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Holiday Rentals with Pools in Hilton Head

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
399 rentals in Hilton Head.
Sun, Surf, Sand! 309 Breakers, Free Bikes Included, holiday rental in Hilton Head
Sun, Surf, Sand! 309 Breakers, Free Bikes Included, holiday rental in Hilton Head
Sun, Surf, Sand! 309 Breakers, Free Bikes Included, holiday rental in Hilton Head

Sun, Surf, Sand! 309 Breakers, Free Bikes Included

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
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The Cottages on Beautiful Shipyard Plantation, holiday rental in Hilton Head
The Cottages on Beautiful Shipyard Plantation, holiday rental in Hilton Head
The Cottages on Beautiful Shipyard Plantation, holiday rental in Hilton Head

The Cottages on Beautiful Shipyard Plantation

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Great Resort - Close to the Beach  Sleeps 6, holiday rental in Hilton Head
Great Resort - Close to the Beach  Sleeps 6, holiday rental in Hilton Head
Great Resort - Close to the Beach  Sleeps 6, holiday rental in Hilton Head

Great Resort - Close to the Beach Sleeps 6

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Deluxe Ocean Dunes Oceanfront Luxury, holiday rental in Hilton Head
Deluxe Ocean Dunes Oceanfront Luxury, holiday rental in Hilton Head
Deluxe Ocean Dunes Oceanfront Luxury, holiday rental in Hilton Head

Deluxe Ocean Dunes Oceanfront Luxury

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Beautifully Appointed and Newly Renovated Ocean-front Villa - Heated Pool, holiday rental in Hilton Head
Beautifully Appointed and Newly Renovated Ocean-front Villa - Heated Pool, holiday rental in Hilton Head
Beautifully Appointed and Newly Renovated Ocean-front Villa - Heated Pool, holiday rental in Hilton Head

Beautifully Appointed and Newly Renovated Ocean-front Villa - Heated Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Hilton Head Island Sea Pines villa with nearest access to beach and golf cbeach, holiday rental in Hilton Head
Hilton Head Island Sea Pines villa with nearest access to beach and golf cbeach, holiday rental in Hilton Head
Hilton Head Island Sea Pines villa with nearest access to beach and golf cbeach, holiday rental in Hilton Head

Hilton Head Island Sea Pines villa with nearest access to beach and golf cbeach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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176 The Greens, holiday rental in Hilton Head
176 The Greens, holiday rental in Hilton Head
176 The Greens, holiday rental in Hilton Head

176 The Greens

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Heart of Coligny Beach~ Panoramic Ocean Views, holiday rental in Hilton Head
Heart of Coligny Beach~ Panoramic Ocean Views, holiday rental in Hilton Head
Heart of Coligny Beach~ Panoramic Ocean Views, holiday rental in Hilton Head

Heart of Coligny Beach~ Panoramic Ocean Views

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Tennis Master 1101 Private and Recently Updated, 5 Minute Walk to the Beach, holiday rental in Hilton Head
Tennis Master 1101 Private and Recently Updated, 5 Minute Walk to the Beach, holiday rental in Hilton Head
Tennis Master 1101 Private and Recently Updated, 5 Minute Walk to the Beach, holiday rental in Hilton Head

Tennis Master 1101 Private and Recently Updated, 5 Minute Walk to the Beach

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Condo on Beachfront Resort, holiday rental in Hilton Head
Condo on Beachfront Resort, holiday rental in Hilton Head
Condo on Beachfront Resort, holiday rental in Hilton Head

Condo on Beachfront Resort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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2 Bedroom 2 Bath Condo For Rent on Hilton Head Island, holiday rental in Hilton Head
2 Bedroom 2 Bath Condo For Rent on Hilton Head Island, holiday rental in Hilton Head
2 Bedroom 2 Bath Condo For Rent on Hilton Head Island, holiday rental in Hilton Head

2 Bedroom 2 Bath Condo For Rent on Hilton Head Island

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Sunshine Bliss Ocean View, holiday rental in Hilton Head
Sunshine Bliss Ocean View, holiday rental in Hilton Head
Sunshine Bliss Ocean View, holiday rental in Hilton Head

Sunshine Bliss Ocean View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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 2 BEDROOM 2 BATH CONDO RENT ON HILTON HEAD ISLAND, holiday rental in Hilton Head
 2 BEDROOM 2 BATH CONDO RENT ON HILTON HEAD ISLAND, holiday rental in Hilton Head
 2 BEDROOM 2 BATH CONDO RENT ON HILTON HEAD ISLAND, holiday rental in Hilton Head

