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Villa vacation rentals in Happy Bay

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Popular amenities for Happy Bay villa rentals

Private villa rentals

Top guest favorite
Villa in MF
4.99 out of 5 average rating, 91 reviews

Your Paradise Villa

YanRating, 5 stars1 week ago
We had an absolutely amazing week at Your Paradise Villa in St. Maarten! The villa was stunning, perfectly clean, and had breathtaking views. Every detail was thoughtfully arranged, making our stay incredibly comfortable and relaxing. We can’t wait to come back! We would like to extend our heartfelt thanks to Denis, the gracious owner of Your Paradise Villa. Your exceptional hospitality and thoughtful gestures made our stay truly unforgettable. The special gifts and treats you provided were delightful surprises that added a personal touch to our experience. Your attention to detail and genuine care ensured that every moment of our week in St. Maarten was filled with comfort and joy. Thank you, Denis, for going above and beyond to make our vacation so special.
Guest favorite
Villa in Pelican Key
5 out of 5 average rating, 5 reviews

Oceanview Oasis - Villa Del Sol W/Generator

TinaRating, 5 stars1 month ago
Great place with an amazing view. Could walk to town in 20mins. House was perfect for our group with en-suite bedrooms. The pool was great. Saul was very responsive and friendly.
Guest favorite
Villa in Upper Prince's Quarter
4.98 out of 5 average rating, 60 reviews

Sea Haven Villa - Breathtaking Views of Dawn Beach

KristaRating, 5 stars1 month ago
Our stay at Sea Haven was amazing! We had great weather and could walk down and swim at Dawn Beach almost every afternoon. My kids enjoyed swimming in the pool everyday, nighttime swimming was their favourite! The home was in a great location but definitely need a car. Sleeping accommodations worked out well for us, my parents stayed in the bedroom in the main house, my 2 kids and us in the two bedrooms underneath. I would definitely return and stay again. Thank you Esheen for making our stay so wonderful and stress-free!!
Superhost
Villa in Cul-de-Sac
4.88 out of 5 average rating, 26 reviews

Villa Chloé SXM – Beachfront & Pinel View 🌴☀️🐬

AlexRating, 5 stars2 months ago
The house was great! Very clean, beautiful kitchen, amazing outdoor living space, great views and loved the access to the water! We came with two couples and two toddlers and the place had everything we needed! Perfect location right on the water, close to Orient Beach area and very easy to get to Pinel Island either by kayak or by the ferry boat. We will definitely stay again! Thank you!
Superhost
Villa in Orient Bay
4.85 out of 5 average rating, 65 reviews

Villa BO Beach, private pool, 2+1 bedrooms

HeatherRating, 5 stars2 months ago
Second time staying and the hosts were awesome as usual, very responsive! We will be back!
Superhost
Villa in Sint Maarten
4.84 out of 5 average rating, 63 reviews

Villa Indigo Dream, Indigo Bay SXM

GayleneRating, 5 stars2 months ago
We had a wonderful stay at Laura’s place! What an amazing setting with a view that you could look at all day and night long! We spent most of our time next to the infinity pool and couldn’t get enough of it. A quick trip down the hill to the local beach and restaurant provided a nice change of scenery (not that it was needed). The house is perfectly appointed with everything you need. We were met upon arrival by their friendly staff. Communication was perfect and we had a great kitchen and very comfortable bedrooms. Highly recommend Laura’s place!
Superhost
Villa in Collectivité de Saint-Martin
5 out of 5 average rating, 3 reviews

Villa Litchi | Collection Villas Saint-Martin

OnurRating, 5 stars1 month ago
One of the best stays I’ve ever had on Airbnb! The villa was even more beautiful than the pictures — spacious, clean, and thoughtfully designed. I especially loved the stunning view and the outdoor shower, which made the experience feel even more special. Our host Marie was incredibly friendly and helpful, making us feel welcome from the moment we arrived. I wouldn’t hesitate to stay here again. Highly recommended!
Guest favorite
Villa in Philipsburg
4.99 out of 5 average rating, 269 reviews

Villa Dream View Belair Sint Maarten SXM

BernadetteRating, 5 stars1 week ago
Our family had a wonderful vacation. The villa was everything that we could have hoped and dreamed for. Everything that was listed in the description is accurate. Eric was always very accommodating and responsive. We appreciated the thoughtful goodies that he provided once we arrived to the island. The villa is in a safe area and we enjoyed exploring the island by renting a car. It is helpful to have at least a compact SUV in order to drive to the villa due to the steeper inclines.

