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Holiday Rentals in Hilton Head

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767 rentals in Hilton Head.
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Luxury Home w/ Private Pool, AMAZING VIEWS & Pool Table! Ask about 15-25% OFF, holiday rental in Hilton Head

Luxury Home w/ Private Pool, AMAZING VIEWS & Pool Table! Ask about 15-25% OFF

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Stop Here! Can’t Beat This Villamare Top Floor Vacation Spot, holiday rental in Hilton Head

Stop Here! Can’t Beat This Villamare Top Floor Vacation Spot

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3406 Resort Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, Fitness, holiday rental in Hilton Head

3406 Resort Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, Fitness

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palmetto Dunes Ranch-Lagoon View, Short Walk to Beach, holiday rental in Hilton Head

Palmetto Dunes Ranch-Lagoon View, Short Walk to Beach

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2br/2 Ba Island Club Resort, 150 Yards From The Best Beach On Hilton Head Island, holiday rental in Hilton Head

2br/2 Ba Island Club Resort, 150 Yards From The Best Beach On Hilton Head Island

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Crest 2509 - Oceanview 5th Floor Condo - Refurbished Spring 2021, holiday rental in Hilton Head

Sea Crest 2509 - Oceanview 5th Floor Condo - Refurbished Spring 2021

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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2306 Ocean View Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, etc, holiday rental in Hilton Head

2306 Ocean View Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, etc

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Breakers Oceanfront Villa with Beautiful View of Ocean & Pool, holiday rental in Hilton Head

Breakers Oceanfront Villa with Beautiful View of Ocean & Pool

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pet Friendly With Walk to Beach! Private, Quiet Retreat! Access to Pool, holiday rental in Hilton Head

Pet Friendly With Walk to Beach! Private, Quiet Retreat! Access to Pool

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious, Open & Airy - Private Pool & Spa, 1 minute to beach.  Great for Multip, holiday rental in Hilton Head

Spacious, Open & Airy - Private Pool & Spa, 1 minute to beach. Great for Multip

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Resort Condo - Beach, 3 Pools, Tennis, Restaurants, Fitness, Hot Tub, Sauna!!, holiday rental in Hilton Head

Resort Condo - Beach, 3 Pools, Tennis, Restaurants, Fitness, Hot Tub, Sauna!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Near Ocean Home, Fenced in backyard, Pet Friendly! Ask how to save 15-25%!!, holiday rental in Hilton Head

Near Ocean Home, Fenced in backyard, Pet Friendly! Ask how to save 15-25%!!

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful HarbourSide Villa, Free Bikes, Pool, Beach Shuttle, holiday rental in Hilton Head

Beautiful HarbourSide Villa, Free Bikes, Pool, Beach Shuttle

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ocean One 111  - 3 Bedroom Direct Ocean Front Condo, holiday rental in Hilton Head

Ocean One 111 - 3 Bedroom Direct Ocean Front Condo

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ocean Villa on Hilton Head Island, SC - Steps from the beach and pool., holiday rental in Hilton Head

Ocean Villa on Hilton Head Island, SC - Steps from the beach and pool.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean One 422 - Beachside 4th Floor Condo, holiday rental in Hilton Head

Ocean One 422 - Beachside 4th Floor Condo

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Moss Creek Marsh Cottage With Spectacular Views, holiday rental in Hilton Head

Renovated Moss Creek Marsh Cottage With Spectacular Views

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Courtside 117 - Forest Beach Townhouse Recently Updated, holiday rental in Hilton Head

Courtside 117 - Forest Beach Townhouse Recently Updated

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachwalk 174 - Shipyard Townhouse, holiday rental in Hilton Head

Beachwalk 174 - Shipyard Townhouse

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Courtside 97 - 1st Floor Flat - Wonderful Ground Floor Flat, holiday rental in Hilton Head

Courtside 97 - 1st Floor Flat - Wonderful Ground Floor Flat

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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It's Never Too Early To Think Spring!  Book now!, holiday rental in Hilton Head

It's Never Too Early To Think Spring! Book now!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Best Beaches on HHI & Ocean views from this 1BR villa on South Forest Beach!, holiday rental in Hilton Head

Best Beaches on HHI & Ocean views from this 1BR villa on South Forest Beach!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Top Floor Ocean View, Year Round 84* Heated Pool, Walk to EVERYTHING!, holiday rental in Hilton Head

Top Floor Ocean View, Year Round 84* Heated Pool, Walk to EVERYTHING!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious 2 BR condo w/ Free Tennis! Palmetto Dunes, holiday rental in Hilton Head

Spacious 2 BR condo w/ Free Tennis! Palmetto Dunes

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Springwood 44 - 2 bedroom Townhouse, holiday rental in Hilton Head

