hot tub - beach nearby

Beachfront Getaway! Hilton Head Resort Condo

Oceanfront Villa with Shared Pool, Hot Tub, Ocean Views, and More - Beach Nearby

309 Breakers