Stays for 8+ guests in Hilton Head Island, SC
Stays for 8+ guests in Hilton Head Island, SC, from $80 a night. Book direct on each manager's site, no OTA fee.
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HHI Resort 2BR | Beach Walk, Pools & Gym | For 8
Condo · 2 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $80 a night
- air conditioning
- baking sheet
- bathtub
- bbq grill
Exact location
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Queens Grant Villa on Golf Course w Shared Pool!
Villa · 3 bed · 2 bath · sleeps 10
Hilton Head Island, SC
From $95 a night
- air conditioning
- baking sheet
- barbeque utensils
- bathtub
Exact location
Book direct on Prime Vacation Rentals Across the U.S. & Hawaii
3BR Sleeps 8, Walk to Beach, Pool Access!
Condo · 3 bed · 2 bath · sleeps 8
Hilton Head Island
From $105 a night
- air conditioning
- baking sheet
- barbeque utensils
- bathtub
Exact location
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Stunning Lagoon View Rental Home in Sea Pines, HHI
House · 3 bed · 2 bath · sleeps 8
Hilton Head Island
From $157 a night
- air conditioning
- baking sheet
- barbeque utensils
- bathtub
Exact location
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Spacious Condo in the Heart of Hilton Head
Apartment · 2 bed · 3 bath · sleeps 8
From $187 a night
- team up with experts
- custom listing creation
- guest screening and virtual front desk
- 24/7 reservation and payment processing
Exact location
Book direct on hosteeva.com
4BR, 3BA, Near Folly Field Beach, Sleeps 18
House · 4 bed · 3 bath · sleeps 18
Hilton Head Island, SC
From $188 a night
- air conditioning
- baking sheet
- beach
- beach access
Exact location
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5BR Home for 12 w/ Private Pool, Near Beach!
House · 5 bed · 3 bath · sleeps 12
Hilton Head Island, SC
From $219 a night
- air conditioning
- baking sheet
- barbeque utensils
- bbq grill
Exact location
Book direct on Prime Vacation Rentals Across the U.S. & Hawaii
4BR for 8 w/ Shared Pool, Pickleball & Tennis!
Loft · 4 bed · 3 bath · sleeps 8
Hilton Head Island
From $300 a night
- air conditioning
- baking sheet
- barbeque utensils
- bathtub
Exact location
Book direct on Prime Vacation Rentals Across the U.S. & Hawaii
Sandy Beach Retreat - Burkes Beach w Private Pool
House · 9 bed · 6 bath · sleeps 18
Hilton Head Island, SC
From $300 a night
- air conditioning
- baby bath
- baking sheet
- barbeque utensils
Exact location
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Renovated Island Escape W/ Shared Pools, Easy Beach Access, Fast WiFi & Patio
Bungalow · 3 bed · 3 bath · sleeps 8
Hilton Head Island, SC
From $89 a night
- air conditioning
- babysitter recommendations
- beach
- beach access
Exact location
Book direct on CielStay
Second-Floor Villa Near the Beach w/Balcony Views of the Pool & Lagoon
Villa · 3 bed · 3 bath · sleeps 8
Hilton Head Island, SC
From $125 a night
- air conditioning
- babysitter recommendations
- beach
- beach access
Exact location
Book direct on CielStay
Charming Waterfront Getaway with Seasonal Pool & Hot Tub, Tennis, Beach Access
Villa · 3 bed · 3 bath · sleeps 9
Hilton Head Island, SC
From $139 a night
- air conditioning
- bbq grill
- babysitter recommendations
- beach
Exact location
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A Quiet Place
House · 3 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $153 a night
- king bed
- night stands with reading lamps
- armoire with flatscreen tv
Exact location
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Updated coastal villa with pools, athletic courts, gym, smart TVs, AC, & W/D
Villa · 3 bed · 2 bath · sleeps 9
Hilton Head Island, SC
From $200 a night
- air conditioning
- babysitter recommendations
- beach
- beach access
Exact location
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Treetops 4502
Townhome · 3 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $413 a night
- queen size bed
- side tables with lamps
- ceiling fan
- flat screen tv
Exact location
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30 Knotts Way
House · 5 bed · 5 bath · sleeps 18
Hilton Head Island, SC
From $695 a night
- private heated outdoor swimming pool
- garage
- parking option included
- accept credit card
Exact location
Book direct on No Booking Fee Book Direct with Owner Hilton Head Island Vacation Rentals
Cassina Palms
House · 5 bed · 5 bath · sleeps 16
Hilton Head Island, SC
From $895 a night
- private unheated outdoor swimming pool
- parking option included
- parking roofed car port
- accept credit card
Exact location
Book direct on No Booking Fee Book Direct with Owner Hilton Head Island Vacation Rentals
1 Black Duck
Villa · 4 bath · sleeps 12
