See all properties

Cliff House

Top rated by guests

Terrace/patio

Villa, 2 Bedrooms | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

Coffee/tea maker, full-size fridge, microwave, oven

Interior

Villa, 2 Bedrooms | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

9Outstanding

(3 Ratings)

"Muna, housekeeper, was lovely. Warm and friendly. Stacey, the manager, also warm and friendly and very responsive. The owner, John, was just the same too. Property could use some sprucing, mainly wa..."

Shawn

Don't miss out! Price and availability may change

9 / 10

Outstanding(3 Ratings)

Villa in Simpson Bay

4 guests · 1 bedroom · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

Well priced for this locationPriced under area average

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this villa rental

Situated on the waterfront, this welcoming villa brings all of Simpson Bay within your reach. Maho Beach and Maho Bay are just a short walk away.

Spend a day at the nearby beach, relax by the outdoor pool, or sip a drink on the furnished balcony of this villa. For a change of scenery, come inside and enjoy the free WiFi and TV.

A dining area, a safe, and air conditioning are featured at this 2-bedroom rental. Bathroom amenities include a hair dryer, towels, and shampoo. The kitchen is equipped with an oven, a stovetop, and a full-sized refrigerator/freezer, as well as a coffee maker, an electric kettle, and a microwave. And you can even travel light because you'll have a washer/dryer.

Amenities at Cliff House

Free WiFi/internet

Air conditioning

Pool

Non-smoking

TV

Bathroom

Coffee/tea maker

Kitchen

Balcony/Terrace

WiFi/Internet

Microwave

Dishwasher

Dryer

Kitchenware

No pets allowed

Kettle

Oven

Stove

Bath or shower

Family friendly

Children's high chair

Towels

Safe

Hairdryer

Map of Simpson Bay

city location on map

Nearby attractions

Rainforest Adventures St Maarten - Rockland Estate

Yoda Guy Movie Exhibit

Ratings and reviews

9 / 10

Outstanding(3 Ratings)

8 / 10Excellent·Mar 2025

Muna, housekeeper, was lovely. Warm and friendly. Stacey, the manager, also warm and friendly and very responsive. The owner, John, was just the same too. Property could use some sprucing, mainly water pressure and pool pump, however we learned it was an area outage. Overall, we loved the privacy and all the birds and iguanas and the setting is BEYOND beautiful!!

8 / 10Excellent·Mar 2024

Amazing location. Views of the bay and the ocean on each side. Walkable to Maho restaurants and grocery. Would stay again

5 / 10·Feb 2024

Great stay at the Cliff house. Very private accommodations and plenty of room for a couple or a family experience. Easy parking, but only a short 7 minute walk into town.

$$$$

FAQs

Is parking included with this villa?

Parking is not specified as an available amenity at Cliff House. For more information, we encourage you to contact the property about where to park.

Is there a pool at this villa?

Yes, a swimming pool is available for use at Cliff House. Enjoy the water!

Is Cliff House pet friendly?

Unfortunately, this villa is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Cliff House?

We found 24 amenities for this rental. This includes free wifi/internet, air conditioning, pool, non-smoking, and tv.

Explore similar stays in Simpson Bay

Explore all stays

9 / 10

Outstanding(3 Ratings)

Cliff House

4 guests · 1 bedroom · 1 bath

Free WiFi/internet · Air conditioning · Pool

This Villa in Simpson Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

6.6 / 10

Average(4 Ratings)

Garden View Condo in Maho

4 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Pool · Refrigerator

This inviting Apartment in Simpson Bay can fit your needs for many types of vacations, at $341 per night.

Beachfront

9.9 / 10

Outstanding(119 Ratings)

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!

6 guests · 3 bedrooms · 3 baths

Nestled in Simpson Bay, this Villa is perfect for your next vacation. Enjoy 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!'s top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

9.6 / 10

Outstanding(105 Ratings)

Oceanfront amazing 2 BR Villa - 2 min from the beach

4 guests · 2 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Simpson Bay at Oceanfront amazing 2 BR Villa - 2 min from the beach for $335 for your next trip.

9.4 / 10

Outstanding(49 Ratings)

Tradewinds at Simpson Bay

5 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Air conditioning · Pool

Soak up the beauty of Simpson Bay in our Apartment, Tradewinds at Simpson Bay. With a range of amenities such as Non-smoking, Air conditioning and WiFi/Internet, you'll feel right at home.

You can save with One Key

7.4 / 10

Good(3 Ratings)

Sunset Beach View - Luxury Studio next to The Morgan Resort

in Maho, Sint Maarten

4 guests · 1 bedroom · 1 bath

Business stays, family stays, couples stay, getaway vacation, and rental in Simpson Bay at Sunset Beach View - Luxury Studio next to The Morgan Resort for $261 for your next trip.

Beachfront

10 / 10

Outstanding(119 Ratings)

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!

6 guests · 3 bedrooms · 3 baths

Discover the beauty of Simpson Bay with a stay at 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!, a top rated Villa with amenities such as No pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

9.8 / 10

Outstanding(67 Ratings)

Oceanfront amazing 2 bedrooms Condo

4 guests · 2 bedrooms · 2 baths

When traveling to Simpson Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $296 per night.

9.6 / 10

Outstanding(105 Ratings)

Oceanfront amazing 2 BR Villa - 2 min from the beach

4 guests · 2 bedrooms · 2 baths

Looking for the perfect place to call home during your trip to Simpson Bay? This Villa offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.

