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Vacation rentals in Simpson Bay

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Simpson Bay

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

Condo in Marigot

Gorgeous studio ON THE BEACH,ocean view

BEAU STUDIO au 2 étage dans une résidence sécurisée,avec plage privée et accès directement par la résidence. Notre studio est l'endroit idéal pour passer de bonnes vacances.Une vue incroyable sur la mer turquoise des caraïbes et des couchers de soleil époustouflants.Il est entièrement équipé en cuisine et le linge de maison ,il y a un lit queen et un canapé lit Il as aussi le wifi et Tv. Il y a une épicerie à 200m,le parking est gratuit et nous sommes à 5 mn du ferry pour St Barth et Anguilla

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/

Rental unit in West end

James Hughes best price upstairs wonderful view

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

Rental unit in Simpson Bay

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

Le Petit Paradis - Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation, Hope to invite you soon in our Paradise, Elodie

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. New totally refurbished modern apartment with modern amenities and comforts. A perfect vacation spot !

Home in Pic Paradis

Newly Renovated! Villa Paradis - A jungle getaway.

Welcome to Villa Paradis, a different side of St. Martin! Discover breathtaking views and be surrounded by nature. A unique experience with iguanas in the trees and the sound of monkeys echoing through the valley. This exclusive property is the nature lover's paradise, ideal for those seeking to get away from it all while being centrally located only 10 mins from the beach. *Spa services/private chef available *No children *No parties Social Media: #theparadisepeak

Villa in Les Terres Basses

"La Maison de Vacances", Nearby Baie Longue

Relax in the Caribbean in the charming and comfortable "Maison de Vacances" near the most beautiful unspoiled beaches of the Antilles. ( Long Bay Beach- Plum Bay Beach - Red Bay Beach) Within the privileged and secured Domaine des "Terres Basses", Long Bay beach, 500m from the house by foot, where you can swim in peace, and you will enjoy exceptional sunsets. Take advantage of the renowned activities on the Dutch side or the excellent restaurants on the French side.

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.

Home in Collectivity of Saint Martin

Step to the Beach : on the Beach of Orient Bay

Ravissante villa en duplex directement sur la plage d'Orient Bay, très confortable et très bien équipée ! Décoration raffinée. Vue mer incroyable. Parfaite pour un séjour en famille ou entre amis. Equipée d'une citerne indépendante en cas de coupure d'eau. A quelques minutes à pied de la place du village avec ses restaurants, restaurants de plage, magasins, boulangerie, traiteur, coiffeur, petit supermarché.

Condo in Lowlands

Loft Condo - STEPS FROM BEACH!

Experience tropical luxury at our Mullet Bay vacation rental in Sint Maarten. Our 1BR loft boasts a queen bed, full kitchen, laundry facilities and a gated community complete with pool and barbecue area. Perfect for families or couples seeking a tranquil escape. Enjoy the comfort of spacious bedrooms and the convenience of on-site amenities. Book now for the ultimate island getaway!

Rental unit in Lowlands

Modern Studio in gated Resort pool & gym.generator

This Resort-like living Studio is close to the island main attractions, Mullet Beach, Maho night life area, Casino Royale, shops, supermarket. 5 minutes drive from international airport. Walk to the beach, restaurants and nightlife. Sports club next door, padel, soccer, pickleball. Pool, bbq, gym, bakery, fitness center, sand volleyball on property.

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Simpson Bay vacation rentals

Stay near simpson bay's top sights, other great vacation rentals in simpson bay.

Home in Calabash Rd, Cole Bay

THE HILL HOUSE, 2 Bdr, pool, panoramic view

Villa in Indigo Bay

Villa Life is Good

Rental unit in Philipsburg

Amazing modern duplex ocean view "Colosseo"

Villa in MF

Private Orient Bay Villa with Spectacular Views

Villa in Collectivité de Saint-Martin

Slowlife Harmony - Caribbean Villa Three Bedrooms!

