Under $250 stays in Hilton Head Island

240 under $250 a night rentals around 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 145 to 192 of 240, page 4 of 5. Best rated first, then price.

Family-Friendly Condo w/ Pools + Tennis Courts!, Hilton Head Island, SC from $209

Family-Friendly Condo w/ Pools + Tennis Courts!

Oceanfront Entire condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.5
Oceanfront Villa and Stunning Views - Luxurious Coastal Retreat, Hilton Head Island, SC from $247

Oceanfront Villa and Stunning Views - Luxurious Coastal Retreat

Oceanfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.5
Pet Friendly Villa, Pool Beach & Golf! Hilton Head, Hilton Head Island, SC from $125

Pet Friendly Villa, Pool Beach & Golf! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 8 pets ok
Hilton Head Island, SCrated 4.4
Waterfront Villa w/ Dock Near Beach on Hilton Head, Hilton Head Island, SC from $199

Waterfront Villa w/ Dock Near Beach on Hilton Head

Waterfront Condo 3 bed 3 bath sleeps 6 pets ok
Hilton Head Island, SCrated 4.4
Oceanfront Access and Community Pool - Beautiful Coastal Villa, Hilton Head Island, SC from $205

Oceanfront Access and Community Pool - Beautiful Coastal Villa

Oceanfront Villa 2 bed 2 bath sleeps 5
Hilton Head Island, SCrated 4.4
Long-Term Stays Welcome: HH Island Resort Condo, Hilton Head Island, SC from $206

Long-Term Stays Welcome: HH Island Resort Condo

Oceanfront Entire condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.4
Waterfront Villa! Near Pool & Tennis, Hilton Head, Hilton Head Island, SC from $91

Waterfront Villa! Near Pool & Tennis, Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.3
Fun Oceanfront Villa w/ Pool on Hilton Head, Hilton Head Island, SC from $107

Fun Oceanfront Villa w/ Pool on Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.3
Beach Access: Oceanfront Hilton Head Studio, Hilton Head Island, SC from $136

Beach Access: Oceanfront Hilton Head Studio

Oceanfront Entire loft 1 bath sleeps 4
Hilton Head Island, SCrated 4.3
Beachfront Villa W/ Pool & Tennis Hilton Head, Hilton Head Island, SC from $100

Beachfront Villa W/ Pool & Tennis Hilton Head

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.0
Beachside Condo with Shared Pool & Private Balcony Retreat, Hilton Head Island, SC from $116

Beachside Condo with Shared Pool & Private Balcony Retreat

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.0
Dream Getaway w/ wraparound deck on Hilton Head!, Hilton Head Island, SC from $117

Dream Getaway w/ wraparound deck on Hilton Head!

Oceanfront Condo 2 bed 2 bath sleeps 5 pets ok
Hilton Head Island, SCrated 4.0
Compare before you book

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Ocean Views and Three Pools - Serene Beachfront Sanctuary, Tybee Island, GA from $120

Ocean Views and Three Pools - Serene Beachfront Sanctuary

Beachfront Condo 2 bed 2 bath sleeps 6
Tybee Island, GArated 4.0
Balcony, Ocean Access and Spacious Living Area - Charming Coastal Haven, Hilton Head Island, SC from $124

Balcony, Ocean Access and Spacious Living Area - Charming Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 5
Hilton Head Island, SCrated 4.0
Oceanfront Resort with Tennis Pool Spa, Hilton Head Island, SC from $137

Oceanfront Resort with Tennis Pool Spa

Oceanfront Apartment 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.0
Harbourfront Condo in Harbour Town, Hilton Head Island, SC from $152

Harbourfront Condo in Harbour Town

Harbor front Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.0
Beach & Pool Access: Tranquil Hilton Head Getaway, Hilton Head Island, SC from $203

Beach & Pool Access: Tranquil Hilton Head Getaway

Beachfront Entire condo 2 bed 2 bath sleeps 5
Hilton Head Island, SCrated 4.0
Ocean Villas C346, Hilton Head Island, SC from $243

Ocean Villas C346

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.0
Home, 7 Miles to Savannah Historic District!, Savannah, GA from $158

Home, 7 Miles to Savannah Historic District!

