Vacation Rentals & Villas in Guana Bay

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260 Houses

THE CLIFF

Cupecoy Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 minutes

Match: Garden

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Price per night from

$344

VistaRoyale - Private pool and breathtaking view

Philipsburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing view !!” This is our tenth year staying at VistaRoyale and we don't want to go anywhere else. It has to be one of the most spectacular views on the planet. Every morning you wake up to arriving cruise ships, beautiful rainbows after a morning shower, the brilliant color of the waters in the bay. And your own private infinity pool, veranda and palm tree. New cabinets, appliances and countertop this year really upgraded the kitchen. It is a perfect property to get away, relax, and unwind. The new owners are easy to deal with and very accessible. Can't wait to return!

Responds fast! avg. 1 hour 18 minutes

Match: Garden

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Price per night from

$258

MADRAS... Affordable 5 BR, Short walk to Plum Bay beach, Pool, Views, Full AC!

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$572

Studio de la Baie Nettle

Baie Nettle apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$114

LA SALAMANDRE... Fabulous Waterfront Villa, Private Beach, Heated Pool!

Terres Basses house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Garden

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Price per night from

$1,800

AMBIANCE... Fabulous villa!! 4 Huge equal bedrooms, the PERFECT couples villa!

Terres Basses house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$1,143

Joie de Vivre

Grand Case, French St. Martin villa

  • 3 bedrooms
  • 11 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$1,598

LA HACIENDA...Fabulous 3+1BR villa rental perfect for families

Terres Basses house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$743

OCEANE... Spacious 4BR Villa, Walk to Plum Bay Beach, Heated Pool!

Terres Basses house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$965

VILLA SILOVE... Oh so charming, affordable, and 2 min walk to Orient Beach!

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$258

MES AMIS...Spectacular Ultra Deluxe cliffside masterpiece! Breathtaking views! A

Terres Basses villa

  • 14 bedrooms
  • 13 bathrooms
  • sleeps 26

Match: Garden

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Price per night from

$5,000

Villa MOJITO, charming 2 bedrooms, steps from the beach, private pool

Orient Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Garden

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Price per night from

$309

Tranquil Settings, Porto Cupecoy (1 Bedroom)

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

“Our 3rd anniversary” My husband and I had the pleasure of celebrating our 3rd wedding anniversary at Tranquil Settings! Absolutely loved this place and glad we spent it nestled in Port Cupecoy! Beautiful decor in every room, loved all aspects of Tranquil Settings! The cleanliness and comfort of each room was remarkable! The location is perfect, relaxed on the patio lounge chairs at night enjoying the wonderful view, the pool is just a short walk away, and enjoyed going to the plaza as well. Looking forward to visiting Tranquil Settings again - definitely my #1 choice for our 4th anniversary!!

Match: Garden

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Price per night from

$286

Match: Garden

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Price per night from

$914

ENCORE... Fabulous villa with 6 huge master suites, heated pool

Terres Basses house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Garden

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Price per night from

$1,264

BLUE SAILING.... Sweet affordable villa in Happy Bay. Endless Blue Views!

La Savane house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$485

SEACHEST...Spacious, full AC, gorgeous views of Simpson Bay Lagoon

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$672

Best rated: SXM Panoramic Ocean View private villa w/exclusive private pool.

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$401

Match: Garden

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Price per night from

$183

1 or 2 weeks in condo 5 * St. Marteen seaview

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$210

MAEVA... Affordable, modern, completely new after Irma! Steps to beach!

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Garden

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Price per night from

$120

Gorgeous Beachfront Villa#9 at 'Villas on Great Bay'

Philipsburg apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$385

JOIE DE VIVRE... 3 BR With Privacy on a fabulous Beach. WOW!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$929

BLUE BEACH VILLA... 4 BR villa on gorgeous white sandy beach!

Terres Basses house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$1,250

JUST IN PARADISE... Luxurious, Modern, Gorgeous Views

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$943

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$915

Villa Flagrantia

Philipsburg house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Garden

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Price per night from

$224

LA FAVORITA ...Absolutely Gorgeous Contemporary St Martin Rental Villa In The He

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$843

GREYSTONE...beautiful French Caribbean-style villa surrounded by lush tropical g

Terres Basses villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$407

BAHIA BLUE ... Fun, modern 4 BR villa w/ full AC, walk to beach, heated pool!

Sandy Ground house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$743

Match: Garden

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Price per night from

$298

Dawn Beach Club, St.Maarten - Ocean Front, next to JWMarriott property

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Garden

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Price per night from

$573

LUNE DE MIEL....The Honeymoon! Romantic hideaway for lovers

Terres Basses house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$543

GRANDE AZURE ... Spectacular 5 BR villa, views! huge heated pool, tennis, full A

Terres Basses villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$5,115

BAHARI... Fabulous beachfront villa, breathtaking sunsets!

Cupecoy Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Amazing and relaxing” This home has everything! Great beaches, restaurants and shopping are all nearby but no need to leave the house. Beachfront, pool, amazing sunsets, designer furnishings, hot tub and state-of-the art kitchen, wireless network, music system, computer games and flat-screen televisions.. . including a huge outdoor television for night-time viewing from the pool! It is now our family's annual vacation spot!

Match: Garden

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Price per night from

$680

Octagon Villa

West End Village villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$458

Spacious Private Villa, Ocean Views, Concierge

Oyster Pond house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

“Extremely relaxing and comfortable” The house is located within walking distance to the beach, restaurants, and entertainment. With a great view of St., and the sun rise, you can enjoy your morning coffee while deciding which beach or sights to see that day. The house has plenty of room for you and your extended family. It is configured strategically to allow for the whole family to enjoy each others company, as well as provides quiet areas such as the back garden to commiserating with the turtles. Maureen was such a great help with getting situated in the house

Match: Garden

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Price per night from

$492

BEAULIEU... Lovely Villa with Stunning Views! Heated Pool!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$1,300

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rentals in Guana Bay

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