Luxury villa rentals

Superhost
Villa in SX
5 out of 5 average rating, 3 reviews

Sea Esta - Luxury Oasis in Shore Pointe

BradRating, 5 stars33 months ago
We had an incredible time in St Maarten. The whole process with the Sotheby’s team was wonderful. They were incredibly helpful in preparing for our arrival, arranging for airport pickup, groceries and rental car waiting at the villa and concierge recommendations and help throughout our stay. The location of the villa was an incredible and central “home base” and we enjoyed being able to walk to Cupecoy Beach and the several nearby restaurants in the adjacent village development. 10/10 for convenience. Loved being close to so many things on both the French and Dutch sides. We hope to return soon and wouldn’t hesitate to recommend the place and the Sotheby’s team!
Guest favorite
Villa in Collectivity of Saint Martin
5 out of 5 average rating, 29 reviews

OOF architect's villa, sea view facing Pinel Island

LynnRating, 5 stars1 month ago
We loved staying here. The location was quiet and peaceful but can get to many places within 10 minutes. The property was beautiful and nothing was better than having a cup of coffee in the morning and overlooking the bay. Sylvie was also amazingly accommodating and worked with us through our flight diversion and getting in late. I would totally come back again and we loved every minute!
Guest favorite
Villa in Saint-Martin
4.95 out of 5 average rating, 20 reviews

Villa Pineapple - Grand Case Area -5mn Orient Bay

DicksonRating, 5 stars1 month ago
A great villa, centrally located just outside Grand Case. Spotless and well equipped. Véronique was very responsive to any and all questions. Highly recommend!
Superhost
Villa in Saint-Martin
5 out of 5 average rating, 3 reviews

Villa with sea view and heated pool

JaniqueRating, 5 stars14 months ago
We absolutely loved staying at this villa for many reasons. First, its location and three features we appreciated: it is on the west side of the island which means we saw beautiful sunsets every night; it is near Friar’s Bay Beach that we enjoyed a lot, including delicious food and great music at the Friar Bay Beach Café (quick note: you can walk to Friar’s Bay through the road - probably a 10 mins walk - but with the heat, we preferred to drive); and finally, it is secure and very private - we did not see nor hear neighbours. Second, its comfort. We spent most of our time outside, either in the pool or the covered patio. We also made friends with the turtles! The villa is well equipped with all we needed. And I would be remiss not to mention Julia’s quality service. She welcomed us at the villa and was very efficient to explain all its features. It was easy to communicate with her. Merci Julia!
Top guest favorite
Villa in MF
4.96 out of 5 average rating, 57 reviews

Private Orient Bay Villa with Spectacular Views

MimRating, 5 stars1 week ago
We had an absolutely wonderful stay. This was our first time to St. Martin. The house was perfect for us and even more beautiful in person. The view is amazing. They island was amazing. A short walk down the hill to access the beach, restaurants and stores was great. Dan and Flo were wonderful, helpful and very responsive. Would highly recommend this house to anyone looking to stay in this area. We can't wait to come back!
Top guest favorite
Villa in Sint Maarten
5 out of 5 average rating, 9 reviews

Indigo Oceanfront Condo Poolside - Unit 1

IvanRating, 5 stars1 month ago
From the breathtaking view to your own private pool, this is one of the best Airbnb you could ever stayed in. The location is amazing as it is nestled within a very quiet neighborhood on the Dutch side. Perfect for our family with three young children with plenty of room to enjoy the beautiful island
Top guest favorite
Villa in Saint-Martin
4.96 out of 5 average rating, 23 reviews

Spectacular sea view, direct access to the beach

AthalieRating, 5 stars2 months ago
Can't say enough good things about our stay AND about working with Sarah. She was patient and full of good info, and always replied quickly when we had a question. The house has an excellent design with plenty of living spaces to hang out - both indoors and outdoors. Loved the pool too.
Top guest favorite
Villa in Sint Maarten
5 out of 5 average rating, 23 reviews

Villa Vanille Luxury 3 Bedroom Indigo Bay

HermioneRating, 5 stars2 weeks ago
We had such a wonderful stay. The villa is absolutely beautiful and the views really are incredible. Marina and Yael were extremely helpful, even organising groceries at the house for our arrival. Would definitely come again!