La Madrague à Deux pas de la Plage

6 guests · 3 bedrooms · 2 baths

Experience the best of Simpson Bay with this House available for $369. This property is equipped with amenities including Pets allowed and Non-smoking, and more.

7.4 / 10

Good(3 Ratings)

Sunset Beach View - Luxury Studio next to The Morgan Resort

in Maho, Sint Maarten

4 guests · 1 bedroom · 1 bath

Apartment in Simpson Bay, for $261 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

You can save with One Key

9 / 10

Outstanding(2 Ratings)

The Maho Hideaway on Sunset "Airplane" Beach

6 guests · 1 bedroom · 1 bath

This Apartment in Simpson Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

9.8 / 10

Outstanding(67 Ratings)

Oceanfront amazing 2 bedrooms Condo

4 guests · 2 bedrooms · 2 baths

This Apartment for $296 in Simpson Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(1 Rating)

Maho Beach House: Sunset Suite, 1-Bedroom

5 guests · 1 bedroom · 1 bath

Looking for a Apartment in Simpson Bay, this Apartment for $341 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

9 / 10

Outstanding(2 Ratings)

The Maho Hideaway on Sunset "Airplane" Beach

6 guests · 1 bedroom · 1 bath

Soak up the beauty of Simpson Bay in our Apartment, The Maho Hideaway on Sunset "Airplane" Beach. With a range of amenities such as Pets allowed, Family friendly and Non-smoking, you'll feel right at home.

You can save with One Key

7 / 10

Good(2 Ratings)

Sunset Beach Condo- 1BR Lux home next to The Morgan Resort

5 guests · 1 bedroom · 1 bath

Discover the beauty of Simpson Bay with a stay at Sunset Beach Condo- 1BR Lux home next to The Morgan Resort, a top rated Apartment with amenities such as Pets allowed, Family friendly and Non-smoking, and more.

10 / 10

Outstanding(1 Rating)

Maho Beach House: Sunset Suite, 1-Bedroom

5 guests · 1 bedroom · 1 bath

This attractive Apartment in Simpson Bay, $341 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

8 / 10

Excellent(1 Rating)

Sovereign Suites Maho | 2BR w/ Pool, Beach Gear

6 guests · 2 bedrooms · 1 bath

This Apartment for $376 in Simpson Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

2BR Maho Oasis | Walk to Beaches & Nightlife!

6 guests · 2 bedrooms · 1 bath

Looking for a Apartment in Simpson Bay, this Apartment for $389 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

8 / 10

Excellent(1 Rating)

Sovereign Suites Maho | 2BR w/ Pool, Beach Gear

6 guests · 2 bedrooms · 1 bath

Nestled in Simpson Bay, this Apartment is perfect for your next vacation. Enjoy Sovereign Suites Maho | 2BR w/ Pool, Beach Gear's top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.

2BR Maho Oasis | Walk to Beaches & Nightlife!

6 guests · 2 bedrooms · 1 bath

Apartment in Simpson Bay, for $389 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

You can save with One Key

10 / 10

Outstanding(25 Ratings)

Maho Royal Islander, La Terrasse 2br 2ba Beautiful White Sand Beach

4 guests · 2 bedrooms · 2 baths

Discover the beauty of Simpson Bay with a stay at Maho Royal Islander, La Terrasse 2br 2ba Beautiful White Sand Beach, a top rated Apartment with amenities such as No pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

10 / 10

Outstanding(1 Rating)

3 Sea Vistas, Palm Beach Condos, Simpson Bay Beach

4 guests · 2 bedrooms · 2 baths

When traveling to Simpson Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $387 per night.

10 / 10

Outstanding(25 Ratings)

Maho Royal Islander, La Terrasse 2br 2ba Beautiful White Sand Beach

4 guests · 2 bedrooms · 2 baths

Looking to create some memories in Simpson Bay? Look no further than our Apartment, Maho Royal Islander, La Terrasse 2br 2ba Beautiful White Sand Beach. Enjoy top-rated amenities including No pets allowed, Family friendly and Non-smoking, and more.

Beachfront

10 / 10

Outstanding(3 Ratings)

Beachfront condo with pool

4 guests · 2 bedrooms · 2 baths

Looking for the perfect place to call home during your trip to Simpson Bay? This Apartment offers a comfort and style with top-notch amenities, including No pets allowed and Non-smoking, and more.

10 / 10

Outstanding(1 Rating)

Paradise by the Sea

4 guests · 2 bedrooms · 3 baths

Looking for a memorable stay in Simpson Bay? Our Apartment might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.

9.6 / 10

Outstanding(13 Ratings)

Paradise Gem, ground floor on Simpson Bay Beach!

4 guests · 2 bedrooms · 2 baths

This Apartment for $331 in Simpson Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

6.6 / 10

Average(4 Ratings)

Garden View Condo in Maho

4 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Pool · Refrigerator

Looking for a memorable stay in Simpson Bay? Our Apartment might just be what you're looking for. Enjoy amenities including Non-smoking, Balcony/Terrace and Dryer, and more during your stay.

You can save with One Key

9.6 / 10

Outstanding(13 Ratings)

Paradise Gem, ground floor on Simpson Bay Beach!

4 guests · 2 bedrooms · 2 baths

When traveling to Simpson Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $331 per night.

9.4 / 10

Outstanding(49 Ratings)

Tradewinds at Simpson Bay

5 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our Apartment in Simpson Bay has everything you need for a rejuvenating stay. Treat yourself to Tradewinds at Simpson Bay's exceptional amenities, such as Non-smoking, Air conditioning and WiFi/Internet.