Under $250 stays in Hilton Head Island

231 under $250 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 1 to 48 of 231, page 1 of 5. Best rated first, then price.

Renovated condo on the beach with pool, balcony, central AC, W D, & fitness room, Hilton Head Island, SC from $77

Renovated condo on the beach with pool, balcony, central AC, W D, & fitness room

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Modern Ocean Villa A204. Renovated & Bright, Hilton Head Island, SC from $93

Modern Ocean Villa A204. Renovated & Bright

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Waterfront condo with private balcony, W D and near beach and marina, Hilton Head Island, SC from $95

Waterfront condo with private balcony, W D and near beach and marina

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Nautical touches abound at this renovated waterfront condo with pool & tennis, Hilton Head Island, SC from $98

Nautical touches abound at this renovated waterfront condo with pool & tennis

Waterfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Beachfront Villa W/ Pool & Tennis Hilton Head, Hilton Head Island, SC from $101

Beachfront Villa W/ Pool & Tennis Hilton Head

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Beachside Bliss, Newly Renovated, Pet Friendly, Hilton Head Island, SC from $102

Beachside Bliss, Newly Renovated, Pet Friendly

Waterfront Condo 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
736 Queens Grant @ Palmetto Dunes. Updated Condo. Prime Location, Hilton Head Island, SC from $106

736 Queens Grant @ Palmetto Dunes. Updated Condo. Prime Location

Oceanfront Condo 2 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Admiral's Row. 3rd Floor Gem. Beachfront Balcony, Hilton Head Island, SC from $106

Admiral's Row. 3rd Floor Gem. Beachfront Balcony

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Cozy Retreat with Oceanfront Pool and Tennis Courts - Charming Escape, Hilton Head Island, SC from $111

Cozy Retreat with Oceanfront Pool and Tennis Courts - Charming Escape

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Charming Villa with Outdoor Courtyard - Cozy Coastal Escape, Hilton Head Island, SC from $111

Charming Villa with Outdoor Courtyard - Cozy Coastal Escape

Oceanfront Condo 2 bed 1 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
Balcony, Pool Access and Tennis Courts - Charming Coastal Retreat, Hilton Head Island, SC from $116

Balcony, Pool Access and Tennis Courts - Charming Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Oceanfront Pool and Hot Tub - Elegant Coastal Escape, Hilton Head Island, SC from $118

Oceanfront Pool and Hot Tub - Elegant Coastal Escape

Oceanfront Villa 1 bed 1.5 bath sleeps 4
Hilton Head Island, SCrated 5.0
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Queens Grant 655, Hilton Head Island, SC from $118

Queens Grant 655

Oceanfront Condo 2 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Pool Access - Charming Coastal Getaway, Hilton Head Island, SC from $119

Spacious Villa with Balcony and Pool Access - Charming Coastal Getaway

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Renovated Coastal Villa, Pet Friendly! Hilton Head, Hilton Head Island, SC from $120

Renovated Coastal Villa, Pet Friendly! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 4 pets ok
Hilton Head Island, SCrated 5.0
Steps to Beach! 2BR Oceanfront Pool, Private Balcony & Coastal Charm, Hilton Head Island, SC from $121

Steps to Beach! 2BR Oceanfront Pool, Private Balcony & Coastal Charm

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony, Pool, and Tennis Court Access - Spacious Coastal Haven, Hilton Head Island, SC from $121

Balcony, Pool, and Tennis Court Access - Spacious Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Ocean Access and Elegant Amenities - Charming Coastal Haven, Hilton Head Island, SC from $121

Ocean Access and Elegant Amenities - Charming Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Elegant Villa w/ Pool, Golf & Beach, Hilton Head, Hilton Head Island, SC from $122

Elegant Villa w/ Pool, Golf & Beach, Hilton Head

Oceanfront Condo 2 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Fully Equipped Kitchen and Access to Pool and Beach - Spacious Coastal Haven, Hilton Head Island, SC from $122

Fully Equipped Kitchen and Access to Pool and Beach - Spacious Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Resort Amenities - Charming Coastal Haven, Hilton Head Island, SC from $122

Spacious Villa with Balcony and Resort Amenities - Charming Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Scenic Balcony and Access to Pools - Charming Coastal Getaway, Hilton Head Island, SC from $123

Scenic Balcony and Access to Pools - Charming Coastal Getaway

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony and Access to Stunning Beach Activities - Beautiful Coastal Haven, Hilton Head Island, SC from $124

Balcony and Access to Stunning Beach Activities - Beautiful Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Balcony, Pool Access and Tennis Courts - Charming Coastal Oasis, Hilton Head Island, SC from $124