Home in St Martin

Blue mornings private pool great view

Home in Philipsburg

Villa Allamanda a Indigo Bay

Villa in Cul-de-Sac

Pinel villa sea view 3 Bedrooms hot tub pool

Quick stats about vacation rentals in Simpson Bay

Total rentals.

320 properties

Nightly prices starting at

$27 CAD before taxes and fees

Total number of reviews

8.5K reviews

Family-friendly rentals

140 properties are a good fit for families

Pet-friendly rentals

50 properties allow pets

Rentals with a pool

210 properties have a pool

Destinations to explore

• Grand Case   Vacation rentals
• Gustavia   Vacation rentals
• Philipsburg   Vacation rentals
• Bakers Bay   Vacation rentals
• Marigot   Vacation rentals
• Cul-de-Sac   Vacation rentals
• Anse Marcel   Vacation rentals
• Anegada   Vacation rentals
• Basseterre   Vacation rentals
• Cole Bay   Vacation rentals
• Nail Bay   Vacation rentals
• San Juan   Vacation rentals
• Family-friendly rentals   Simpson Bay
• Serviced apartment rentals   Simpson Bay
• Fitness-friendly rentals   Simpson Bay
• Smoking-friendly rentals   Simpson Bay
• Beachfront rentals   Simpson Bay
• Rentals with beach access   Simpson Bay
• Rentals with pools   Simpson Bay
• Kid-friendly rentals   Simpson Bay
• Pet-friendly rentals   Simpson Bay
• Rentals with a patio   Simpson Bay
• Rentals with outdoor seating   Simpson Bay
• Apartment rentals   Simpson Bay
• House rentals   Simpson Bay
• Beach condo rentals   Simpson Bay
• Monthly Rentals   Simpson Bay
• Condo rentals   Simpson Bay
• Rentals with a washer and dryer   Simpson Bay
• Waterfront rentals   Simpson Bay
• Rentals with a hot tub   Simpson Bay
• Villa rentals   Simpson Bay
• Yurt Rentals   United States
• Yurt Rentals   United Kingdom
• Castle Rentals   United States
• Houseboats   United States
• Holiday Caravans   United Kingdom
• Private Island Rentals   United States
• Farm Houses   United States
• Farm Cottages   United Kingdom
• Cabin Rentals   Australia
• Luxury Cabins   United Kingdom
• Luxury Cabins   United States
• Holiday Chalets   United Kingdom
• Cottage Rentals   United States
• Holiday Cottages   United Kingdom
• Mansion Rentals   United States
• Villa Rentals   United Kingdom
• Holiday Bungalows   United Kingdom
• Bungalow Rentals   United States
• Condo Rentals   United States
• Holiday Apartments   Australia
• Holiday Houses   United States
• Holiday Houses   United Kingdom
• Private Holiday Rentals   United Kingdom
• Big House Rentals   United States
• Big Cottages   Australia
• Large Villas   United Kingdom
• House Rentals with a Pool   United States
• Cabin Rentals with a Pool   United States
• Villas with a Pool   United Kingdom
• Apartments with a Hot Tub   United States
• Holiday Cottages with a Hot Tub   United Kingdom
• Beach Cabins   United States
• Beach Condos   United States
• Beachfront Rentals   United States
• Beach Houses   United Kingdom
• Beach Villas   United Kingdom
• Coastal Cottages   United Kingdom
• Pet-Friendly Vacation Rentals   United States
• Pet-Friendly Beach Rentals   United States
• Pet-Friendly Cabin Rentals   United States
• Dog-Friendly Cottages   United Kingdom
• Luxury Dog-Friendly Cottages   United Kingdom
• › Sint Maarten ›
• › Simpson Bay

Beachfront vacation rentals in Montego Bay

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Montego Bay

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

Condo in Montego Bay

Sabal at One Palmyra your own personal retreat

Located on the Jewel Grande Spa & resort with all amenities on the 3rd floor of the owner building. Options for all-inclusive food and beverage offered by the hotel at check-in. IT IS NOT MANDATORY. All inclusive is $180 per person per day. Must book for entire stay or only for last day. Infants are free. Children 5-7 $75 per person. Day Pass (11:00am-5:00pm includes (Lunch) and Night pass (6:00pm to 11:00pm) and includes Room Service for $125 per person per day. Ask at time of Check-in.