Villa rentals with a pool

Guest favorite
Villa in ORIENT BAY
4.95 out of 5 average rating, 22 reviews

Orient Bay villa

WilliamRating, 5 stars6 days ago
Great place for a family with kids. 3 big rooms. A big living room area off the kitchen to hang out in. Great to have a pool when little ones are napping. The lounge chairs are super comfortable. Very walkable. Minutes to the beach and restaurants. A 5 minute drive to the big super market. 10 minutes to Anse cove and the Pinel island ferry. Super convenient and tons to do we couldn't do everything we wanted. Will be back.
Guest favorite
Villa in Saint-Martin - Orient Bay
5 out of 5 average rating, 6 reviews

Hidden paradise: comfort, pool, lush nature

ThomasRating, 5 stars4 weeks ago
We had an amazing stay at this property! The location was absolutely perfect—just a short walk to local shops, restaurants, and the beach, making it so convenient for everything we wanted to do. The home itself was top-notch—spacious, clean, and beautifully decorated. It had everything we needed for a comfortable and relaxing stay. The highlight, though, was definitely the pool! It was pristine and the perfect spot to unwind after a day of exploring. I highly recommend this place and can’t wait to return!
Villa in Cul-de-Sac
4.85 out of 5 average rating, 33 reviews

Ocean front "colibris" amazing view

LukasRating, 5 stars1 month ago
It was a perfect place to enjoy the view with the pool. The house was big enough for 6 people. Orient bay is 5 min away for restaurants and beach. We had a wonderful 2 weeks! The host was really reactive to our demands. We will be back!
Villa in Collectivité de Saint-Martin
4.8 out of 5 average rating, 5 reviews

Villa OB – Luxury, Pool & Close to Beach

JohnRating, 5 stars14 months ago
The villa was great. Very private except for the cameras. Make sure you ask up front for enough keys and remotes for the gate. Very comfortable beds. Great pool. Fantastic place to stay.
Superhost
Villa in Orient Bay
4.93 out of 5 average rating, 14 reviews

Villa Saphir, 3 bedrooms, private pool and beautiful view!

MollieRating, 5 stars16 months ago
Christine’s place is beautiful. The location is fantastic, as it feels both quiet and peaceful and private, and yet close to anything and everything you might need/desire. It is a great space for a family (we traveled with two small children). Christine’s place is well-stocked with anything you might need, from spices in the kitchen to pool toys, a first aid kit, and other amenities. Highly recommend!
Villa in Simpson Bay
4.75 out of 5 average rating, 44 reviews

Villa Sunset : very close to two beaches !

ChrisRating, 5 stars3 months ago
Great location and also great communication with very responsive host. Easy walk to many beaches, restaurants and bar.
Villa in Sint Maarten
4.89 out of 5 average rating, 45 reviews

Ocean front villa, pool, private ocean snorkeling

KenlynRating, 5 stars13 months ago
We've been to St Maarten at least 12 times. We've never stayed in this area, usually Simpson Bay. We loved it, close to everything. The place has an amazing view and pool. Nadine made check-in very easy and check-out. The place makes it comfortable. Everything was clean. As others have reviewed, a little worn, but certainly did the job. Plenty of places to get sun or hide out in the shade. For the money, a few things could be stepped up a bit: glassware ( one wine glass, the rest water glasses), silver ware, the master mattress was a rock, and few other things. I would rent it again.
Guest favorite
Villa in Sint Maarten
4.98 out of 5 average rating, 60 reviews

Villa Crystal Clear - Luxury Villa w/ Private Pool

CeliaRating, 5 stars3 months ago
This was my first time staying at an Airbnb and I’m converted! Crystal was an amazing host and so responsive and helpful. I felt as though I’ve known her for years! Her place was amazing and the views are breathtaking. Waking up to seeing blue water and three different islands from multiple rooms was just unreal. The private pool was A+ and my entire family loved every second of privacy and exclusivity. The neighborhood is quiet and the surrounding newly built homes at night was just a beautiful sight. The rooms were comfortable, the kitchen was super spacious and had every single thing we needed on a daily basis. Crystal was flexible with my concerns and always responded super fast on messenger. I felt like I was at my own home! She was a blessing and I will definitely return to her place again! 10/10!!!! Thanks again, Crystal <3
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