Stays for 16+ guests in Hilton Head Island, SC
Stays for 16+ guests in Hilton Head Island, SC, from $180 a night. Book direct on each manager's site, no OTA fee.
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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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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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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
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
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
1A Sea Lane - 4th Row Exceptional Family Home with Private Pool & Spa!
House · 6 bed · 7.5 bath · sleeps 20
Hilton Head Island, SC
From $550 a night
City-level location
Book direct on Savvy
Hilton Head 5BR Retreat Steps from Beach & Golf
House · 5 bed · 4 bath · sleeps 16
Island
From $716 a night
Exact location
Book direct on gibbonsgp.com
22 Dove Street - Fantastic Updated 2nd Row Home with Ocean Views!
House · 6 bed · 5.5 bath · sleeps 17
Hilton Head Island, SC
From $750 a night
City-level location
Book direct on Savvy
94 Mooring Buoy - AMAZING NEW Beach Home - No Detail Missed!
House · 6 bed · 6.5 bath · sleeps 24
Hilton Head Island, SC
From $850 a night
City-level location
Book direct on Savvy
Private Pool and Spa Oasis - Spacious Family Retreat with Entertainment
Loft · 5 bed · sleeps 22
Hilton Head Island, SC
From $391 a night
- private pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
Oceanfront Home with Private Pool and Hot Tub - Stunning Coastal Retreat
House · 5 bed · sleeps 16
Hilton Head Island, SC
From $1,379 a night
- private pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
Heated Pool and Spa with Private Beach Access - Stunning Oceanfront Escape
House · 8 bed · sleeps 19
Hilton Head Island, SC
From $1,415 a night
- private pool
- sleeps
- waterfront
City-level location
Book direct on Sleep By The Beach, Curated American Coastal Rentals
**.08 Miles To Beach **Oceanside, Sea Pines, Hilton Head 4th Row From Beach
sleeps 16
Tybee Island
From $1,105 a night
- air conditioning
- bar
- dryer
- elevator
Exact location
Book direct on Niranar
7 Singleton Beach Place
Villa · 7 bed · 7.5 bath · sleeps 20
Hilton Head Island, SC
No nightly rate published
- elevator
- heated pool
- private pool
- air conditioning
Exact location
Book direct on Hilton Head Vacation Rentals
Bridger's Cache Ski Lodge
Lodge · 5 bed · 5 bath · sleeps 18
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- foosball table
- heated garage
- hotel-style bedding
Exact location
Book direct on Winter Park CO Lodging
Casa de Montana
Farmhouse · 7 bed · 7 bath · sleeps 19
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- bike storage
- booster seat
- boot & glove dryer
Exact location
Book direct on Winter Park CO Lodging
Corridor Way Chalet
Chalet · 5 bed · 4 bath · sleeps 16
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- boot & glove dryer
- heated floors
- heated garage
Exact location
Book direct on Winter Park CO Lodging
Creekside Retreat
Townhome · 5 bed · 4 bath · sleeps 18
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- heated floors
- heated garage
- high speed wi-fi
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
Dilly Dally Chalet
Chalet · 5 bed · 3 bath · sleeps 17
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- electric fireplace
- heated garage
- high chair
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
Eagle Wind Lodge
Lodge · 5 bed · 4 bath · sleeps 16
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- ev charger
- hotel-style bedding
- jetted bathtub
Exact location
Book direct on Winter Park CO Lodging
Elk Lodge
Lodge · 5 bed · 5 bath · sleeps 19
