Title: Simpson Bay Vacation Rentals from CA $192: Short-Term Rentals for 2025 | Expedia.ca [Simpson Bay Travel Guide](https://expedia.ca/Simpson-Bay.dx8941)[Hotels in Simpson Bay](https://expedia.ca/Simpson-Bay-Hotels.d8941.Travel-Guide-Hotels)[Flights to Simpson Bay](https://expedia.ca/Cheap-Flights-To-Simpson-Bay.d8941.Travel-Guide-Flights)[Things to do in Simpson Bay](https://expedia.ca/Things-To-Do-In-Simpson-Bay.d8941.Travel-Guide-Activities)[Simpson Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Simpson-Bay.d8941.Car-Rental-Guide)[Simpson Bay Vacation Packages](https://expedia.ca/Simpson-Bay.d8941.Destination-Travel-Guides) ![Kim Sha Beach showing general coastal views and a coastal town](https://images.trvl-media.com/place/6079645/4e72a445-56d2-45d3-858f-efcb71e137a2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Simpson Bay Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Nov 25 - Nov 26](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-11-25&endDate=2025-11-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 26 - Nov 27](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-11-26&endDate=2025-11-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Simpson Bay ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/ddd10394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/d586056b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/dfa126bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/ace5cf51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Royal Palm St. Maarten Simpson Bay 9.0/10 Wonderful (1155) "Beautiful vacation " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) alonzo CA $192 CA $238 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Simpson-Bay-Hotels-Royal-Palm-Beach-Resort-By-Diamond-Resorts.h807815.Hotel-Information) ![Amazing Top Floor Apartment | Balcony](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/e557289d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Apartment](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/9021be44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 outdoor pools](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/ae36c6fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment | Living area](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/5be85f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hills Residence Simpson Bay 8.8/10 Excellent (50) "This apartment was nice, clean, modern, walking distance to restaurants and shops. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lionel CA $231 CA $385 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Simpson-Bay-Hotels-69-Welfare-Rd.h98229949.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/108000000/107890000/107880500/107880482/18b10283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107890000/107880500/107880482/86847ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107890000/107880500/107880482/b9761987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107890000/107880500/107880482/5632da1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 bedroom with pool in Simpson Bay - GENERATOR (1-3B) Simpson Bay 10/10 Exceptional (1) "Communication with the host was very easy. The location is outstanding and the facility has every amenity. You can imagine. I highly recommend this property and can’t wait to visit again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard S. CA $203 CA $362 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Simpson-Bay-Hotels-1-Bedroom-With-Pool-In-Simpson-Bay-GENERATOR.h107880482.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/e9e59cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/edee56dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/b00cd486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/53104e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simpson Bay Suites Simpson Bay 6.8/10 (125) "No issues. Staff were very welcoming and accommodating. Was a pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmain CA $171 CA $192 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Suites.h3991146.Hotel-Information) ![Smart TV, stereo, offices](https://images.trvl-media.com/lodging/106000000/105950000/105942900/105942898/3a114358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105950000/105942900/105942898/94c252a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105950000/105942900/105942898/2d9d6494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105950000/105942900/105942898/4dd7624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marina Views in the Heart of Simpson Bay Simpson Bay 10/10 Exceptional (1) "We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trish S. CA $251 CA $509 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Simpson-Bay-Hotels-Marina-Views-In-The-Heart-Of-Simpson-Bay.h105942898.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42260000/42251500/42251454/fb169fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/43000000/42260000/42251500/42251454/7dfde8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/43000000/42260000/42251500/42251454/c5b0fdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, music library](https://images.trvl-media.com/lodging/43000000/42260000/42251500/42251454/e54c7c55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maho Beach House: Sunset Suite, 1-Bedroom Maho 10/10 Exceptional (1) "We had a great stay. Noah and Dwayne were great to work with. They were quick to respond to any questions we had or help we needed. We enjoyed out daily walks and spent time enjoying 3 different beaches within walking distance as well great places to eat, drink and enjoy time in the sun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn A. CA $310 CA $437 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Simpson-Bay-Hotels-Aquamarine-Guest-Suite.h42251454.