Vacation rentals in Simpson Bay

4.78 out of 5 average rating, 153 reviews

Condo in Simpson Bay

Oceanfront w private Pool | Beach 1 street away

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

5 out of 5 average rating, 14 reviews

Home in Sint Maarten

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Welcome to paradise in Indigo Bay, St. Maarten! Our brand new property offers ultimate indoor-outdoor living with sliders opening to breathtaking sea views. Open-concept layout, fully-equipped kitchen, private pool and courtyard, NO STEPS, and three ocean-view bedrooms. Experience luxury and comfort at our oceanfront villa. Book now for an unforgettable vacation! *There is construction of a new hotel in the bay. Noise has been minimal but is subject to change. Contact us with any questions!*

Condo in Meads Bay Beach

Beachfront 1 Bedroom Resort Condo with Terrace, Hot Tub & Stunning Views!

Tranquility Beach Anguilla is Anguilla’s newest beach resort on top-rated Meads Bay Beach on the West End and was voted Best Boutique Hotel in Anguilla 2023. Everything you need for an ultimate beach vacation is at your doorstep and our award-winning staff is at your service. Swim and snorkel in turquoise waters. Walk to resorts, spas and top restaurants. This unit is professionally managed by our friendly resort staff including property manager, concierge team, housekeepers and beach butlers.

5 out of 5 average rating, 19 reviews

Condo in Simpson Bay

Beachfront Caribbean Breeze in Paradise, SXM

Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to main stream. Amazing views . 2/2.5 with huge Master. Hear the waves flowing in onto the shore for those relaxing days and nights. New kitchen, living room area, bathrooms, dinning area with a Caribbean feel. Unwind on any balcony, penthouse ocean view, on daybed with a nice drink , looking over the verse tranquil ocean. Take a dip in the soothing crystal clear waters. Amenities enclosed & Wi-Fi included.

5 out of 5 average rating, 5 reviews

Home in Marigot

Sweet Home on the Beach.

SITUATION Exceptionnelle. Vue sur la baie de Marigot Pieds dans l’eau Face à la Mer des Caraïbes Superbe plage de sable blanc, cocotiers, mer turquoise ATOUTS Maison duplex sur la plage Situation idéale pour visiter 4 Piscines 1 tennis Un beau jardin Résidence sécurisée 24H/24H Parking gratuit A côté : supermarché, boulangerie, restaurants Idéal pour Couple Famille ou Amis BON A SAVOIR A 2 kms de Marigot Voiture location conseillée Wifi, forfait ménage, serviettes, draps inclus dans le prix.

4.94 out of 5 average rating, 33 reviews

Home in Phillipsburg

Villa Fleur de Mer Endless Ocean view /Priv. Pool

Villa Fleur de Mer is one of Sint Maarten's top-rated Villas. Private estate villa with a breathtaking 180-degree ocean view! Seclusion and tranquility, tempered by cool ocean breezes, with a private pool. Enjoy this adventurous yet tranquil paradise home between France and Holland. Spectacular views of the Atlantic Ocean with an unparalleled view of St. Barths. Minutes drive to downtown Phillipsburg and the French side. Enjoy the video below and Welcome, Home! https://fb.watch/7uxXstBra7/

5 out of 5 average rating, 16 reviews

Home in Cul-de-Sac

Waterfront property with water access & kayaks

Shallow turquoise waters, untouched island, beach clubs and cocktails, sand bank, pelicans and turtles. What else could you possibly need? Oh, yes: a place to stay. Villa Ti Case is a new 5 bedrooms waterfront holiday rental, located in a gated luxury residence occupied by private houses, holiday rentals and hotels. Less than 5 min drive to: French bakery, restaurants and beach bars, beaches, grocery stores, souvenir and clothing shops, boat charters, water sports, equestrian center, hikes.

