Windward Rentals

/ Home
/ Vacation Rentals
/ Caribbean
/ St. Barthelemy
/ Windward
Book with confidence.

Updating...

age 0-16
349 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

349 Houses

Why am I receiving these results?

❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Balcony or terrace

All filters match

Price per night from

$1,148

Great rentals within 20 miles that match your search

3BDRM Beautiful Condo at Westin Dawn Beach Club

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$616

THE ROCK 2 New Seaview Duplex Condo with Jacuzzi !

Orient Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 32 minutes

Match: Balcony or terrace

All filters match

Price per night from

$185

Studio design bord de mer vue imprenable

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Balcony or terrace

All filters match

Price per night from

$136

Match: Balcony or terrace

All filters match

Price per night from

$645

Location Résidence Grand Luxe A St Martin

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$615

Orient beach Premium view Frontsea Studio

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Match: Balcony or terrace

All filters match

Price per night from

$100

Westin Dawn Beach Resort & Spa

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$493

LE PRIVILEGE...Huge 7BR Villa - Stunning Views of Marcel Cove

Anse Marcel villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$3,580

BOUGAINVILLEA...Fabulous views overlooking Dawn Beach & St. Barths

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$938

TRES CHIC... fabulous modern beachfront condo at Caribbean Riviera on Orient Bay

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Balcony or terrace

All filters match

Price per night from

$311

ESTHER... charming, new, affordable townhome with private pool, walk to Orient b

Orient Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect!!” We stayed at Villa Esther just last week. It's in a excellent location with walking access to Bikini Beach as well as La Playa which provides a free chair and umbrella, with drink purchase. The plunge pool is perfect for a cooling down after the beach. Wifi keeps you connected with home without massive cell charges, and the entire place is clean and functional. A/C works great on hot nights. Best part is your walking distance to some of the best cuisine on the island. It's all here at Villa Esther, as well as an outstanding staff to welcome you.

Match: Balcony or terrace

All filters match

Price per night from

$226

Lighthouse 3C...Featuring beautiful views of the ocean and Dawn Beach

Oyster Pond farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$502

Match: Balcony or terrace

All filters match

Price per night from

$351

BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Heated Pool!

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$2,807

HOPE COTTAGE... charming, romantic hideaway w/ breathtaking views!

Oyster Pond villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Balcony or terrace

All filters match

Price per night from

$216

VICTORIA...3 BR affordable St Martin rental villa, panoramic views

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$597

Match: Balcony or terrace

All filters match

Price per night from

$1,303

FIVE MINUTES MORE... Fabulous contemporary villa overlooking Oyster Pond

Oyster Pond house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Amazing Villa!” 7 of us stayed at this villa. Amazingly clean and the web photos don't do it justice. Re/max did a great job addressing a couple of minor issues. We would definitely stay here again!

Match: Balcony or terrace

All filters match

Price per night from

$802

Match: Balcony or terrace

All filters match

Price per night from

$673

MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Balcony or terrace

All filters match

Price per night from

$230

CORALITA...4 BR casual villa in French St Martin on Oyster Pond

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$476

IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$430

Match: Balcony or terrace

All filters match

Price per night from

$517

PARADISO... Stunning modern 6 BR villa with huge blue views!!

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$1,332

CASA DE BELLA... Great location at a great price!!

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$216

MACASSI 4... Sooo Cute & Affordable!! Walk To Orient Beach!

Orient Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$269

BEACH HOUSE YOUNES.. Oceanfront 2BR villa just steps from Dawn Beach

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice oceanfront villa” ???????? ????? ?? ??? ???? ??? ????? ? ?????? ? ???????? ???????. ???????? ??? ? ???????????? ??? ??????. ???????? ?????????? ? ??????? ??????????. ? ???? ???? ??? ??????????? ???????????? ? ??????????????. ???? Wifi ? ??????? ???????.????????? ???????? ?????? ???? ????? ?? ? ??. ?? ??????? ????? ????????? ???-?? ???????, ??? ?? ? ???????. ?????????? ?? ??????????? ??????? ? 30-40 ??????? ?? ????????? ? ? 10-15 ??????? ?? ??????????? ,???????? ?? ??????????? ???????. ???? Dawn beach ????? ??? ??????, ???? ??????? ??????, ????????? 3 ??????. ?? ?????? ??????? ????? ? OysterPond ???? ????????? ??????????. ? ???????? ????? ???? ? ????????,?????????????? ? ?????????. ?????? ????? ? ?????? ???????????, ?? ??????? ?????????? ????? ?????? ? ????????.

Match: Balcony or terrace

All filters match

Price per night from

$458

HOPE ESTATE...4 BR Deluxe Villa Overlooking Orient Bay

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$923

Match: Balcony or terrace

All filters match

Price per night from

$473

Match: Balcony or terrace

All filters match

Price per night from

$490

COSTA TURQUOISE... charming, very affordable, directly ON BEACH!

Orient Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Balcony or terrace

All filters match

Price per night from

$145

LATANIERS 12...affordable condo in the heart of Orient Village, St Martin

Orient Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

Match: Balcony or terrace

All filters match

Price per night from

$139

Match: Balcony or terrace

All filters match

Price per night from

$358

1 Bdrm Condo with Superlative Views of St. Barts

Philipsburg apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

Match: Balcony or terrace

All filters match

Price per night from

$230

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Balcony or terrace

All filters match

Price per night from

$632

Beautiful beachfront at The Villas On Great Bay

Philipsburg villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

“Super holiday at the Great Bay” Unfortunatly we have left Villa nr 2 past sunday after 12 wonderfull days! After the confirmation of our reservation we have never had a single doubt on this piece of heaven on earth, but it even exceeded all expectations!! Verry happy to stay here once more and already looking forward to that. This place is relaxing but has all comforts of a fully equiped villa on the other hand as well. Both Jim and Gina (on-site managers) do their very best to make the stay as comfortable as possible.

Match: Balcony or terrace

All filters match

Price per night from

$259

Villa Angelina Amazing Panoramic Views

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$319

Viewing 38 of 349
rentals in Windward

×

Also consider