Hilton Head Island waterfront stays

357 waterfront vacation rentals around Hilton Head Island, SC from Whimstay, from $66 a night. Every one is on the water by its own description: beachfront, gulf front, bayfront, canal front or lakefront.

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 289 to 336 of 357, page 7 of 8. Best rated first, then price.

Hilton Head Island waterfront stays

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

Oceanfront Condo with Shared Pool, Hot Tub, Beach Access & Playground

1609 Port Villa

Amazing oceanfront 2BR 2BA 1st floor condo with pool, hot tub, tennis, fitness area, & WD

Peaceful Oceanfront Villa with Pools, Hot Tub, Tennis, & Ocean View

2BR Beach Villa with Balcony Pool Tennis Access

Oceanfront condo with a washer, dryer, central AC, pool, hot tub & beach access

231 Breakers

Quiet Waterfront Condo with WiFi - Pools & Hot Tub On-Site

A Quiet Beach Getaway with Pools, Hot Tub, Tennis Courts, and Private Patio

First Floor, Oceanfront Condo with Free WiFi, Balcony, Shared Hot Tub, Pool, Sauna

Oceanfront Condo with Ocean View, Shared Pool Hot Tub, and Nearby Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

A Relaxing Getaway with Shared Pools and Hot Tub in an Oceanfront Villa

Admiral's Row 130

Splendid condo, pool, full kitchen, & patio

Spacious updated oceanfront condo with shared pools, hot tub & beach access

Oceanfront condo with pools, hot tubs, WiFi, washer, dryer, & central AC

Luxury Villa Rooftop Pool near Beach Hilton Head

Beachfront escape with pools, hot tub, WiFi, washer dryer, & central AC

Beachfront getaway with WiFi, pools, hot tub, gym, washer dryer, & central AC

Ocean view condo at beachfront resort with pool, hot tub, pickleball & tennis

Coastal condo on the beach with panoramic views, beach access & a shared pool

Upgraded condo on waterfront with pool, hot tub, & tennis access - near beach

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

Oceanfront Villa with Shared Pools, Hot tub, and Beach Access

Charming waterfront resort condo with pool, tennis, golf, & balcony

Cozy oceanfront villa, tennis courts, hot tub, shared pool and ocean view

Newly-renovated ocean front condo on the 5th floor with a private balcony