2 BEDROOM 2 BATH CONDO RENT ON HILTON HEAD ISLAND

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Extreme Makeover 2 BR/2BA - Free Wi-Fi. Closest to Pool and Boardwalk to Beach., holiday rental in Hilton Head
Extreme Makeover 2 BR/2BA - Free Wi-Fi. Closest to Pool and Boardwalk to Beach., holiday rental in Hilton Head
Extreme Makeover 2 BR/2BA - Free Wi-Fi. Closest to Pool and Boardwalk to Beach., holiday rental in Hilton Head

Extreme Makeover 2 BR/2BA - Free Wi-Fi. Closest to Pool and Boardwalk to Beach.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
53 Springwood Villas - 2 bedroom/2.5 townhome, community pool, tennis, holiday rental in Hilton Head
53 Springwood Villas - 2 bedroom/2.5 townhome, community pool, tennis, holiday rental in Hilton Head
53 Springwood Villas - 2 bedroom/2.5 townhome, community pool, tennis, holiday rental in Hilton Head

53 Springwood Villas - 2 bedroom/2.5 townhome, community pool, tennis

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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306 Barrington Arms -Oceanfront Luxury Villa, holiday rental in Hilton Head
306 Barrington Arms -Oceanfront Luxury Villa, holiday rental in Hilton Head
306 Barrington Arms -Oceanfront Luxury Villa, holiday rental in Hilton Head

306 Barrington Arms -Oceanfront Luxury Villa

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
Welcome Beach Lovers! South Forest Beach | 2 Blocks To Beach | Near Coligny Park, holiday rental in Hilton Head
Welcome Beach Lovers! South Forest Beach | 2 Blocks To Beach | Near Coligny Park, holiday rental in Hilton Head
Welcome Beach Lovers! South Forest Beach | 2 Blocks To Beach | Near Coligny Park, holiday rental in Hilton Head

Welcome Beach Lovers! South Forest Beach | 2 Blocks To Beach | Near Coligny Park

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Remodeled Villa on Golf Course Close to Beach, holiday rental in Hilton Head
Remodeled Villa on Golf Course Close to Beach, holiday rental in Hilton Head
Remodeled Villa on Golf Course Close to Beach, holiday rental in Hilton Head

Remodeled Villa on Golf Course Close to Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Hilton Head Island SC North Shore Place 2 Bed 2 Bath Villa , holiday rental in Hilton Head
Hilton Head Island SC North Shore Place 2 Bed 2 Bath Villa , holiday rental in Hilton Head
Hilton Head Island SC North Shore Place 2 Bed 2 Bath Villa , holiday rental in Hilton Head

Hilton Head Island SC North Shore Place 2 Bed 2 Bath Villa

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Changes in Latitude/walk to BEACH and Coligny, holiday rental in Hilton Head
Changes in Latitude/walk to BEACH and Coligny, holiday rental in Hilton Head
Changes in Latitude/walk to BEACH and Coligny, holiday rental in Hilton Head

Changes in Latitude/walk to BEACH and Coligny

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Desirable Seacrest Oceanfront, holiday rental in Hilton Head
Desirable Seacrest Oceanfront, holiday rental in Hilton Head
Desirable Seacrest Oceanfront, holiday rental in Hilton Head

Desirable Seacrest Oceanfront

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa, holiday rental in Hilton Head
328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa, holiday rental in Hilton Head
328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa, holiday rental in Hilton Head

328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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3 Night Heron Lakeside - Rare Lakeside home on Hilton Head, holiday rental in Hilton Head
3 Night Heron Lakeside - Rare Lakeside home on Hilton Head, holiday rental in Hilton Head
3 Night Heron Lakeside - Rare Lakeside home on Hilton Head, holiday rental in Hilton Head

3 Night Heron Lakeside - Rare Lakeside home on Hilton Head

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Premium Finishes and Amenities, holiday rental in Hilton Head
Premium Finishes and Amenities, holiday rental in Hilton Head
Premium Finishes and Amenities, holiday rental in Hilton Head

Premium Finishes and Amenities

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Beach, Tennis, Golf Resort, Hilton Head , holiday rental in Hilton Head
Beach, Tennis, Golf Resort, Hilton Head , holiday rental in Hilton Head
Beach, Tennis, Golf Resort, Hilton Head , holiday rental in Hilton Head

Beach, Tennis, Golf Resort, Hilton Head

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
Seaside 140, holiday rental in Hilton Head
Seaside 140, holiday rental in Hilton Head
Seaside 140, holiday rental in Hilton Head

Seaside 140

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Check-out
Payment Protection
North Shore Place Unit 405, holiday rental in Hilton Head
North Shore Place Unit 405, holiday rental in Hilton Head
North Shore Place Unit 405, holiday rental in Hilton Head