Waterfront Entire home 3 bed 2 bath sleeps 6
Savannah, GArated 3.8
Pool, Spa & Dining: Beach Condo in Hilton Head!, Hilton Head Island, SC from $107

Pool, Spa & Dining: Beach Condo in Hilton Head!

Beachfront Entire condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 3.7
Community Swimming Pool and Free Bikes - Charming Island Haven, Hilton Head Island, SC from $208

Community Swimming Pool and Free Bikes - Charming Island Haven

Oceanfront Villa 2 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 3.7
Top Floor Condo at Beach & Tennis Resort Beachfront Pool & Golf access, Hilton Head Island, SC from $87

Top Floor Condo at Beach & Tennis Resort Beachfront Pool & Golf access

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 3.0
Panoramic Views and Luxurious Features - Stunning Oceanfront Villa, Hilton Head Island, SC from $136

Panoramic Views and Luxurious Features - Stunning Oceanfront Villa

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 3.0
Pool Access! Oceanfront Hilton Head Island Condo, Hilton Head Island, SC from $160

Pool Access! Oceanfront Hilton Head Island Condo

Oceanfront Entire condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 3.0
Pet Friendly Waterfront Villa w/ Dock, Hilton Head, Hilton Head Island, SC from $178

Pet Friendly Waterfront Villa w/ Dock, Hilton Head

Waterfront Condo 3 bed 3 bath sleeps 6 pets ok
Hilton Head Island, SCrated 3.0
Beachfront villa near golf with pool, hot tub, & balcony - snowbird-friendly, Hilton Head Island, SC from $66

Beachfront villa near golf with pool, hot tub, & balcony - snowbird-friendly

Beachfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SC
Oceanfront resort condo with WiFi, balcony, pool, grills, & beach access, Hilton Head Island, SC from $78

Oceanfront resort condo with WiFi, balcony, pool, grills, & beach access

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
3rd Floor Condo with pools, tennis/pickleball courts, access to beach, Hilton Head Island, SC from $79

3rd Floor Condo with pools, tennis/pickleball courts, access to beach

Beachfront Condo 2 bed 2 bath sleeps 4
Hilton Head Island, SC
Secluded & Peaceful - Vacation Getaway with WiFi, Pool, Hot Tub, & Private Beach, Hilton Head Island, SC from $97

Secluded & Peaceful - Vacation Getaway with WiFi, Pool, Hot Tub, & Private Beach

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi, Hilton Head Island, SC from $98

Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi

Bayfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SC
Spacious condo with pool, tennis courts, & golf on-site, Hilton Head Island, SC from $98

Spacious condo with pool, tennis courts, & golf on-site

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
Oceanview 4th Floor. 2BR Beach & Tennis Villa, Hilton Head Island, SC from $98

Oceanview 4th Floor. 2BR Beach & Tennis Villa

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SC
Seaside 247, Hilton Head Island, SC from $100

Seaside 247

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
Waterfront villa with resort amenities, beach access, open layout, AC, & WD, Hilton Head Island, SC from $104

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, Hilton Head Island, SC from $110

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, Hilton Head Island, SC from $111

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!, Hilton Head Island, SC from $116

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, Hilton Head Island, SC from $116

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, Hilton Head Island, SC from $117

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!, Hilton Head Island, SC from $117

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, Hilton Head Island, SC from $118

Pet Friendly Villa with Patio, Pool, + Nearby Golf

Beachfront Condo 2 bed 1 bath sleeps 5 pets ok
Hilton Head Island, SC
Seaside 278, Hilton Head Island, SC from $119

Seaside 278

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
Open and Airy 3 Bed 2 Bath St Andrews Villa, Hilton Head Island, SC from $121

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, Hilton Head Island, SC from $122

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, Hilton Head Island, SC from $122

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

Oceanfront Condo 2 bed 2 bath sleeps 5
Hilton Head Island, SC
Spacious Patio and Community Pool - Elegant Coastal Hideaway, Hilton Head Island, SC from $123

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, Hilton Head Island, SC from $123

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, Hilton Head Island, SC from $124

Beachfront Getaway. Pool, Tennis + Ocean Air

Beachfront Condo 2 bed 2 bath sleeps 5
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 →
Every shore

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

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