Vacation rentals in Maundays Bay

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Top-rated vacation rentals in Maundays Bay

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Guest favourite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 56 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

Sep. 4 – 11

$868 CAD per night

Guest favourite

Condo in Meads Bay, Anguilla

5.0 out of 5 average rating, 7 reviews

Beach Resort 1 Bedroom Condo with Terrace, Hot Tub & Ocean View

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.

Oct. 17 – 24

$756 CAD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 36 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

SPECIAL: MARCH 18-30 @ $800/NIGHT Guaranteed to create a 5-Star experience! Fully air-conditioned 3 BR, 3 1/2 bath Beachfront Villa w/private pool. If you love the ocean & spectacular views, but fine living & comfort are important to you, we have it all! My home offers Personal housekeeper, Private Chef for hire, full Concierge Service, private garage, and gym. Also, food and groceries delivered prior to your arrival, access to all the services and amenities next door at the Oyster Bay Hotel.

Sep. 18 – 25

$1,256 CAD per night

Guest favourite

Apartment in Grand-Case, St. Martin

4.92 out of 5 average rating, 74 reviews

lovely 1 bedroom beach front property

Come stay in one of our comfortable apartments! our Apartment is located on the first floor ( and only floor) in one of saint-martin's most popular areas Grand case Boulevard, 2 min from Grand case airport, walking distance from a variety of popular restaurants, local dishes, boutiques and of course just a few steps from the private yard you'll be toes deep on the beach. You can also rent a car with us ( airport pick up included) so that you can get around the island. contact us for more info

Sep. 17 – 24

$152 CAD per night

Guest favourite

Apartment in Grand-Case, St. Martin

5.0 out of 5 average rating, 10 reviews

Charming appartment on the beach, 1 or 2 bedrooms

This new, comfortable and pretty appartment located on the beach, in the heart of Grand-Case has its own sandy garden, beach chairs and direct beach access . Enjoy a stunning full view on Creole rock and Anguilla. It's a privileged spot in town and even in the island. Sea view from your bed, from the salon/kitchen area, wide covered terrace with sofa, red wood deck and gazebo covered with real braided palm leaves. True caribbean style! * Charming decoration * * Great location * 2 bedrooms

Dec. 29 – Jan. 5

$729 CAD per night

Guest favourite

Apartment in West end , Anguilla

4.91 out of 5 average rating, 65 reviews

James Hughes nice place in West end

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 $30per 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 $25 per day. we can take you to the beaches and pick you up $30

Aug. 24 – 31

$150 CAD per night

Guest favourite

Guest suite in West End, Anguilla

4.94 out of 5 average rating, 50 reviews

Hummingbird, Charming Garden Studio, West End

Stylish, cool yet affordable accommodations in a fabulous location. EXCELLENT WIFI. Unbeatable value for lovers of Anguilla's West End! Safe for singles - romantic for couples - all welcome. Walk to beaches: Mead's, Barnes and Maunday's Bays & places like Four Season's & Picante. Beautiful indoor/outdoor kitchen/lounge area &tropical garden. Discounts for long stay. You must be VACCINATED to vacation in Anguilla. Please visit the Anguilla Tourist Board for current entry protocols.

Mar. 24 – 31

$259 CAD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 171 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Oct. 6 – 13

$433 CAD per night

Guest favourite

Condo in Collectivity of Saint Martin, St. Martin

5.0 out of 5 average rating, 63 reviews

Holidays in the Paradise on the Beach

Apartment with magnificent sea views Directly on Nettlé Bay beach with pool Close to shops Restaurant, bakery, pharmacy... 15 minutes from Juliana International Airport and Mullet Bay Golf Plage de Baie rouge et baie aux prunes 10 Minutes Although life on our Friendly island is very good , it is to be noted that electricity and water disruptions may happen please be assured that all concerned do their utmost to minimize any Inconvénience « Thank You 🥰

Aug. 10 – 17

$217 CAD per night

Guest favourite

Loft in Marigot, St. Martin

4.99 out of 5 average rating, 116 reviews

Sea Loft Stunning View - Private Pool

* 200m² Loft * Exceptional sea views * Private pool * 250 meters to small beach Galisbay * Terrace with sun loungers, garden furniture, garden furniture, outdoor table, and BBQ * Desk area * 100 Mbps WiFi * TV with thousands of channels from all over the world * A 250m walk to Marina Fort Louis de Marigot * 5 min walk to the city center of Marigot with its restaurants, shops and other shops * 5 min from the pier for St. Barts and Anguilla, and the taxi station

Sep. 5 – 12

$473 CAD per night

Guest favourite

Cottage in Cul-de-Sac, St. Martin

4.98 out of 5 average rating, 101 reviews

VILLA JADE 2: WATERFRONT/ POOL

VILLA JADE is a complex of 3 villas located in THE BAY OF ASS DE SAC and its islets ... VILLA JADE 2 is a spacious suite/sea view for 2 people seafront, with private pool. The 3 villas are adjoining but very quiet and intimate. Your only view is the sea... Direct access to the sea by a pontoon, and kayaks at your disposal.

Nov. 30 – Dec. 7

$472 CAD per night

Guest favourite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 224 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Oct. 16 – 23

$662 CAD per night