North Shore Place Unit 405

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Breakers 139 - Remodeled Ocean Front Condo!, holiday rental in Hilton Head
Breakers 139 - Remodeled Ocean Front Condo!, holiday rental in Hilton Head
Breakers 139 - Remodeled Ocean Front Condo!, holiday rental in Hilton Head

Breakers 139 - Remodeled Ocean Front Condo!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Direct Oceanfront Views, 339 Breakers. Sleeps 4, holiday rental in Hilton Head
Direct Oceanfront Views, 339 Breakers. Sleeps 4, holiday rental in Hilton Head
Direct Oceanfront Views, 339 Breakers. Sleeps 4, holiday rental in Hilton Head

Direct Oceanfront Views, 339 Breakers. Sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Steps away from the BEACH!!!, holiday rental in Hilton Head
Steps away from the BEACH!!!, holiday rental in Hilton Head
Steps away from the BEACH!!!, holiday rental in Hilton Head

Steps away from the BEACH!!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Completely Updated  - Comfortable, Casual and Clean - on site pool - walk to the, holiday rental in Hilton Head
Completely Updated  - Comfortable, Casual and Clean - on site pool - walk to the, holiday rental in Hilton Head
Completely Updated  - Comfortable, Casual and Clean - on site pool - walk to the, holiday rental in Hilton Head

Completely Updated - Comfortable, Casual and Clean - on site pool - walk to the

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Payment Protection
Beautifully Decorated, Cozy, Warm And Inviting 1st Floor Retreat!, holiday rental in Hilton Head
Beautifully Decorated, Cozy, Warm And Inviting 1st Floor Retreat!, holiday rental in Hilton Head
Beautifully Decorated, Cozy, Warm And Inviting 1st Floor Retreat!, holiday rental in Hilton Head

Beautifully Decorated, Cozy, Warm And Inviting 1st Floor Retreat!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
2BR Beach Escape and Condo at Hilton Head , holiday rental in Hilton Head
2BR Beach Escape and Condo at Hilton Head , holiday rental in Hilton Head
2BR Beach Escape and Condo at Hilton Head , holiday rental in Hilton Head

2BR Beach Escape and Condo at Hilton Head

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Newly Updated Breakers Villa. Sleeps 4, Beachfront, Pool, holiday rental in Hilton Head
Newly Updated Breakers Villa. Sleeps 4, Beachfront, Pool, holiday rental in Hilton Head
Newly Updated Breakers Villa. Sleeps 4, Beachfront, Pool, holiday rental in Hilton Head

Newly Updated Breakers Villa. Sleeps 4, Beachfront, Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Newly Renovated! Book Now for Prime-Time 2016, holiday rental in Hilton Head
Newly Renovated! Book Now for Prime-Time 2016, holiday rental in Hilton Head
Newly Renovated! Book Now for Prime-Time 2016, holiday rental in Hilton Head

Newly Renovated! Book Now for Prime-Time 2016

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
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Payment Protection
Beachfront Paradise, 336 Breakers. Sleeps 4-6, Free Bikes, holiday rental in Hilton Head
Beachfront Paradise, 336 Breakers. Sleeps 4-6, Free Bikes, holiday rental in Hilton Head
Beachfront Paradise, 336 Breakers. Sleeps 4-6, Free Bikes, holiday rental in Hilton Head

Beachfront Paradise, 336 Breakers. Sleeps 4-6, Free Bikes

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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490 Captain's Cove, 3 Bedroom PD Townhouse, 10/1/2022 Completed Renovation, holiday rental in Hilton Head
490 Captain's Cove, 3 Bedroom PD Townhouse, 10/1/2022 Completed Renovation, holiday rental in Hilton Head
490 Captain's Cove, 3 Bedroom PD Townhouse, 10/1/2022 Completed Renovation, holiday rental in Hilton Head

490 Captain's Cove, 3 Bedroom PD Townhouse, 10/1/2022 Completed Renovation

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, All pools
More info
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Airy Couples Getaway with Fantastic Golf Views, holiday rental in Hilton Head
Airy Couples Getaway with Fantastic Golf Views, holiday rental in Hilton Head
Airy Couples Getaway with Fantastic Golf Views, holiday rental in Hilton Head

Airy Couples Getaway with Fantastic Golf Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
331 Breakers, Fully Remodeled! Beautiful Oceanfront, Pool, Beach Free Bikes, holiday rental in Hilton Head
331 Breakers, Fully Remodeled! Beautiful Oceanfront, Pool, Beach Free Bikes, holiday rental in Hilton Head
331 Breakers, Fully Remodeled! Beautiful Oceanfront, Pool, Beach Free Bikes, holiday rental in Hilton Head

