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5+ Bedroom Vacation Rentals

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101 rentals found
Stunning oceanfront home with pool, priv...

Dune Lane 105Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’ve been planning a group hideaway to Hilton Head but haven’t yet found the ideal...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Stunning Oceanfront Hideaway with Privat...
4.7
(27)

HeavenOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation possible!*This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Gorgeous new luxury beach house - be the...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this pretty professionally decorated coastal beach home. As a guest at Serenity Now you are...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Gorgeous oceanfront beach home with priv...

Amazing oceanfront home…..your ideal vacation hideaway! This home is ideal for entertaining with eight bedrooms, eight full baths, 1 half bath and huge living areas with sizable flat screen TV's and calming sitting areas to appreciate the...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Renovated spacious home with private poo...
4.8
(6)

Full Sweep 66Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property has a pool that can be heated between Labor Day and Memorial Day for an additional...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Family-Friendly Home w/Private Pool, Scr...
4.4
(30)

Gloucester 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Spacious Home - Private Pool & Big Deck ...
4.2
(20)

Mooring BuoyOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation possible!*This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
9 Sandy Beach, Close to Beach, Pool, Ele...
4.8
(10)

9 Sandy Beach Trail, Hilton Head Island. Welcome to your bespoke-constructed vacation home! This impressive property features an open-concept layout with the kitchen, living, and dining areas facing the pool, creating a seamless indoor-outdoor...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Spectacular home located on the Robert T...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, huge windows, skylights and amazing vistas make this home one of the most inviting you will...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
14 Collier Beach, Oceanfront, Pool, Elev...
4.7
(18)

14 Collier Beach, Hilton Head Island is a striking oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grille. The home features a opulent master suite with...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
13 Moonshell, Close to Beach, Pool, Big ...
4.6
(31)

13 Moonshell Rd, Hilton Head is a ideal getaway for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and relax. The roomy fenced backyard with a private pool and outdoor bar provides a amazing...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
12 Whelk, Steps to the Beach, Private Po...
4.3
(12)

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this newly remodeled four-story property offers striking ocean...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Large Six Bedroom Custom-Built Home with...

This home is designed to fit your next family vacation! The kitchen comes completely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The enormous kitchen island...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
9 Singleton Beach, Newly Renovated, Ocea...
5.0
(2)

*New Construction Update(Spring 2025): Updated Kitchen, Updated Master Bathrooms, Updated Half Bathroom, (Jack n Jill Bathrooms to be refreshed winter 2025), New Washer and Dryer sets*9 Singleton Beach, Hilton Head Island. This oceanfront gem is a...

  • Hilton Head
  • 7 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
60 Lawton Road, Sea Pines

Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here's the skinny - just buzz us for more details: Our advertised prices are our very best rates and calendar shows real time availability. We encourage you to book online!• Charmingly...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
205 Jacana-\
5.0
(6)

**Luxurious 6-Bedroom Beach Home Just Steps from North Forest Beach!**Escape to your dream vacation in this cavernous and delightfully designed 6-bedroom, 6.5-bath beach home, just a few sandy steps from the gorgeous North Forest Beach. Whether...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
2 Collier Beach, Oceanfront, Dogs OK, Po...
3.8
(10)

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this lavish oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
4 Surfwatch Way, Pet Friendly, Large Poo...
4.6
(77)

4 Surf Watch Way is a excellent 6-bedroom, 5.5-bathroom, pet friendly home accommodating up to 16 guests and making it ideal for family get-togethers or enormous gatherings. Outside, a fantastic deck overlooks the pool and spa, with a completely...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18