Beach View Balcony Vacation Condo Best Location

PLEASE READ THE FULL DESCRIPTION BEFORE INQUIRING Newly renovated, open-floor, light-filled Studio apartment with a fully equipped kitchen and washer in a safe and secure building with a large balcony and stunning view. Ideally located on the Hip Strip, right across from Doctor's Cave Beach, Starbucks, Post Office, and an ATM. A short walk from local restaurants, casino, smoking lounges, and clubs, 10 minutes drive from the Airport 24/7 security, roof-top pool, free Wi-Fi, and free parking

Luxury Beachfront Condo at a Popular Resort

This luxurious well appointed 1 bdm condo is located at the Jewel Grande. Pristine white sand beaches of the Caribbean, cradled by lush tropical mountains and the warm ocean air make this a picturesque property. The large private terrace is the perfect place to relax. There are 3 world-class golf courses just minutes away...White Witch, Cinnamon Hill, and Half Moon. Guests have full access to Jewel Grande grounds. The condo features a fully equipped kitchen with necessary cooking utensils.

Rental unit in Montego Bay

Waterfront 2 Bed 2 Bathroom Apartment

A second-floor two-bedroom apartment with un-obstructed views of the sea. Each bedroom is air-conditioned with ensuite bathrooms. Located on the Freeport peninsula in the Bay Pointe gated community with 24-hour security. You have access to two large pools, sun loungers, and a Gazebo/ BBQ. You have free access to a tranquil private beach 5-10 min walk down the road. There is also a dedicated parking spot directly outside the apartment for easy access up the stairs and into the kitchen.

2BR Getaway w/Pool, Near Beach in Montego Bay

This gorgeous apartment has been furnished to feel like a true getaway. It’s the ideal retreat for an adventurous & up-scale stay, located in a gated community that is close to the absolute heart of Montego Bay. We believe it’s the ultimate location to experience this part of the island. At only 10 minutes walking distance from Doctor's Cave Beach and the main Hip Strip, you will be very close to all the action. Settle in by zoning out with family or friends and enjoy your getaway.

'Moscow' in MoBay, Artsy Apt in Beach Resort Area

This eclectic, Big City themed apartment will tantalize your senses and take you far away from your comfort zone. Creatively integrating images from cities around the world, prepare to be transported across seas and time zones. This 1 bedroom apartment is called “Moscow” and it is located in 22 Freeport, Montego Bay, on the most sought after upscale Freeport peninsula. This gated complex features beach front views, exercise classes, 24-hour security, infinity pool and playground.

Villa in Montego Bay

Villa Maria Montego Bay, Beach front with Pool

Villa Maria: A True Jamaican Experience (one of few Beach front villas in Mobay Fully staff Fully A/C Chef service available Up to 2 free airport pick-up and drop-off from MBJ. Property : We are located in a seaside fishing village. Even though not needed, we are monitored by security and outside video 24-hour OPTIONAL FEE The following fee is paid in addition to and after the reservation is paid for $180 / per day for pool heater. This is only if you want the pool heated.

New studio unit close to airport, beach & hipstrip

Ultra modern and gated complex located 2 minutes drive from the Sangsters Intl. airport and walking distance from Montego Bay's world renowned Hip Strip and beaches. This unit also retains excellent privacy and quietness despite the hip strip basically being at your doorstep. Who says you can't have it all?! The unit has a fully stocked kitchen and wardrobe amenities and a free parking spot. What are you waiting on? Your dream destination awaits you at this lovely and cozy unit.