Balcony, Pool Access and Tennis Courts - Charming Coastal Oasis

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Scenic Balcony and Fully Equipped Kitchenette - Charming Coastal Retreat, Hilton Head Island, SC from $124

Scenic Balcony and Fully Equipped Kitchenette - Charming Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Private Balcony and Resort Amenities - Beautiful Coastal Retreat, Hilton Head Island, SC from $124

Private Balcony and Resort Amenities - Beautiful Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony, Pool Access and Tennis Courts - Spacious Coastal Haven, Hilton Head Island, SC from $125

Balcony, Pool Access and Tennis Courts - Spacious Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat, Hilton Head Island, SC from $125

Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat

Oceanfront Condo 3 bed 3 bath sleeps 12 pets ok
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Resort Amenities - Charming Coastal Escape, Hilton Head Island, SC from $125

Spacious Villa with Balcony and Resort Amenities - Charming Coastal Escape

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony and Access to Resort Amenities - Spacious Coastal Retreat, Hilton Head Island, SC from $126

Balcony and Access to Resort Amenities - Spacious Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Fairytale Escape w/ Pool, Tennis Golf Hilton Head, Hilton Head Island, SC from $131

Fairytale Escape w/ Pool, Tennis Golf Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4 pets ok
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Resort Amenities - Charming Beach Haven, Hilton Head Island, SC from $136

Spacious Villa with Balcony and Resort Amenities - Charming Beach Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Panoramic Views and Luxurious Amenities - Gorgeous Oceanfront Escape, Hilton Head Island, SC from $137

Panoramic Views and Luxurious Amenities - Gorgeous Oceanfront Escape

Oceanfront Condo 1 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Oceanfront Retreat 318 Breakers, Hilton Head Island, SC from $138

Oceanfront Retreat 318 Breakers

Oceanfront Villa 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Furnished Balcony and Access to Tennis Courts and Pool - Charming Coastal Retreat, Hilton Head Island, SC from $141

Furnished Balcony and Access to Tennis Courts and Pool - Charming Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 2
Hilton Head Island, SCrated 5.0
Beachfront condo with large furnished balcony, pool & beautiful views, Hilton Head Island, SC from $145

Beachfront condo with large furnished balcony, pool & beautiful views

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Coastal Luxury! Pool, Golf, Beach Hilton Head, Hilton Head Island, SC from $148

Coastal Luxury! Pool, Golf, Beach Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7 pets ok
Hilton Head Island, SCrated 5.0
Palmetto Dunes Chic 2BR Villa Pickleball Golf Pool, Hilton Head Island, SC from $150

Palmetto Dunes Chic 2BR Villa Pickleball Golf Pool

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Coastal Chic Villa Near Beach and Shops, Hilton Head Island, SC from $156

Coastal Chic Villa Near Beach and Shops

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Forest Beach Condo. Community Pool. Oceanfront Private Beach Access. Elegant Furnishings, Hilton Head Island, SC from $163

Forest Beach Condo. Community Pool. Oceanfront Private Beach Access. Elegant Furnishings

Oceanfront Condo 2 bed 2 bath sleeps 4
Hilton Head Island, SCrated 5.0
Luxury Villa Golf Beach & Pool Access Hilton Head, Hilton Head Island, SC from $165

Luxury Villa Golf Beach & Pool Access Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Oceanfront Resort. Newly Renovated 1BR Villa, Hilton Head Island, SC from $165

Oceanfront Resort. Newly Renovated 1BR Villa

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Admiral's Row 339, Hilton Head Island, SC from $167

Admiral's Row 339

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Spacious Patio and Community Pool Access - Charming Family Retreat, Hilton Head Island, SC from $169

Spacious Patio and Community Pool Access - Charming Family Retreat

Oceanfront Condo 3 bed 2 bath sleeps 9
Hilton Head Island, SCrated 5.0
Breathtaking Views and Resort Amenities - Gorgeous Oceanfront Villa, Hilton Head Island, SC from $176

Breathtaking Views and Resort Amenities - Gorgeous Oceanfront Villa

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Escape with Stunning Views and Pool - Serene Coastal Retreat, Hilton Head Island, SC from $179

Oceanfront Escape with Stunning Views and Pool - Serene Coastal Retreat

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Breakers 137 Condo w/ Sunrise Views!, Hilton Head Island, SC from $180

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Entire condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
7447 Anchorage, Hilton Head Island, SC from $180

7447 Anchorage

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
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 →
Every shore

Ten shores, each with its own stays list and curated picks.

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