Hilton Head, SC
From $182 a night
- beach cart
- grill/bbq - private
- hot tub/spa - private
- pool access
Exact location
Book direct on Hilton Head Island Vacations
1 Brown Pelican
Villa · 3.5 bath · sleeps 10
Hilton Head, SC
From $182 a night
- beach cart
- ev charger
- grill/bbq - private
- pool access
Exact location
Book direct on Hilton Head Island Vacations
1 Cartgate
Villa · 4.5 bath · sleeps 10
Hilton Head, SC
From $182 a night
- beach cart
- grill/bbq - private
- hot tub/spa - private
- pool access
Exact location
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1 Roadrunner
Beach house · 4.5 bath · sleeps 13
Hilton Head, SC
From $182 a night
- beach cart
- grill/bbq - private
- hot tub/spa - private
- pool access
Exact location
Book direct on Hilton Head Island Vacations
1 West Garrison
Villa · 4.5 bath · sleeps 12
Hilton Head, SC
From $182 a night
- beach cart
- grill/bbq - private
- hot tub/spa - private
- pool access
Exact location
Book direct on Hilton Head Island Vacations
28 Ruddy Turnstone
Villa · 4 bed · 4.5 bath · sleeps 12
Hilton Head, SC
From $111 a night
- grill/bbq - private
- private pool
- coffee maker
- cookware
Location not published
Book direct on Hilton Head Island Vacations
34 West Beach Lagoon
Villa · 4 bed · 5.5 bath · sleeps 11
Hilton Head, SC
From $111 a night
- beach cart
- dogs considered
- grill/bbq - private
- hot tub/spa - private
Location not published
Book direct on Hilton Head Island Vacations
Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat
Villa · 3 bed · 3 bath · sleeps 12
Hilton Head Island, SC
From $125 a night
- shared pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
Summer Hygge
House · 3 bed · sleeps 10
Hilton Head Island, SC
From $125 a night
- air conditioning
- attached garage
- bbq grill
- balcony
Exact location
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Scenic Deck and Access to Community Pool - Tranquil Villa Haven
Villa · 3 bed · 3 bath · sleeps 8
Hilton Head Island, SC
From $132 a night
- shared pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
Luxurious Oceanfront Haven with Huge Pool and Entertainment Area - Exquisite Retreat
House · 6 bed · 7 bath · sleeps 24
Hilton Head Island, SC
From $180 a night
- private pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
Ocean and Marsh View Home with private pool, dog friendly, beachfront
House · 6 bed · 6.5 bath · sleeps 16
Hilton Head Island, SC
From $180 a night
- private pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
Evian 240
Villa · 3 bed · 3 bath · sleeps 8
Hilton Head Island, SC
From $210 a night
- resort
- clean with disinfectant
- non smoking only
- queen-2
City-level location
Book direct on Hilton Head Vacation Rentals
South Beach Lane 47
House · 2 bed · sleeps 8
Hilton Head Island, SC
From $210 a night
- resort
- clean with disinfectant
- non smoking only
- telephone
City-level location
Book direct on Hilton Head Vacation Rentals
10 Brigantine
Villa · 7 bed · 7 bath · sleeps 18
Hilton Head, SC
From $225 a night
- beach cart
- grill/bbq - private
- hot tub/spa - private
- pool access
Location not published
Book direct on Hilton Head Island Vacations
5 Juniper Lane
Villa · 5 bed · 4 bath · sleeps 16
Hilton Head, SC
From $225 a night
- beach cart
- dogs considered
- grill/bbq - private
- hot tub/spa - private
Location not published
Book direct on Hilton Head Island Vacations
Willow Oak 2
House · 3 bed · 3.5 bath · sleeps 9
Hilton Head Island, SC
From $285 a night
- resort
- clean with disinfectant
- non smoking only
- telephone
City-level location
Book direct on Hilton Head Vacation Rentals
Schooner Court 704
Villa · 4 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $296 a night
- resort
- clean with disinfectant
- queen-2
- non smoking only
City-level location
Book direct on Hilton Head Vacation Rentals
Bittern 15
House · 3 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $304 a night
- clean with disinfectant
- queen-2
- non smoking only
- telephone
City-level location
Book direct on Hilton Head Vacation Rentals
2268 Heritage Villas: stunning lagoon view, short walk to Harbour Town Golf Links!
Villa · 2 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $419 a night
- air conditioning
- available in the house: free wifi
- barbecue grill
- bathtub or shower
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Tranquil Deer Island treehouse in Sea Pines Resort with beach bikes and chairs
House · 2 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $427 a night
- air conditioning
- available in the house: wifi
- heating
- iron/ironing board
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Serene Lagoon Views; Screened Porch, Patio & Deck; 3 Min. Walk to Harbourtown Restaurants & Shops!