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- heated garage
- high chair
- hotel-style bedding
Exact location
Book direct on Winter Park CO Lodging
Fore Seasons Lodge
Lodge · 7 bed · 7 bath · sleeps 16
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- booster seat
- heated floors
- heated garage
Exact location
Book direct on Winter Park CO Lodging
Jane's Ski Chalet
Chalet · 5 bed · 4 bath · sleeps 17
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- heated floors
- heated garage
- high chair
Exact location
Book direct on Winter Park CO Lodging
Lakota Cedarcrest
Lodge · 8 bed · 8.5 bath · sleeps 19
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- bike storage
- heated floors
- heated garage
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
Lakota Lookout
Townhome · 4 bed · 4.5 bath · sleeps 16
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- bike storage
- boot & glove dryer
- high chair
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
Lakota Reserve
Townhome · 6 bed · 6 bath · sleeps 18
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- booster seat
- dog friendly (one dog maximum)
- ev charger
Exact location
Book direct on Winter Park CO Lodging
Lookout 3
Villa · 7 bed · 6.5 bath · sleeps 23
Hilton Head, SC
No nightly rate published
- pool heat
- private pool
- private spa
- spa heat
Exact location
Book direct on Hilton Head Vacation Rentals
Slopeside Retreat
Townhome · 4 bed · 3 bath · sleeps 17
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- heated garage
- hotel-style bedding
- kids pick
Exact location
Book direct on Winter Park CO Lodging
Trout Creek Lodge
Lodge · 6 bed · 7 bath · sleeps 19
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- air hockey table
- booster seat
- foosball table
Exact location
Book direct on Winter Park CO Lodging
Two Brothers Lodge
Lodge · 6 bed · 4 bath · sleeps 19
Hilton Head, SC
No nightly rate published
- 4wd recommended in winter
- heated garage
- high chair
- hotel-style bedding
Exact location
Book direct on Winter Park CO Lodging
1 Buck Island
Villa · 8 bed · 9.5 bath · sleeps 26
No nightly rate published
- heated pool
- hot tub
- private pool
- pets considered
Approximate area
Book direct on Hilton Head Vacation Rentals
10 Junket
Villa · 8 bed · 10 bath · sleeps 24
No nightly rate published
- ping pong table
- heated pool
- hot tub
- private pool
Approximate area
Book direct on Hilton Head Vacation Rentals
105 Mooring Buoy
Villa · 6 bed · 6.5 bath · sleeps 16
No nightly rate published
- heated pool
- hot tub
- private pool
- pets considered
Approximate area
Book direct on Hilton Head Vacation Rentals
11 Cat Boat
Villa · 6 bed · 6.5 bath · sleeps 18
No nightly rate published
- heated pool
- hot tub
- private pool
- air conditioning
Approximate area
Book direct on Hilton Head Vacation Rentals
11 High Rigger
Villa · 4 bed · 4.5 bath · sleeps 18
No nightly rate published
- air conditioning
- clothes dryer
- heating
- internet
Approximate area
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11 Iron Clad
Villa · 8 bed · 8.5 bath · sleeps 21
No nightly rate published
- heated pool
- hot tub
- private pool
- air conditioning
Approximate area
Book direct on Hilton Head Vacation Rentals
111 Mooring Buoy
Villa · 8 bed · 8.5 bath · sleeps 26
No nightly rate published
- air conditioning
- clothes dryer
- internet
- iron & board
Approximate area
Book direct on Hilton Head Vacation Rentals
13 Wagon Rd
Villa · 5 bed · 5 bath · sleeps 17
No nightly rate published
- air conditioning
- clothes dryer
- internet
- iron & board
Approximate area
Book direct on Hilton Head Vacation Rentals
170 Mooring Buoy
Villa · 6 bed · 5.5 bath · sleeps 16
No nightly rate published
- foosball
- ping pong table
- heated pool
- private pool
Approximate area