Seawind On The Bay Freeport Montego Bay

Seawind On The Bay is a safe gated community. The property has a pool and shared bar and grill with a covered community centre. The beach is a short distance away beside Secrets Hotel. A spectacular view of Montego Bay Harbor with cruise ships awaits you. Montego Bay Yacht Club is next door with great food and bar. Also, within walking distance is Secrets Wild Orchid, Breathless, and Sunscape Montego Bay Resorts and Spa. Montego Bay Cruise Ship terminal less than 2 miles away.

Jus' Beachy Deux Luxury Apt in B/Frnt Gated Comnty

Introducing Jus Beachy Deux - The 2nd beach theme apartment of our Jus Beachy units located on the upper floor in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground. Be sure to check out my other units in this community on my profile if your dates are not available here or if you would like to book both units for a party of up to 8 people.

Rental unit in St. James Parish

HideAway By the Sea - Your HOME away from Home

Welcome to HideAway by the Sea, where you will be able to relax and enjoy the island. This studio apartment offers all the comforts of home with AC, room fan, hot water on demand, a washer, Smart TV, WIFI, comfy Queen bed and a fully equipped cooking space to make meals. This space is great for working professionals, travelers, singles, or a couple. It is very safe with 24-hour security. Smoking is permitted on patios only.

Luxury Apt, Beach Front Resort Montego Bay Jamaica

Welcome to my vacation property! My luxury beach apartment is located in the Jewel Grande, a 5 star award-winning ultimate resort in Montego Bay Jamaica. An additional all inclusive meal plan option is available for purchase directly from the hotel which is designed to ensure that when you arrive you have no other obligation than to relax. Looking for paradise? You have found it!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Montego Bay beachfront rentals

Pet-friendly beachfront home rentals.

Modern Garden/Sea View Studio

Roots by Alex H

Condo in St.Bran's Burg

Montego Bay 2 br beach/ pool Condo inc roof patio

Bungalow in Montego Bay

victorious faith Ranch at west village

Vacation home in St James

Gafrris gardens

Private room in Montego Bay

The Housen Residence

❤️New Ocean Front Montego Bay Club Hip Strip Beach

1❤️2 br/2b New Modern Oceanfront Beach Condo

Beachfront home rentals with a pool

Washington 2 BR Suite.Modern and spacious MBJ

Townhouse in Montego Bay

2 BR townhouse, 24 hour security, gym, pool, ocean

Refined & Deluxe Oceanfront Condo in Montego Bay

Stunning beachfront 1 Bed/2 Bath - Resort Access

Rental unit in St.Bran's Burg

👉Cozy+Modern Beach apt w/Pool&Bar-WFH Montego Bay

Home in Montego Bay

Chatham Tropical Garden Hip Strip Hideaway

Three Bedroom Villa -Restaurant Nightlife Shop BCH

Cozy poolside getaway in The Lagoons Montego Bay

Private beachfront home rentals

Zach's Place

Serviced apartment in Montego Bay

16 Hip Strip Hotel Room Ocean View Beach Best Loct

Guest suite in Hanover Parish

C VIEW GATEHOUSE (ORCHARD GARDEN )

*A Hidden Gem at Resort in Montego Bay*

Comfy Apartment w/Ocean View, Pool & Beach Access

Sea Castles La Vue

Ocean View Terrace, Montego Bay Club Condo

Penthouse with Loft @Seacastles, Beach & Pool 207

Quick stats about beachfront rentals in Montego Bay

Total rentals.