House · 3 bed · 3 bath · sleeps 8
Hilton Head Island, SC
From $535 a night
- air conditioning
- balcony
- barbecue grill
- bedsheets provided
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Surf Scoter 12
House · 4 bed · 4 bath · sleeps 12
Hilton Head Island, SC
From $566 a night
- resort
- clean with disinfectant
- non smoking only
- telephone
City-level location
Book direct on Hilton Head Vacation Rentals
Collier Beach 16
House · 5 bed · 2 bath · sleeps 12
Hilton Head Island, SC
From $754 a night
- clean with disinfectant
- non smoking only
- beachfront
- telephone
City-level location
Book direct on Hilton Head Vacation Rentals
Sandpiper 21
House · 6 bed · 6.5 bath · sleeps 12
Hilton Head Island, SC
From $1,704 a night
- clean with disinfectant
- non smoking only
- telephone
- area fitnesscenter
City-level location
Book direct on Hilton Head Vacation Rentals
Golf, Sea & Sunshine
Villa · 2 bed · 1 bath · sleeps 8
Hilton Head Island, SC
From $89 a night
Exact location
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Serenity at Shelter Cove
Villa · 2 bed · 1 bath · sleeps 8
Hilton Head Island, SC
From $100 a night
Exact location
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Water Oak Villa
Villa · 3 bed · 1 bath · sleeps 12
Hilton Head Island, SC
From $105 a night
Exact location
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Beach Runners
House · 3 bed · 1 bath · sleeps 8
Hilton Head Island, SC
From $106 a night
Exact location
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Marriott’s SurfWatch
Villa · 2 bed · 2 bath · sleeps 8
Hilton Head, SC
From $129 a night
- air conditioning
- alarm clock
- all doors have lever handles
- audible fire alarm
Location not published
Book direct on Marriott vacation club rentals from owners
Ocean Breeze*
House · 2 bed · 1 bath · sleeps 8
Hilton Head Island, SC
From $129 a night
Exact location
Book direct on iTrip
Marriott’s Barony Beach Club
Villa · 2 bed · 2 bath · sleeps 8
Hilton Head, SC
From $155 a night
- air conditioning
- alarm clock
- all doors have lever handles
- audible fire alarm
Location not published
Book direct on Marriott vacation club rentals from owners
Come Sail Away
House · 3 bed · 1 bath · sleeps 8
Hilton Head Island, SC
From $158 a night
Exact location
Book direct on iTrip
Sailors Cove
House · 4 bed · 1 bath · sleeps 11
Hilton Head Island, SC
From $158 a night
Exact location
Book direct on iTrip
Another Day In Paradise
House · 4 bed · 1 bath · sleeps 11
Hilton Head Island, SC
From $172 a night
Exact location
Book direct on iTrip
Luxe Coastal Beach Villa - King Bed
Villa · 2 bed · 2 bath · sleeps 8
Hilton Head Island
From $175 a night
Exact location
Book direct on Shades of Blue Short Term Rentals
Harbour Town Haven
Townhome · 4 bed · 1 bath · sleeps 10
Hilton Head Island, SC
From $176 a night
Exact location
Book direct on iTrip
Spacious dog-friendly villa, walk to the beach
House · 3 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $177 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
3506 Windsor Court S. - Updated Penthouse Oceanfront Villa - Enjoy Ocean Breezes on the Balcony!
Villa · 2 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $190 a night
City-level location
Book direct on Savvy
Siesta by the Sea
Villa · 3 bed · 1 bath · sleeps 9
Hilton Head Island, SC
From $203 a night
Exact location
Book direct on iTrip
2 BR Beachwalk condo in Shipyard-steps to the beach and across from the Sonesta Resort
Condo · 2 bed · 2 bath · sleeps 8
Hilton Head Island, SC
From $207 a night
Exact location
Book direct on CielStay
Marriott’s Grande Ocean
Villa · 2 bed · 2 bath · sleeps 8
Hilton Head, SC
From $207 a night
- air conditioning
- alarm clock
- all doors have lever handles
- audible fire alarm
Location not published
Book direct on Marriott vacation club rentals from owners
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-31 08:42 UTC. Prices and facts are whatever the manager published on their own site.