Book direct on Hilton Head Vacation Rentals
19 Avocet
Villa · 6 bed · 5 bath · sleeps 20
No nightly rate published
- air conditioning
- clothes dryer
- internet
- iron & board
Approximate area
Book direct on Hilton Head Vacation Rentals
2 Galleon
Villa · 8 bed · 7 bath · sleeps 24
No nightly rate published
- heated pool
- hot tub
- private pool
- air conditioning
Approximate area
Book direct on Hilton Head Vacation Rentals
2 High Rigger
Villa · 7 bed · 8.5 bath · sleeps 16
No nightly rate published
- heated pool
- hot tub
- private pool
- air conditioning
Approximate area
Book direct on Hilton Head Vacation Rentals
2 Sea Lane
Villa · 5 bed · 7 bath · sleeps 16
No nightly rate published
- air conditioning
- clothes dryer
- internet
- iron & board
Approximate area
Book direct on Hilton Head Vacation Rentals
20 Sea Oak Lane
Beach house · 9 bed · 7.5 bath · sleeps 24
No nightly rate published
- air conditioning
- clothes dryer
- internet
- iron & board
Approximate area
Book direct on Hilton Head Vacation Rentals
7 Galleon
Villa · 6 bed · 6.5 bath · sleeps 19
No nightly rate published
- elevator
- heated pool
- hot tub
- private pool
Approximate area
Book direct on Hilton Head Vacation Rentals
8 Armada
Villa · 10 bed · 11 bath · sleeps 24
No nightly rate published
- game room
- elevator
- heated pool
- hot tub
Approximate area
Book direct on Hilton Head Vacation Rentals
8 Iron Clad
Villa · 6 bed · 6.5 bath · sleeps 18
No nightly rate published
- game room
- ping pong table
- hot tub
- private pool
Approximate area
Book direct on Hilton Head Vacation Rentals
99 Mooring Buoy
Villa · 6 bed · 6.5 bath · sleeps 16
No nightly rate published
- heated pool
- hot tub
- private pool
- pets considered
Approximate area
Book direct on Hilton Head Vacation Rentals
Corine Lane 13
Villa · 6 bed · sleeps 19
Hilton Head, SC
No nightly rate published
- blender
- dishwasher
- freezer
- microwave
Exact location
Book direct on Hilton Head Vacation Rentals
Home - 10 Singleton Shore Manor, Singleton Beach
House · 7 bed · 7 bath · sleeps 18
Hilton Head Island
No nightly rate published
- kitchen
- living room
- dining room
- trash bags
Exact location
Book direct on Hilton Head Properties R & R
Home - 16 Mallard, Forest Beach
House · 7 bed · 5 bath · sleeps 22
Hilton Head Island
No nightly rate published
- kitchen
- game room
- living room
- dining room
Exact location
Book direct on Hilton Head Properties R & R
Home - 25 Starboard Tack, Palmetto Dunes
House · 7 bed · 6 bath · sleeps 18
Hilton Head Island
No nightly rate published
- dining room
- living room
- kitchen
- game room
Exact location
Book direct on Hilton Head Properties R & R
10 Bald Eagle
Villa · 6 bath · sleeps 20
Hilton Head, SC
No nightly rate published
- beach cart
- grill/bbq - private
- hot tub/spa - private
- pool access
Exact location
Book direct on Hilton Head Island Vacations
Capri 2
Villa · 7 bed · 7.5 bath · sleeps 22
Hilton Head, SC
No nightly rate published
Exact location
Book direct on Hilton Head Vacation Rentals
Egret 5
Villa · 6 bed · 2 bath · sleeps 18
Hilton Head, SC
No nightly rate published
Exact location
Book direct on Hilton Head Vacation Rentals
Home - 5 Eastwind, Palmetto Dunes
House · 6 bed · 6 bath · sleeps 16
Hilton Head Island
No nightly rate published
- kitchen
- living room
- dining room
- trash bags
Exact location
Book direct on Hilton Head Properties R & R
Homes - Moon River Retreat with Private Dock, Daufuskie
House · 9 bed · 9 bath · sleeps 18
Daufuskie Island
No nightly rate published
- kitchen
- living room
- dining room
- bath soaps
Exact location
Book direct on Hilton Head Properties R & R
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 2026-10-30 10:27 UTC. Prices and facts are whatever the manager published on their own site.