Title: Simpson Bay Vacation Rentals from CA $167: 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/523000/523262-kim-sha-beach.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Simpson Bay Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Simpson Bay ## Our top choices for Simpson Bay vacation rentals ![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) ![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) ![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) ### Hilton Vacation Club Royal Palm St. Maarten Simpson Bay 9.0/10 Wonderful (1118) "Most convenient hotel to stay, due to an array of shopping and dinning options near the property." CA $135 CA $178 total includes taxes & fees Sep 26 - Sep 27 [](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) ![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) ![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) ![Beautiful 2 Bedroom - 2 Bathroom | Living area](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/c9f7d443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hills Residence Simpson Bay 9.0/10 Wonderful (45) "Love the view first of all. Property was in a great location. " CA $206 CA $350 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Simpson-Bay-Hotels-69-Welfare-Rd.h98229949.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/49000000/48300000/48291900/48291846/f3cadb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![UNIT 4](https://images.trvl-media.com/lodging/49000000/48300000/48291900/48291846/e2e9ee7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![UNIT 6 | Beach/ocean view](https://images.trvl-media.com/lodging/49000000/48300000/48291900/48291846/9bcb60c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![UNIT 7 | Living area](https://images.trvl-media.com/lodging/49000000/48300000/48291900/48291846/17cce459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tradewinds at Simpson Bay Simpson Bay 9.4/10 Exceptional (28) "We enjoyed the stay to the fullest" [](https://www.expedia.ca/Simpson-Bay-Hotels-Tradewinds-At-Simpson-Bay.h48291846.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/53104e32.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) ![Suite, 3 Bedrooms | In-room dining](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/b5064e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simpson Bay Suites Simpson Bay 6.8/10 (123) "Highly recommended and friendly staff…" CA $149 CA $167 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Suites.h3991146.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/109000000/108780000/108773000/108772966/ccff8650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/109000000/108780000/108773000/108772966/7efa4810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108780000/108773000/108772966/f649f6fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108780000/108773000/108772966/56776d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath Simpson Bay 9.6/10 Exceptional (14) "I would stay here again" [](https://www.expedia.ca/Simpson-Bay-Hotels-Amazing-Waterfront-Views-New-2-Bed3-Bath.h108772966.Hotel-Information) ![Orchid | View from room](https://images.trvl-media.com/lodging/7000000/6560000/6558800/6558748/94627531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Jasmine | Private kitchen](https://images.trvl-media.com/lodging/7000000/6560000/6558800/6558748/8c8aaa87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Jasmine | Living area](https://images.trvl-media.com/lodging/7000000/6560000/6558800/6558748/9edc444a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sea Grape | Private kitchen](https://images.trvl-media.com/lodging/7000000/6560000/6558800/6558748/a04cf0b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Horny Toad Guesthouse Simpson Bay 9.4/10 Exceptional (53) "We like it being beachfront, wide verandas, spacious unit, host and staff were excellent!" [](https://www.expedia.ca/Simpson-Bay-Hotels-The-Horny-Toad-Guesthouse.h6558748.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/21000000/20350000/20347800/20347774/7a28a1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, an infinity pool](https://images.trvl-media.com/lodging/21000000/20350000/20347800/20347774/c83df0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20347800/20347774/6ffcf0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, music library, stereo](https://images.trvl-media.com/lodging/21000000/20350000/20347800/20347774/bc10fa9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean Pelican Key 9.8/10 Exceptional (77) "We chose the property based on proximity to family in the neighborhood and we could not have been happier with our selection. The private pool and access to beach was wonderful. The facility was beautiful and clean and suited our needs perfectly as the en suite bathroom for each bedroom was great." [](https://www.expedia.ca/Simpson-Bay-Hotels-One-Hundred-Million-Dollar-Yacht-On-Land-5-Star-Villa-With-Backup-Generator.h20347774.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42260000/42253400/42253370/3f018b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42260000/42253400/42253370/f44f9430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42260000/42253400/42253370/d191c2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/43000000/42260000/42253400/42253370/6e9ea0e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maho Beach House - Spacious 1 Bedroom Suite Maho, Sint Maarten 10/10 Exceptional (3) "I booked this very last minute for a short (2 night) stay. They were very quick to reply and confirm. It was a big place for a one bedroom on a island. It was very clean, well decorated and with a nice view of the ocean and planes coming in to land. The air-conditioning worked well and I was happy to find the bedroom had a ceiling fan. The location worked well for me, there was a charge for parking, but it is gated and guarded. When I had an issue logging onto the wifi I sent a msg via the VRBO... [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h42253370.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) ![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) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/20000000/19890000/19882600/19882516/dd5ae42a.