331 Breakers, Fully Remodeled! Beautiful Oceanfront, Pool, Beach Free Bikes

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Breakers 110 - 1st Floor Ocean Front Condo, holiday rental in Hilton Head
Breakers 110 - 1st Floor Ocean Front Condo, holiday rental in Hilton Head
Breakers 110 - 1st Floor Ocean Front Condo, holiday rental in Hilton Head

Breakers 110 - 1st Floor Ocean Front Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Fabulously Renovated Townhome-Style End Unit w/ Community Saltwater Pool & Golf, holiday rental in Hilton Head
Fabulously Renovated Townhome-Style End Unit w/ Community Saltwater Pool & Golf, holiday rental in Hilton Head
Fabulously Renovated Townhome-Style End Unit w/ Community Saltwater Pool & Golf, holiday rental in Hilton Head

Fabulously Renovated Townhome-Style End Unit w/ Community Saltwater Pool & Golf

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Direct Oceanfront Villa, overlooking  Beautiful Pool and Beach ., holiday rental in Hilton Head
Direct Oceanfront Villa, overlooking  Beautiful Pool and Beach ., holiday rental in Hilton Head
Direct Oceanfront Villa, overlooking  Beautiful Pool and Beach ., holiday rental in Hilton Head

Direct Oceanfront Villa, overlooking Beautiful Pool and Beach .

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
22 Ocean Club - 2 Bedroom Oceanfront Condo, courtyard view!, holiday rental in Hilton Head
22 Ocean Club - 2 Bedroom Oceanfront Condo, courtyard view!, holiday rental in Hilton Head
22 Ocean Club - 2 Bedroom Oceanfront Condo, courtyard view!, holiday rental in Hilton Head

22 Ocean Club - 2 Bedroom Oceanfront Condo, courtyard view!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Ocean Views, Steps to the Beach & Pool, holiday rental in Hilton Head
Ocean Views, Steps to the Beach & Pool, holiday rental in Hilton Head
Ocean Views, Steps to the Beach & Pool, holiday rental in Hilton Head

Ocean Views, Steps to the Beach & Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
Seascape Condo. Steps to the Beach and Pool, holiday rental in Hilton Head
Seascape Condo. Steps to the Beach and Pool, holiday rental in Hilton Head
Seascape Condo. Steps to the Beach and Pool, holiday rental in Hilton Head

Seascape Condo. Steps to the Beach and Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
688 Queens Grant, Short Walk to the Beach, holiday rental in Hilton Head
688 Queens Grant, Short Walk to the Beach, holiday rental in Hilton Head
688 Queens Grant, Short Walk to the Beach, holiday rental in Hilton Head

688 Queens Grant, Short Walk to the Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Community Pool & Tennis Courts; Ground Floor Villa w/ Wooded Lagoon View; Easy H, holiday rental in Hilton Head
Community Pool & Tennis Courts; Ground Floor Villa w/ Wooded Lagoon View; Easy H, holiday rental in Hilton Head
Community Pool & Tennis Courts; Ground Floor Villa w/ Wooded Lagoon View; Easy H, holiday rental in Hilton Head

Community Pool & Tennis Courts; Ground Floor Villa w/ Wooded Lagoon View; Easy H

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Ocean Views; Community Pool, Hot Tub, Grilling Area & Boardwalk to Beach; All Ro, holiday rental in Hilton Head
Ocean Views; Community Pool, Hot Tub, Grilling Area & Boardwalk to Beach; All Ro, holiday rental in Hilton Head
Ocean Views; Community Pool, Hot Tub, Grilling Area & Boardwalk to Beach; All Ro, holiday rental in Hilton Head

Ocean Views; Community Pool, Hot Tub, Grilling Area & Boardwalk to Beach; All Ro

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
Shipyard 3BD Southwind II,  one week available 7/13/24 to 7/20/24, holiday rental in Hilton Head
Shipyard 3BD Southwind II,  one week available 7/13/24 to 7/20/24, holiday rental in Hilton Head
Shipyard 3BD Southwind II,  one week available 7/13/24 to 7/20/24, holiday rental in Hilton Head

Shipyard 3BD Southwind II, one week available 7/13/24 to 7/20/24

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Payment Protection
6 Beach Arbor 1st Floor End Unit. Walk to the Beach, Poolside, Pet Friendly, holiday rental in Hilton Head
6 Beach Arbor 1st Floor End Unit. Walk to the Beach, Poolside, Pet Friendly, holiday rental in Hilton Head
6 Beach Arbor 1st Floor End Unit. Walk to the Beach, Poolside, Pet Friendly, holiday rental in Hilton Head

6 Beach Arbor 1st Floor End Unit. Walk to the Beach, Poolside, Pet Friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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