Springwood 44 - 2 bedroom Townhouse

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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14 Heron Street - 6 Bedroom Home Close to Beach, holiday rental in Hilton Head

14 Heron Street - 6 Bedroom Home Close to Beach

6 bedrooms
6 bathrooms
Sleeps 19
Match: Sleeps
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Just Listed! Light And Bright Condo W/Balcony In Hilton Head Oceanfront Resort, holiday rental in Hilton Head

Just Listed! Light And Bright Condo W/Balcony In Hilton Head Oceanfront Resort

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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South Forest Beach Villa, Short Walk to Beach, holiday rental in Hilton Head

South Forest Beach Villa, Short Walk to Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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17 Heron Street - 200 Feet to the Beach!, holiday rental in Hilton Head

17 Heron Street - 200 Feet to the Beach!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Courtside 115 - Forest Beach 1st Floor Flat- Updated!, holiday rental in Hilton Head

Courtside 115 - Forest Beach 1st Floor Flat- Updated!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Seaside 140, holiday rental in Hilton Head

Seaside 140

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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40 Ocean Breeze, Beautiful Updated Pet Friendly, Free Bikes, Tennis & Pool, holiday rental in Hilton Head

40 Ocean Breeze, Beautiful Updated Pet Friendly, Free Bikes, Tennis & Pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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67 Plantation Dr - 6 Bedroom home on Harbor Town Golf Links, holiday rental in Hilton Head

67 Plantation Dr - 6 Bedroom home on Harbor Town Golf Links

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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43 Dune Lane - 7 Bedroom, 2nd Row Home, holiday rental in Hilton Head

43 Dune Lane - 7 Bedroom, 2nd Row Home

7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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9 Hunt Club Dr, holiday rental in Hilton Head

9 Hunt Club Dr

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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23 Dune - Mimi's Place - Private Beach Access, Large Pool, Giant Pool Deck, holiday rental in Hilton Head

23 Dune - Mimi's Place - Private Beach Access, Large Pool, Giant Pool Deck

7 bedrooms
7 bathrooms
Sleeps 19
Match: Sleeps
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Private acre estate with Pickle ball court near beach, holiday rental in Hilton Head

Private acre estate with Pickle ball court near beach

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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2 bed/2 bath Hilton Head Resort Ocean Villa-Best Location in Hilton Head Resort, holiday rental in Hilton Head

2 bed/2 bath Hilton Head Resort Ocean Villa-Best Location in Hilton Head Resort

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spectacular Home with Brand New Pool in Harbour Town! Rare December cancellation, holiday rental in Hilton Head

Spectacular Home with Brand New Pool in Harbour Town! Rare December cancellation

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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2 Min Walk 2 Beach, Golf, Tennis, Pickleball, Pvt Heated Pool, SPA, Bikes, Kayak, holiday rental in Hilton Head

2 Min Walk 2 Beach, Golf, Tennis, Pickleball, Pvt Heated Pool, SPA, Bikes, Kayak

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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5 Star Ratings - Ocean View - South Beach Marina, holiday rental in Hilton Head

5 Star Ratings - Ocean View - South Beach Marina

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury at the Beach! Beach, Pool, Tennis, Pickeleball, Restaurants, Beach Bar!, holiday rental in Hilton Head

Luxury at the Beach! Beach, Pool, Tennis, Pickeleball, Restaurants, Beach Bar!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stylishly Renovated Villa With Fabulous Views and All Amenities, holiday rental in Hilton Head

Stylishly Renovated Villa With Fabulous Views and All Amenities

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beaches are open! Private Pool, beach access, backyard, Bikes, pet friendly, holiday rental in Hilton Head

Beaches are open! Private Pool, beach access, backyard, Bikes, pet friendly

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Charming 3 Br Home, Private Pool And Dock On Serene Lagoon In Palmetto Dunes., holiday rental in Hilton Head

Charming 3 Br Home, Private Pool And Dock On Serene Lagoon In Palmetto Dunes.

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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3rd Row On Beach Path...Steps to Ocean! Major Renovations Just Completed!, holiday rental in Hilton Head

3rd Row On Beach Path...Steps to Ocean! Major Renovations Just Completed!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Oceanfront Resort - Ocean View - Beach Villa A329, holiday rental in Hilton Head

Oceanfront Resort - Ocean View - Beach Villa A329

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Panoramic Direct Oceanfront View in Admirals Row, holiday rental in Hilton Head

Panoramic Direct Oceanfront View in Admirals Row

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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3 BR w/Direct Ocean Front View; Don't Wait!  Only 2 Spring/Summer Weeks Left!, holiday rental in Hilton Head

3 BR w/Direct Ocean Front View; Don't Wait! Only 2 Spring/Summer Weeks Left!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Redecorated Villamare 2517, holiday rental in Hilton Head

Beautifully Redecorated Villamare 2517

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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