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) ### 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! " CA $546 CA $717 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Simpson-Bay-Hotels-Sleeps-4-Ppl-Directly-ON-Beach.h19882516.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93090000/93080500/93080428/w1170h1560x0y486-fc347254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93090000/93080500/93080428/w1170h1560x0y486-d12f6205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/94000000/93090000/93080500/93080428/a835ae34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/94000000/93090000/93080500/93080428/03d62085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A curated two bedroom suite near Maho beach. Simpsonbay 10/10 Exceptional (2) "Great place. Nice and quite with beaches close " [](https://www.expedia.ca/Simpson-Bay-Hotels-Minimalistic-2-Bedroom-Apartment-Near-Maho-Beach.h93080428.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33660000/33655700/33655695/aab3065a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33660000/33655700/33655695/dc758a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33660000/33655700/33655695/12d0f116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33660000/33655700/33655695/w1024h803x0y13-e94d8def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront amazing 2 bedrooms Condo Beacon Hill 9.6/10 Exceptional (59) "Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!" [](https://www.expedia.ca/Simpson-Bay-Hotels-Oceanfront-Amazing-2-Bedrooms-Condo.h33655695.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100810000/100806800/100806785/w1663h1080x259y0-fbada392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100810000/100806800/100806785/w1639h1080x271y0-47a7a4d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100810000/100806800/100806785/w1015h1358x32y479-d0783ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100810000/100806800/100806785/w1673h1080x254y0-7f83d8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay Simpson Bay 10/10 Exceptional (11) "Will stay again. " [](https://www.expedia.ca/Simpson-Bay-Hotels-St-Martin-Atrium-1BR-Apartment.h100806785.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) ![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) ![On the beach](https://images.trvl-media.com/lodging/43000000/42280000/42277500/42277435/24107f8c.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) ### Caribbean Sea Studio next to The Morgan Resort Maho, Sint Maarten 8.0/10 Very good (1) CA $170 CA $265 total includes taxes & fees Sep 25 - Sep 26 [](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/115000000/114180000/114178000/114177922/1b19fc0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114180000/114178000/114177922/cc92cc12.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) ![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) ### 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" CA $347 CA $672 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Simpson-Bay-Hotels-Sunny-Days-At-Simpson-Bay-Yacht-Club.h114177922.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33950000/33940400/33940329/3f272074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33950000/33940400/33940329/19bf9614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33950000/33940400/33940329/ba242125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33950000/33940400/33940329/c0fc3fcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchor House - Direct Oceanfront - Luxury & Modern Style Cupecoy 10/10 Exceptional (146) "The property itself was beautiful and the view was or if this world! Access to nightlife, beaches, restaurants was perfect. So quiet and peaceful. We were so sad to leave!" [](https://www.expedia.ca/Simpson-Bay-Hotels-Anchor-House-Direct-Oceanfront-Luxury-Modern-Style.h33940329.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/28000000/27170000/27166600/27166586/3b14c2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free minibar, in-room safe, desk](https://images.trvl-media.com/lodging/28000000/27170000/27166600/27166586/13c88d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27170000/27166600/27166586/c8741fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27170000/27166600/27166586/127b3628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top of the art penthouse on the beach - 4000 sq. ft of luxury Simpson Bay 10/10 Exceptional (76) "Amazing property Fantastic location Incredible views Great getaway " [](https://www.expedia.ca/Simpson-Bay-Hotels-Top-Of-The-Art-Penthouse-On-The-Beach-4000-Sq-Ft-Of-Luxury.h27166586.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33240000/33232700/33232623/11658d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33240000/33232700/33232623/w2032h1190x0y0-99b29968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33240000/33232700/33232623/cde3d624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33240000/33232700/33232623/76db7929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront amazing 2 BR Villa - 2 min from the beach Beacon Hill 9.4/10 Exceptional (96) "Good stay nice place property is comfortable, quiet, private, easily accessible, amenities worked well, kitchen very well equipment. Enjoyed my stay so did my group." [](https://www.expedia.ca/Simpson-Bay-Hotels-Oceanfront-Amazing-2-Bedrooms-Condo.h33232623.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33490000/33488800/33488728/453dc401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, music library, stereo](https://images.trvl-media.com/lodging/34000000/33490000/33488800/33488728/5d2c3701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33488800/33488728/be807c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33490000/33488800/33488728/50831b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea Pelican Key 9.6/10 Exceptional (48) "The house and view are as amazing as the pictures show. Kitchen is well equipped. Plenty of bath towels and beach towels. Supplies are well equipped as well (detergent, paper towels, toilet paper, etc.). Peaches and Michael are both very quick to respond. Would stay here again and recommend to friends. Great location, close to many great restaurants and activities. One of the nicest personal rentals we have ever stayed at." [](https://www.expedia.ca/Simpson-Bay-Hotels-Pelican-Key-Private-Luxury-Villa-With-Panoramic-View-Of-The-Caribbean-Sea.h33488728.