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42270000/42270000/42269914/bf5161cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/43000000/42270000/42270000/42269914/e8a6f575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/43000000/42270000/42270000/42269914/282ee9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, electric kettle, toaster](https://images.trvl-media.com/lodging/43000000/42270000/42270000/42269914/0d45f766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maho Beach House: Studio Getaway, Oceanfront Vibe Maho, Sint Maarten 10/10 Exceptional (2) "Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen M. CA $288 CA $405 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h42269914.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119940000/119939900/119939847/ba7e411f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119940000/119939900/119939847/3d2780e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119940000/119939900/119939847/c37a97bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119940000/119939900/119939847/521be235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanview Escape in Sint Maarten Pelican Key CA $243 CA $707 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Simpson-Bay-Hotels-Oceanview-Escape-In-Sint-Maarten.h119939847.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/115000000/114180000/114178000/114177922/1b19fc0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114180000/114178000/114177922/w1815h2420x0y0-d7ab5765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114180000/114178000/114177922/77bf992b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114180000/114178000/114177922/18507f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunny Days at Simpson Bay Yacht Club Simpson Bay 10/10 Exceptional (2) "This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JEROME J. CA $468 CA $812 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Simpson-Bay-Hotels-Sunny-Days-At-Simpson-Bay-Yacht-Club.h114177922.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42280000/42277500/42277435/494af61a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42280000/42277500/42277435/59949753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42280000/42277500/42277435/e43c39c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, an infinity pool](https://images.trvl-media.com/lodging/43000000/42280000/42277500/42277435/e4c0da19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribbean Sea Studio next to The Morgan Resort Maho, Sint Maarten 8.0/10 Very good (1) CA $229 CA $334 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Simpson-Bay-Hotels-Caribbean-Sea-Studio-Next-To-The-Morgan-Resort.h42277435.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185523/aca000c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185523/8fef4cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185523/6aff326a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185523/5a6dd6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A116 - Immersive Simpson Bay Lagoon View Sint Maarten [](https://www.expedia.ca/Simpson-Bay-Hotels-A116-Immersive-Simpson-Bay-Lagoon-View.h97185523.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/117000000/116770000/116762200/116762134/b429b3a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116770000/116762200/116762134/5d003d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116770000/116762200/116762134/0368c322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116770000/116762200/116762134/680e8a8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### C323 – Elegant apartment with glass wall Sint Maarten CA $250 CA $429 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Simpson-Bay-Hotels-C323-Sleek-1-Bedroom-With-Panoramic-Glass-Wall.h116762134.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/122000000/121210000/121203200/121203153/602b6d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/122000000/121210000/121203200/121203153/6fd2a7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121210000/121203200/121203153/7d9de472.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121210000/121203200/121203153/37bf9376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A117 - Lovely 2 Bedroom with Lagoon View Sint Maarten CA $316 CA $485 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Simpson-Bay-Hotels-A117-Lovely-2-Bedroom-With-Lagoon-View.h121203153.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112240000/112239400/112239398/193c03ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112240000/112239400/112239398/d59b43c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112240000/112239400/112239398/37199ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112240000/112239400/112239398/c1f266d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maho Beach House: Elegant 1-Bedroom, Beach Level Simpson Bay CA $303 CA $413 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Simpson-Bay-Hotels-Maho-Beach-House-Elegant-1-Bedroom.h112239398.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19882600/19882516/1168416f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19890000/19882600/19882516/45bfb4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19890000/19882600/19882516/b9d3faa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/20000000/19890000/19882600/19882516/105770b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turquoise paradise, directly ON beach, gated w underground parking! Simpson Bay 9.8/10 Exceptional (20) "This is the perfect place to stay location wise and with the beach views! Also there is a/c in each room which is super nice! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel S. CA $557 CA $732 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Simpson-Bay-Hotels-Sleeps-4-Ppl-Directly-ON-Beach.h19882516.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/113000000/112880000/112876600/112876519/8b88d0ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/113000000/112880000/112876600/112876519/f614e6cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112880000/112876600/112876519/159c0da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112880000/112876600/112876519/c5f09369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beacon Hill Hideaway: Luxury Condo in Simpson Bay Simpson Bay CA $403 CA $811 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Simpson-Bay-Hotels-Beacon-Hill-Hideaway-Luxury-Condo-In-Simpson-Bay.h112876519.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185525/2e970242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185525/4ac991a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185525/9f6ac48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/98000000/97190000/97185600/97185525/5a727d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A101 - Outstanding Lagoon View & Garden Sint Maarten CA $276 CA $460 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Simpson-Bay-Hotels-A101-Outstanding-Lagoon-View-Garden.h97185525.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/102000000/101840000/101834600/101834553/a0d1b7c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/102000000/101840000/101834600/101834553/811e8732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101840000/101834600/101834553/00c1f83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/102000000/101840000/101834600/101834553/cb30aed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A111 - Condo with amazing view Sint Maarten CA $398 CA $608 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Simpson-Bay-Hotels-A111-Condo-With-Amazing-View.h101834553.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/98000000/97190000/97182500/97182460/3e017dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97190000/97182500/97182460/44115ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97190000/97182500/97182460/a703bef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97190000/97182500/97182460/54dacecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A114 - Beautiful Lagoon View & Balcony Sint Maarten [](https://www.expedia.ca/Simpson-Bay-Hotels-A114-Beautiful-Lagoon-View-Balcony.h97182460.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/a76595e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, offices, printers](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/c52cbfb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/328ffe43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, offices, printers](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/a0715f8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3BR Villa w Private Pool in Pelican Key Pelican Key CA $444 CA $1,002 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Simpson-Bay-Hotels-Charming-3BR-Villa-W-Private-Pool-In-Pelican-Key.h113245474.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11®ionId=8941&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=VR_BF_PROMO_8941) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSimpson-Bay-Vacation-Rentals.d8941.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSimpson-Bay-Vacation-Rentals.d8941.Travel-Guide-VacationRentals) ## Top Simpson Bay Hotel Reviews ![Hilton Vacation Club Royal Palm St. Maarten](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/ddd10394_y.jpg) ### Hilton Vacation Club Royal Palm St. Maarten 10/10 Excellent "Lovely" [](https://expedia.ca/Simpson-Bay-Hotels-Royal-Palm-Beach-Resort-By-Diamond-Resorts.h807815.Hotel-Information) ![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg) ### The Villas at Simpson Bay Resort 10/10 Excellent "Large comfortable room. Amazing beach!" [](https://expedia.ca/Simpson-Bay-Hotels-The-Villas-At-Simpson-Bay-Beach-Resort-And-Marina.h4553784.Hotel-Information) ![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg) ### The Morgan Resort Spa Village 10/10 Excellent "Great experience " [](https://expedia.ca/Simpson-Bay-Hotels-The-Morgan-Resort-Spa-Village.h17524915.Hotel-Information) ![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg) ### Simpson Bay Resort, Marina & Spa 10/10 Excellent "Nice resort clean close to the water nice staff" [](https://expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Resort.h1256868.Hotel-Information) ![The Atrium Beach Resort and Spa, an Ascend Collection Resort](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746391/3e2b89c6_y.jpg) ### The Atrium Beach Resort and Spa, an Ascend Collection Resort 10/10 Excellent "I always enjoy being at the Atrium in St Maaten" [](https://expedia.ca/Simpson-Bay-Hotels-Atrium-Beach-Resort-And-Spa-St-Maarten-A-Ramada-By-Wyndham.h1746391.Hotel-Information) ![Hilton Vacation Club Flamingo Beach St. Maarten](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg) ### Hilton Vacation Club Flamingo Beach St. Maarten 10/10 Excellent "Everything was perfect!" [](https://expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.Hotel-Information) ![Commodore