100 properties

Nightly prices starting at

$50 before taxes and fees

Total number of reviews

6.9K reviews

Family-friendly rentals

30 properties are a good fit for families

Pet-friendly rentals

20 properties allow pets

Rentals with a pool

60 properties have a pool

Destinations to explore

• Kingston   Vacation rentals
• Ocho Rios   Vacation rentals
• Negril   Vacation rentals
• Portmore   Vacation rentals
• Mandeville   Vacation rentals
• Treasure Beach   Vacation rentals
• Discovery Bay   Vacation rentals
• Port Antonio   Vacation rentals
• Old Harbour   Vacation rentals
• Runaway Bay   Vacation rentals
• May Pen   Vacation rentals
• White House   Vacation rentals
• Beachfront rentals   Jamaica
• Kid-friendly rentals   Montego Bay
• Private suite rentals   Montego Bay
• Apartment rentals   Montego Bay
• Smoking-friendly rentals   Montego Bay
• Serviced apartment rentals   Montego Bay
• Pet-friendly rentals   Montego Bay
• Beach house rentals   Montego Bay
• Family-friendly rentals   Montego Bay
• Rentals with beach access   Montego Bay
• Villa rentals   Montego Bay
• Bed and breakfasts   Montego Bay
• Luxury rentals   Montego Bay
• House rentals   Montego Bay
• Rentals with pools   Montego Bay
• Rentals with a hot tub   Montego Bay
• Rentals with a washer and dryer   Montego Bay
• Rentals with breakfast   Montego Bay
• Fitness-friendly rentals   Montego Bay
• Condo rentals   Montego Bay
• Monthly Rentals   Montego Bay
• Waterfront rentals   Montego Bay
• Rentals with a fire pit   Montego Bay
• Rentals with a fireplace   Montego Bay
• Rentals with a patio   Montego Bay
• Townhouse rentals   Montego Bay
• Rentals with outdoor seating   Montego Bay
• Beachfront rentals   Ocho Rios
• Beachfront rentals   St. James Parish
• Yurt Rentals   United States
• Yurt Rentals   United Kingdom
• Castle Rentals   United States
• Houseboats   United States
• Holiday Caravans   United Kingdom
• Private Island Rentals   United States
• Farm Houses   United States
• Farm Cottages   United Kingdom
• Cabin Rentals   Australia
• Luxury Cabins   United Kingdom
• Luxury Cabins   United States
• Holiday Chalets   United Kingdom
• Cottage Rentals   United States
• Holiday Cottages   United Kingdom
• Mansion Rentals   United States
• Villa Rentals   United Kingdom
• Holiday Bungalows   United Kingdom
• Bungalow Rentals   United States
• Condo Rentals   United States
• Holiday Apartments   Australia
• Holiday Houses   United States
• Holiday Houses   United Kingdom
• Private Holiday Rentals   United Kingdom
• Big House Rentals   United States
• Big Cottages   Australia
• Large Villas   United Kingdom
• House Rentals with a Pool   United States
• Cabin Rentals with a Pool   United States
• Villas with a Pool   United Kingdom
• Apartments with a Hot Tub   United States
• Holiday Cottages with a Hot Tub   United Kingdom
• Beach Cabins   United States
• Beach Condos   United States
• Beachfront Rentals   United States
• Beach Houses   United Kingdom
• Beach Villas   United Kingdom
• Coastal Cottages   United Kingdom
• Pet-Friendly Vacation Rentals   United States
• Pet-Friendly Beach Rentals   United States
• Pet-Friendly Cabin Rentals   United States
• Dog-Friendly Cottages   United Kingdom
• Luxury Dog-Friendly Cottages   United Kingdom
• Things to do   Jamaica
• Nature and outdoors   Jamaica
• Things to do   St. James Parish
• Nature and outdoors   St. James Parish
• Things to do   Montego Bay
• Family travel hub   Tips and inspiration
• Family budget travel   Get there for less
• Vacation ideas for any budget   Make it special without making it spendy
• Travel Europe on a budget   How to take the kids to Europe for less
• Outdoor adventure   Explore nature with the family
• Bucket list national parks   Must-see parks for family travel
• Kid-friendly state parks   Check out these family-friendly hikes
• › Jamaica ›
• › St. James Parish ›
• › Montego Bay ›
• › Beachfront rentals