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107890000/107880500/107880482/70f06043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 bedroom with pool in Simpson Bay - GENERATOR Sint Maarten 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." CA $159 CA $308 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Simpson-Bay-Hotels-1-Bedroom-With-Pool-In-Simpson-Bay-GENERATOR.h107880482.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/89000000/88930000/88927000/88926902/c847d8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/89000000/88930000/88927000/88926902/0277ef92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/89000000/88930000/88927000/88926902/b4593366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88930000/88927000/88926902/b03420e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pirates Booty - Beach Bar Studio next to The Morgan Resort Simpson Bay 8.6/10 Excellent (4) "Welcoming love the area we will be coming back thank you so much " CA $188 CA $293 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Simpson-Bay-Hotels-Pirates-Booty-Beach-Bar-Studio-At-Morgan-Resort.h88926902.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=2025-10-08&endDate=2025-10-09®ionId=8941&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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 ![The Atrium Beach Resort and Spa, an Ascend Collection Resort](//images.trvl-media.com/lodging/2000000/1750000/1746400/1746391/0308f8df_y.jpg) ### The Atrium Beach Resort and Spa, an Ascend Collection Resort 10/10 Excellent "Convenient. Very close to the airport lots of restaurants around " [](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](//images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg) ### Hilton Vacation Club Flamingo Beach St. Maarten 10/10 Excellent "Very quiet and clean. A lot of good places to eat nearby. On the beach." [](https://expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.Hotel-Information) ![Simpson Bay Resort, Marina & Spa](//images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg) ### Simpson Bay Resort, Marina & Spa 10/10 Excellent "This hotel out of the two was 100% the best! It was beautiful, comfortable, staff was excellent and the beach was great! Can’t wait to come back!" [](https://expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Resort.h1256868.Hotel-Information) ![The Villas at Simpson Bay Resort](//images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg) ### The Villas at Simpson Bay Resort 10/10 Excellent "I love this place! " [](https://expedia.ca/Simpson-Bay-Hotels-The-Villas-At-Simpson-Bay-Beach-Resort-And-Marina.h4553784.Hotel-Information) ![The Morgan Resort Spa Village](//images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg) ### The Morgan Resort Spa Village 10/10 Excellent "Close to everything " [](https://expedia.ca/Simpson-Bay-Hotels-The-Morgan-Resort-Spa-Village.h17524915.Hotel-Information) ![Azure Hotel and Art Studio](//images.trvl-media.com/lodging/6000000/5230000/5225100/5225071/93d281c5_y.jpg) ### Azure Hotel and Art Studio 10/10 Excellent "Michael was really great. Place was spotless and we'll located. Highly recommend. " [](https://expedia.ca/Simpson-Bay-Hotels-Azure-Hotel-And-Art-Studio.h5225071.Hotel-Information) ![Baker's Suites](//images.trvl-media.com/lodging/8000000/7750000/7741800/7741757/7b7d5aaa_y.jpg) ### Baker's Suites 10/10 Excellent "The place was clean and the staff are friendly. Public transportation in walking distance and lots restaurants in the area. Its an ideal location. " [](https://expedia.ca/Simpson-Bay-Hotels-Bakers-Suites.h7741757.Hotel-Information) ![Hilton Vacation Club Royal Palm St. Maarten](//images.trvl-media.com/lodging/1000000/810000/807900/807815/ddd10394_y.jpg) ### Hilton Vacation Club Royal Palm St. Maarten 10/10 Excellent "I will try to stay at this magnificent place every time I make it to Sint Maarten" [](https://expedia.ca/Simpson-Bay-Hotels-Royal-Palm-Beach-Resort-By-Diamond-Resorts.h807815.Hotel-Information) ![La Vista Hotel](//images.trvl-media.com/lodging/114000000/113160000/113158300/113158235/cde971ba_y.jpg) ### La Vista Hotel 10/10 Excellent "Great people, great time, there if you want and not if you want. " [](https://expedia.ca/Simpson-Bay-Hotels-La-Vista-Hotel.h113158235.Hotel-Information) ## Find out more about Simpson Bay **Everything you need to know about** **Simpson Bay** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Simpson Bay vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay vacation rentals we have selected for you start as low as CA $167 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Simpson Bay rentals** At Expedia, we put the best Simpson Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## 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 [Caribbean Sea Studio next to The Morgan Resort](https://www.expedia.ca/Simpson-Bay-Hotels-Caribbean-Sea-Studio-Next-To-The-Morgan-Resort.h42277435.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 39 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? > Flamingo Beach and Simpson Bay Beach are a couple of lovely local spots to get outside and enjoy nature. Kim Sha Beach and Hollywood Casino are other places to visit while you're in town. ### 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 - [St. Thomas All Inclusive Resorts and Hotels](https://expedia.ca/St-Thomas-Hotels-All-Inclusive-Hotel.0-0-d6140138-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Best Hotels in Philipsburg](https://expedia.ca/Philipsburg-Hotels.d3331.Travel-Guide-Hotels) - [Best Hotels in St. George's](https://expedia.ca/St-Georges-Hotels.d10788.Travel-Guide-Hotels) - [Best Hotels in St. Barthelemy](https://expedia.ca/St-Barthelemy-Hotels.d6140949.Travel-Guide-Hotels) - [Best Hotels in St. Thomas](https://expedia.ca/St-Thomas-Hotels.d6140138.Travel-Guide-Hotels) Flights - [Flights to STT](https://expedia.ca/Cheap-Flights-To-St-Thomas.d6140138.Travel-Guide-Flights) - [Flights to SJU](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 - [Flight and Hotel St. John](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) - [Flight and Hotel St. Barthelemy](https://expedia.ca/St-Barthelemy.d6140949.Destination-Travel-Guides) - [Flight and Hotel St. Thomas](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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)