5 out of 5 average rating, 11 reviews

Condo in Collectivity of Saint Martin

Bora Bora, on the beach, sea view 2 to 4 people

You dreaming of a vacation on the beach, you will not be disappointed. This apartment with direct sea view for 2 to 4 people is located in a quiet, secure and private residence, 4 swimming pools, tennis courts, parking lots. This little gem is fully equipped. At sunrise you will have your meals on a large terrace surrounded by palm trees, your feet in the sand admiring the beauty of the immense garden and in the evening before sleeping, the lights of the Island of Anguilla will transport you

4.9 out of 5 average rating, 10 reviews

Rental unit in Collectivity of Saint Martin

Just in paradise with lagoon's view

Situé au 2ème étage, avec une superbe vue, dans une charmante résidence à la Baie Nettlé Joliment décoré, tout confort, entièrement équipée et climatisé. D'une surface de 50m2, idéal pour une ou deux personnes (deux à deux places) , cet appartement peut accueilr jusqu'à 9 personnes (lit bébé et lits singles supplémentaires fournis sur demande) Coin salon Espace bureau salle à manger sur la terrasse Salle de bain avec baignoire Piscine refaite à neuf . Un coucher du soleil inoubliable !

4.91 out of 5 average rating, 74 reviews

Rental unit in West end

James Hughes nice place 2 bedroom upstairs

James Hughes apartment located in West end affordable and comfortable. we are close to maundays Bay Beach, shoal Bay West Beach, Barnes Bay beach, meads Bay Beach. we are also close to best buy supermarket. close to picante restaurants. excellent wifi. we have cars for rent $35per day we only take cash. we will take you back to the ferry or airport for free. Electric bikes for rent $25 per day. we also have scooters for rent $30per day. we can take you to the beaches and pick you up $30

4.82 out of 5 average rating, 67 reviews

Villa in Orient Bay

Villa Allamanda, sublime view, heated hot tub

Villa Allamanda is a very spacious house located in the secure Parc de la Baie Orientale, French side. It offers many assets for holidays for families or groups of friends: * Large terrace with pool, and its HEATED and overflowing JACUZZI * Spectacular view of the bay and surrounding islands * Beach, water activities and shops within a 10-minute walk * 4 bedrooms with private bathrooms * Bluetooth speakers around the pool, with USB charger * Wifi

4.75 out of 5 average rating, 55 reviews

Condo in Pelican

SeaLaVie Apartment with Private Pool

Welcome to the stunning St. Maarten Beachfront Apartment with Private Pool! This luxurious Airbnb property offers an unforgettable vacation experience in one of the most beautiful and sought-after destinations in the Caribbean. Perched on the pristine white sands of St. Maarten's exquisite Kimsha beach, this beachfront penthouse boasts breathtaking panoramic views of the turquoise waters and the endless horizon.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simpson Bay vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Simpson Bay's top sights

Maho Beach72 locals recommend

Carrefour Market, Sint Maarten61 locals recommend

Karakter Beach Bar/Restaurant48 locals recommend

Avantika36 locals recommend

Soggy Dollar Bar31 locals recommend

The RedPiano Lounge29 locals recommend

Other great vacation rentals in Simpson Bay

4.8 out of 5 average rating, 15 reviews

Villa in Sint Maarten

La Casa al Mare: cheerful 2 bedroom villa

5 out of 5 average rating, 18 reviews

Villa in Pelican Key

Villa Sea Forever @ Pelican Key - Paradise Awaits!

4.88 out of 5 average rating, 8 reviews

Townhouse in Cul-de-Sac

Villa Essentielle, 3 bedrooms and pool!

5 out of 5 average rating, 12 reviews

Home in MF

VILLA CECILIA

Villa in Saint-Martin

Sea view villa and Heated Pool

Rental unit in Lowlands

Magnificent spacious ocean-view luxury condo

5 out of 5 average rating, 39 reviews

Villa in Little Bay

Sugarbird Nest: Sunrise Ocean Views | Great Bay

Villa in Collectivity of Saint Martin