Under $150 stays in Hilton Head Island
129 under $150 a night rentals in Hilton Head Island, SC, from $66 a night.
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 97 to 129 of 129, page 3 of 3. Best rated first, then price.
Waterfront villa with resort amenities, beach access, open layout, AC, & WD
Waterfront
Villa
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Beachfront Villa W/ Pool & Tennis Hilton Head
Beachfront
Condo
1 bed
1 bath
sleeps 6
Hilton Head Island, SC
Pet-Friendly Inverness Villa on Golf Course
Oceanfront
Condo
2 bed
2 bath
sleeps 6
pets ok
Hilton Head Island, SC
2BR Queen's Grant Villa in Palmetto Dunes, Modern Furnishings, Prime Location, Community Pool!
Oceanfront
Villa
2 bed
1 bath
sleeps 7
pets ok
Hilton Head Island, SC
Condo near beach with 2 pools, restaurants, gym, 6 tennis, 12 pickleball, W D
Beachfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Waterfront condo with walkable locale, central AC, washer dryer, & shared pool
Waterfront
Condo
2 bed
2 bath
sleeps 7
Hilton Head Island, SC
Hilton Head Beach & Tennis Resort, Oceanfront, Tennis, Restaurants, Pickleball!
Oceanfront
Condo
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Pet Friendly Villa with Patio, Pool, + Nearby Golf
Beachfront
Condo
2 bed
1 bath
sleeps 5
pets ok
Hilton Head Island, SC
Seaside 278
Oceanfront
Condo
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Open and Airy 3 Bed 2 Bath St Andrews Villa
Oceanfront
Condo
2 bed
2 bath
sleeps 6
pets ok
Hilton Head Island, SC
Second-floor condo in beachfront complex with pools, tennis & gym
Beachfront
Condo
1 bed
1 bath
sleeps 6
Hilton Head Island, SC
Oceanfront condo with WiFi, pool, hot tub & beach access
Oceanfront
Condo
2 bed
2 bath
sleeps 5
Hilton Head Island, SC
Compare before you book
See Hilton Head Island on Vrbo, with dates and live prices.
Search Vrbo → Booking.com → Affiliate links.Spacious Patio and Community Pool - Elegant Coastal Hideaway
Oceanfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Spacious Villa with Balcony and Resort Amenities - Elegant Coastal Haven
Beachfront
Condo
1 bed
1 bath
sleeps 6
Hilton Head Island, SC
Beachfront Getaway. Pool, Tennis + Ocean Air
Beachfront
Condo
2 bed
2 bath
sleeps 5
Hilton Head Island, SC
Spacious Villa with Scenic Balcony and Resort Access - Stylish Coastal Haven
Beachfront
Condo
1 bed
1 bath
sleeps 6
Hilton Head Island, SC
Coastal Escape w/ Pool & Ocean Peek!
Beachfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly
Bayfront
Condo
3 bed
2 bath
sleeps 10
Hilton Head Island, SC
Waterfront Condo with Shared Pools, Hot Tubs, Private Balconies, and Ocean Views
Waterfront
Condo
2 bed
2 bath
sleeps 8
Hilton Head Island, SC
Fully Equipped Kitchen and Resort Amenities Await - Spacious Villa Retreat
Beachfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Beachfront condo w pool, tennis and pickleball, gym & balcony
Beachfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Beach-view condo in oceanfront complex with outdoor pool, beach access, balcony
Oceanfront
Condo
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Waterfront condo with seasonal pools, hot tub, balcony, AC, & WD
Waterfront
Condo
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Scenic Balcony and Resort Amenities - Charming Villa Retreat
Beachfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Waterfront Condo with Ocean Views, Shared Pool, Hot Tub, and Covered Balcony
Waterfront
Condo
1 bed
2 bath
sleeps 4
Hilton Head Island, SC
Seaside 358
Oceanfront
Condo
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Beach-view condo in oceanfront complex with outdoor pool, beach access & balcony
Oceanfront
Condo
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Oceanfront, 3rd floor villa with corner balcony, pool and beach access
Oceanfront
Villa
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Panoramic Views and Luxurious Amenities - Stunning Oceanfront Retreat
Oceanfront
Condo
1 bed
1 bath
sleeps 6
Hilton Head Island, SC
Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort
Oceanfront
Villa
1 bed
1 bath
sleeps 4
Hilton Head Island, SC
Calming Condo Getaway with Shared Pool, Hot Tub, and Tennis Courts
Oceanfront
Condo
2 bed
2 bath
sleeps 7
Hilton Head Island, SC
Waterfront condo with amazing views, on-site pool, hot tub, & gym
Waterfront
Condo
2 bed
2 bath
sleeps 6
Hilton Head Island, SC
Stunning Views and Resort Amenities - Charming Oceanfront Haven
Oceanfront
Condo
1 bed
1 bath
sleeps 6
Hilton Head Island, SC
The curated list
Hilton Head Island the way we would book it: a short list of houses we checked for real water access.
Open the Hilton Head Island guide →Affiliate disclosure: Sleep By The Beach earns a commission when you book through Whimstay, Vrbo or Booking.com links on this page, at no extra cost to you. Listing details and photos come from the Whimstay feed and belong to the hosts. How we work.