Windward Vacation Rentals, Houses & More


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Areas near Windward

Great rentals within 20 miles that match your search

1 / 28

Caribbean Princess #C1 Superb apartment behind Orient Bay Beach

  • 2
  • 4
  • Min stay varies

$194

Details

1 / 35

Villa SAS - St Jean, St Barts

  • 2
  • 4
  • 7 nights min

$823

Details

1 / 11

3 Bedrooms, 2 Baths Condo At Dawn Beach

  • 3
  • 8
  • 7 nights min

$425

Details

1 / 13

LODGE " Au fil de l'Eau" - Sea View & Pool

  • 1
  • 3
  • Min stay varies

$165

Details

1 / 30

Ideal for Couples & Groups, Walk to Dawn Beach & Restaurants, Private Pool

  • 4
  • 8
  • Min stay varies

$780

Details

1 / 18

Villa Coralia with panoramic ocean view ,5 bedrooms or 4 bedrooms.

  • 5
  • 10
  • Min stay varies

$704

Details

1 / 24

Villa Akaroa - Saint Barts

  • 3
  • 6
  • 6 nights min

$426

Details

1 / 44

RESIDENCE**** ADAM & EVE / RENT DE 3 à 6 CHAMBRES

  • 6
  • 16
  • Min stay varies

$599

Details

1 / 13

Villa Harbour Light - Saint Barts

  • 2
  • 4
  • Min stay varies

$568

Details

1 / 24

Amérindiens 611

  • 2
  • 4
  • Min stay varies

$192

Details

1 / 23

Apartment Playa, Orient bay 1mn walk from beach and Village

  • 2
  • 6
  • Min stay varies

$159

Details

1 / 15

VILLA 3 rooms panoramic sea view with pool

  • 3
  • 6
  • 7 nights min

$267

Details

1 / 38

SKYWALKER...gorgeous oceanfront condo on St Maarten's

  • 2
  • 4
  • Min stay varies

$710

Details

1 / 16

You Villa Agave

  • 1
  • 2
  • Min stay varies

$397

Details

1 / 32

Sunset view, Orient beach condo with pool

  • 1
  • 2
  • 7 nights min

$64

Details

1 / 25

Côté Mer : Charming 1 bedroom 1st line ocean front

  • 1
  • 4
  • Min stay varies

$118

Details

1 / 8

skyblue seasonal rental cottage

  • 1
  • 2
  • 3 nights min

$83

Details

1 / 23

St Barth Villa Rental 1 bed Pool Sea View Located in Marigot

  • 1
  • 2
  • 7 nights min

$384

Details

1 / 44

Beautiful beachfront at The Villas On Great Bay

  • 2
  • 6
  • 3 nights min

$249

Details

1 / 18

Mapou, Sleeps 4

  • 2
  • 4
  • Min stay varies

$822

Details

1 / 31

APRIL SALES - 30% - Le COZI - SEA VIEW & BEACH FRONT

  • 1
  • 4
  • Min stay varies

$159

Details

1 / 26

Villa Eden Island, 3 bedroom

  • 3
  • 6
  • Min stay varies

$851

Details

1 / 11

Beachfront Villa in a Private Domain Luxury

  • 2
  • 4
  • 7 nights min

$780

Details

1 / 17

Perfect Pelican Escape -- Spectacular Views & Best Sunset Happy Hour

  • 2
  • 4
  • Min stay varies

$125

Details

1 / 16

STUDIO SEA VIEW EAST BAY WITH POOL GIVING ON THE BEACH

  • Studio
  • 4
  • 7 nights min

$125

Details

1 / 23

VistaRoyale - Private pool and breathtaking view

  • 2
  • 4
  • 7 nights min

$224

Details

1 / 26

VILLA BE SXM CUL DE SAC 180 ° SEA VIEW

  • 4
  • 8
  • Min stay varies

$288

Details

1 / 0

Acamar (ACA)

  • 3
  • 6
  • Min stay varies

$1772

Details

1 / 13

Villa TED

  • 2
  • 4
  • 7 nights min

$712

Details

1 / 0

Maracuja (MJA)

  • 3
  • 6
  • Min stay varies

$851

Details

1 / 8

Orson Villa

  • 2
  • 8
  • Min stay varies

$176

Details

1 / 17

TORTOLA 5106 views T1 sea and walk in water

  • 1
  • 4
  • Min stay varies

$83

Details

1 / 26

Le Beach Loft , perfectly located in the hart of Orient Beach and affordable!

  • 1
  • 4
  • Min stay varies

$110

Details

1 / 14

Beautiful and spacious Villa at 100 m from the beach!

  • 3
  • 6
  • Min stay varies

$235

Details

1 / 11

Nice and calm apartment in 0rient Bay

  • 2
  • 6
  • 3 nights min

$153

Details

1 / 33

BelAmour, a St. Barths Luxury Villa for Lovers

  • 1
  • 2
  • Min stay varies

$890

Details

1 / 20

La Plage

  • 7
  • 14
  • Min stay varies

$7740

Details

1 / 18

Villa Tranquille

  • 3
  • 6
  • Min stay varies

$719

Details

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