Vacation rentals in North Side

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Top-rated vacation rentals in North Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Condo in Simpson Bay

4.78 out of 5 average rating, 156 reviews

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

Guest favorite

Home in Sint Maarten

5 out of 5 average rating, 21 reviews

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!*

Superhost

Condo in Meads Bay Beach

5 out of 5 average rating, 3 reviews

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.

Guest favorite

Condo in Simpson Bay

5 out of 5 average rating, 24 reviews

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.

Guest favorite

Home in Marigot

5 out of 5 average rating, 6 reviews

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.

Superhost

Apartment in Upper Prince's Quarter

4.75 out of 5 average rating, 12 reviews

The Tree House SXM

Want to life a sunny vacation in the beautiful Caribbean Island of St. Maarten, 15 minutes near the beaches and the center of Philipsburg. With unrivaled point-blank views of the Caribbean Sea, set within a meticulously renovated old villa in a quiet residential area, this fully furnished one bedroom apartment is a rare gem. Including Wi-Fi, A/C and the bedroom is appointed with a built-in closet. Best of all is the outside porch with stunning ocean views and a unique cruise ships vista.

Superhost

Home in Les Terres Basses

5 out of 5 average rating, 5 reviews

Villa Ellia - Modern luxury in St Martin FWI

Located in the prestigious Lowlands, this villa is your dream vacation spot with its breath-takings views on our beautiful green mountains. The villa is 5 minutes away from beaches, supermarkets, gyms, and activities. We will take great pleasure in hosting you. When renting with us you get concierge services to facilitate all things during your stay. Villa Ellia has 4 bedrooms and 4 bathrooms, the master bedroom and the kitchen have direct access to the large terrace and the private pool.

Superhost

Apartment in Collectivity of Saint Martin

4.91 out of 5 average rating, 11 reviews

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 !

Guest favorite

Apartment in West end

4.91 out of 5 average rating, 77 reviews

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

Superhost

Condo in Pelican

4.68 out of 5 average rating, 62 reviews

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 apartment boasts breathtaking panoramic views of the turquoise waters and the endless horizon.

Superhost

Apartment in Sint Maarten

5 out of 5 average rating, 6 reviews

Pelican Key 1BR Townhouse

My place is close to the beach, family-friendly activities, nightlife, public transport, and the airport. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, solo adventurers, business travelers, and families (with kids). Caribbean Weeks has many units all over the island both smaller and larger then this one.

Superhost

Villa in Lowlands

4.87 out of 5 average rating, 15 reviews

Reflection Y 5 Star Villa

Our modern style will surely have you feeling like you are living in the lap of luxury. One-of-a-kind panoramic view in this 5-Star Villa! Conveniently located nearby the beautiful Mullet Bay Beach, Casinos, restaurants, shopping in the Maho Village, and the world-famous plane landing experience at the airport. Car Rental deals available upon request and an all-around vacation package!