Suites](https://images.trvl-media.com/lodging/16000000/15090000/15082100/15082011/acd4d986_y.jpg) ### Commodore Suites 10/10 Excellent "Nice and close to Tap n Still" [](https://expedia.ca/Simpson-Bay-Hotels-Commodore-Suites.h15082011.Hotel-Information) ![Tradewinds at Simpson Bay](https://images.trvl-media.com/lodging/49000000/48300000/48291900/48291846/f3cadb3a_y.jpg) ### Tradewinds at Simpson Bay 10/10 Excellent "This place is amazing. Great price. Super helpful and flexible owner and staff. They truly did everything to help and make my stay perfect. The room was clean. The bed was very comfortable. There's beautiful sunset view from this property. Great seafood restaurant next door. I'll definitely be back. 10 out of 10" [](https://expedia.ca/Simpson-Bay-Hotels-Tradewinds-At-Simpson-Bay.h48291846.Hotel-Information) ![Azure Hotel and Art Studio](https://images.trvl-media.com/lodging/6000000/5230000/5225100/5225071/93d281c5_y.jpg) ### Azure Hotel and Art Studio 10/10 Excellent "Very pleasant staff, clean and right on the beach. Had a wonderful stay" [](https://expedia.ca/Simpson-Bay-Hotels-Azure-Hotel-And-Art-Studio.h5225071.Hotel-Information) ## Find out more about Simpson Bay You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Simpson Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Simpson Bay ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Resorts in Simpson Bay](https://expedia.ca/Simpson-Bay-Resort-Hotels.d8941-aaResortHotels.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find a vacation rental in Simpson Bay? > Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars. ### What are some of the best vacation home rentals that Simpson Bay has to offer? > [Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool](https://www.expedia.ca/Simpson-Bay-Hotels-Amazing-7-Bedroom-5-Bath-Villa-Beachfront-Private-Pool.h89641287.Hotel-Information) : Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Simpson Bay are [White Sands Retreat - Beachside at Beacon Hill](https://www.expedia.ca/Simpson-Bay-Hotels-White-Sands-Retreat-Beachside-At-Beacon-Hill.h34334529.Hotel-Information) and [Charming 3BR Villa w Private Pool in Pelican Key](https://www.expedia.ca/Simpson-Bay-Hotels-Charming-3BR-Villa-W-Private-Pool-In-Pelican-Key.h113245474.Hotel-Information). ### How many vacation rentals are there in Simpson Bay? > With 37 Expedia vacation rentals, you're sure to find just the right place for your Simpson Bay stay. ### What’s there to see and do in Simpson Bay? > Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find popular places like Maho Beach and Orient Bay Beach. ### What’s a vacation rental in Simpson Bay like? > A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families. ### Expedia's Latest Trends Hotels - [All Inclusive Resorts and Hotels in St. Thomas](https://expedia.ca/St-Thomas-Hotels-All-Inclusive-Hotel.0-0-d6140138-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Hotels in Philipsburg](https://expedia.ca/Philipsburg-Hotels.d3331.Travel-Guide-Hotels) - [Hotels in St. George's](https://expedia.ca/St-Georges-Hotels.d10788.Travel-Guide-Hotels) - [Hotels in St. Barthelemy](https://expedia.ca/St-Barthelemy-Hotels.d6140949.Travel-Guide-Hotels) - [Hotels in St. Thomas](https://expedia.ca/St-Thomas-Hotels.d6140138.Travel-Guide-Hotels) Flights - [Flights to St. Thomas](https://expedia.ca/Cheap-Flights-To-St-Thomas.d6140138.Travel-Guide-Flights) - [Flights to Florida](https://expedia.ca/Cheap-Flights-To-Florida.d6231778.Travel-Guide-Flights) Cars - [Car rentals in Philipsburg](https://expedia.ca/Car-Rentals-In-Philipsburg.d3331.Car-Rental-Guide) - [Car rental Simpson Bay Airport (SXM)](https://expedia.ca/Car-Rentals-In-Princess-Juliana-Intl.d5068883.Car-Rental-Guide) Activities - [Things to do in Castries](https://expedia.ca/Things-To-Do-In-Castries.d3209.Travel-Guide-Activities) - [Things to do in Oranjestad](https://expedia.ca/Things-To-Do-In-Oranjestad.d450.Travel-Guide-Activities) - [Things to do in St. George's](https://expedia.ca/Things-To-Do-In-St-Georges.d10788.Travel-Guide-Activities) - [Things to do in Vieux Fort](https://expedia.ca/Things-To-Do-In-Vieux-Fort.d178203.Travel-Guide-Activities) - [Things to do in Oyster Pond](https://expedia.ca/Things-To-Do-In-Oyster-Pond.d6025558.Travel-Guide-Activities) - [Things to do in St. Thomas](https://expedia.ca/Things-To-Do-In-St-Thomas.d6140138.Travel-Guide-Activities) - [Things to do in Philipsburg](https://expedia.ca/Things-To-Do-In-Philipsburg.d3331.Travel-Guide-Activities) - [Things to do in Orient Bay](https://expedia.ca/Things-To-Do-In-Orient-Bay.d602894.Travel-Guide-Activities) Packages - [St. John Vacations](https://expedia.ca/St-John.d601376.Destination-Travel-Guides) - [Kim Sha Beach](https://expedia.ca/Kim-Sha-Beach-Simpson-Bay.d6079645.Vacation-Attraction) - [St. Thomas All-inclusive Vacation Packages](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations/6140138/St-Thomas) - [St. Barthelemy Vacations](https://expedia.ca/St-Barthelemy.d6140949.Destination-Travel-Guides) - [St. Thomas Vacations](https://expedia.ca/St-Thomas.d6140138.Destination-Travel-Guides) General - [Visit Philipsburg](https://expedia.ca/Philipsburg.dx3331) - [Visit Gros Islet](https://expedia.ca/Gros-Islet.dx11648) - [Visit Basseterre](https://expedia.ca/Basseterre.dx3183) - [Visit St. John](https://expedia.ca/St-John.dx601376) - [Visit St. Thomas](https://expedia.ca/St-Thomas.dx6140138) - [Visit Oranjestad](https://expedia.ca/Oranjestad.dx450) - [Visit Willemstad](https://expedia.ca/Willemstad.dx937) - [Visit Soufrière](https://expedia.ca/Soufriere.dx9521) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)