Title: Book the Best Islamorada LUXURY Hotels - Upscale Hotels in Islamorada, FL | Expedia.ca [Islamorada Travel Guide](https://expedia.ca/Islamorada.dx10768)[Hotels in Islamorada](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[Vacation Rentals in Islamorada](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[Flights to Islamorada](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[Things to do in Islamorada](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)[Islamorada Car Rentals](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[Islamorada Vacation Packages](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides) ![Islamorada featuring a sunset and general coastal views](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Islamorada, FL - ![](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 availability on Islamorada Luxury Hotels Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-12-26&endDate=2025-12-27&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-12-27&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Islamorada luxury hotels ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1276) "Fabulous waterfront, activities, and dining as well as the staff. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) David CA $380 CA $528 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/28233e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Accessible Room King Bed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/1b5ced17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/60b7c04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1266) "Friendly staff and beautiful property !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ron CA $293 CA $421 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/d0b4fd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/29680b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/42d378ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drop Anchor [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) Islamorada 8.8/10 Excellent (1002) "Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $192 CA $264 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Private beach, sun loungers, beach towels, scuba diving](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/c5948ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4dfe75fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/cb9f9f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) Islamorada 9.0/10 Wonderful (119) "Beautiful chilled out hotel" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Jacqueline CA $336 CA $469 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Water view](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d461c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Beds Water View](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d6bb28b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/371bf8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creekside Inn [](https://www.expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) Tavernier 8.0/10 Very good (1001) "Very comfortable stay Local dining walking distance many amenities close by Room was very clean and AC worked great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy CA $208 CA $234 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/12d77a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/43f5c138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1597) "The entire resort was wonderful." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mat CA $225 CA $331 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/7000000/6490000/6489600/6489579/8808dc70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6490000/6489600/6489579/3703fe63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed](https://images.trvl-media.com/lodging/7000000/6490000/6489600/6489579/085609f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6490000/6489600/6489579/5b9552f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Conch On Inn Motel [](https://www.expedia.ca/Tavernier-Hotels-Conch-On-Inn-Motel.h6489579.Hotel-Information) Indian Waterways 7.6/10 Good (488) "Overall great experience & owners were great. Only thing I would offer up is could use some new mattresses but everything else was more than expected! Would (or shouldsay will) stay again someday" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Tavernier-Hotels-Conch-On-Inn-Motel.h6489579.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/46d4fa27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w1009h683x7y0-80f60840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Jungles Suite](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w762h679x132y4-fc33a6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/eeb86e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Morada [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) Matecumbe 9.4/10 Exceptional (415) "always a pleasant stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert CA $599 CA $776 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9e08c794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/7c261d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/449b99c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher Inn Resort & Marina [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) Islamorada 8.2/10 Very good (1000) "We enjoyed are stay at Fisher Inn, room was clean and updated. The paddle board use was a nice perk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Magaly CA $221 CA $294 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/6ec44483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Islander Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1003) "The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $409 CA $553 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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=2026-01-09&endDate=2026-01-10®ionId=10768&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Islamorada ### Islamoradaand its attractions for luxury travelers Islamorada, nestled in the heart of the Florida Keys, offers a sumptuous blend of relaxation and adventure that will surely captivate luxury travellers. Begin your journey by exploring the stunning coral reefs at the John Pennekamp Coral Reef State Park, where you can indulge in private snorkelling or scuba diving tours amid vibrant marine life. For those seeking a taste of local culture, the Morada Way Arts and Cultural District is a delightful area to discover unique art galleries and artisanal shops, ideal for leisurely strolls and exquisite finds. You can also treat yourself to a gourmet dining experience at the renowned Chef Michael's, where fresh seafood is served in an elegant setting, showcasing the culinary excellence of the Keys. If you're inclined towards fishing, the world-class sport fishing charters available here promise an exhilarating day on the water, where you can reel in a trophy fish. Finally, unwind at the luxurious accommodations in the Upper Matecumbe Key area, where opulent resorts offer beachfront views, private balconies, and exceptional spa services, creating a perfect sanctuary for relaxation after a day of exploration. With attentive service and high-end amenities, your stay will be as memorable as the experiences that await you in this beautiful island paradise. ### Find the best luxury hotels and resorts in Islamorada For those seeking a luxurious escape in the stunning landscapes of Islamorada, Florida, these top hotels offer exceptional amenities and unparalleled comfort for discerning travellers. [**Chesapeake Beach Resort**](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) - **Why it's great for a luxury retreat:** Chesapeake Beach Resort is an idyllic choice for luxury travellers, a remarkable guest review rating of 9.2\. Guests can indulge in designer toiletries and enjoy the stunning resort views from their private balconies. The resort's private beach access ensures a tranquil seaside experience, complemented by attentive concierge services that cater to every need. - **Other amenities:** In addition to luxury offerings, guests can take advantage of features such as an outdoor pool with sun loungers, daily housekeeping services, and a kitchenette in select accommodations for added convenience. With boat tours available onsite, and nearby options for snorkeling and personal watercraft, adventure awaits just steps from the resort. The serene atmosphere is further enhanced by the beautiful beach towels provided for guests' convenience. - **Neighborhood:** Matecumbe - **Nearby attractions:** History of Diving Museum - 0.9 km, Theater of the Sea - 1.7 km, Windley Key Fossil Reef Geological State Park - 1.8 km [**Islander Resort**](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) - **Why it's great for a luxury retreat:** Islander Resort is a luxurious retreat that promises an exquisite stay, earning a stellar review rating of 9.2\. With beachside dining and champagne service, guests can indulge in the finer things while enjoying the resort's private beach access. The attentive concierge ensures that every aspect of the guest experience is catered to with sophistication and care. - **Other amenities:** The resort features an outdoor pool with poolside cabanas, premium bedding for ultimate comfort, and evening entertainment to enhance the guest experience. Guests can unwind with massages on the beach or explore the waters with onsite kayaking and snorkeling. With electric car charging stations and a variety of recreational facilities, the Islander Resort combines luxury with convenience and eco-friendliness. - **Neighborhood:** Matecumbe - **Nearby attractions:** Matecumbe United Methodist Church - 0.9 km, Keys History & Discovery Center - 0.1 km, Islamorada Brewery & Distillery - 0.8 km [**Cheeca Lodge & Spa**](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) - **Why it's great for a luxury retreat:** Cheeca Lodge & Spa stands out as a premier destination for luxury seekers, with an impressive guest review rating of 9.0\. This beachfront hotel offers exquisite amenities, including private hot tubs in select rooms and a stunning poolside bar, ensuring a lavish experience for all guests. The dedicated concierge is always on hand to assist with bespoke services, elevating the stay to new heights of indulgence. - **Other amenities:** Guests can enjoy a full-service spa with treatment rooms, an onsite golf course, and a variety of dining options, including couples dining experiences. The resort also features tennis courts and evening entertainment for those looking to unwind. With yoga classes available on the beach and complimentary bicycles to explore the area, Cheeca Lodge & Spa offers a perfect blend of relaxation and activity. - **Neighborhood:** Matecumbe - **Nearby attractions:** Matecumbe United Methodist Church - 0.1 km, Florida Keys Brewing Co. - 0.4 km, MoradaWay Arts & Cultural District - 0.6 km [**Amara Cay Resort**](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) - **Why it's great for a luxury retreat:** Amara Cay Resort is a luxurious escape with a charming review rating of 8.8, perfect for travellers seeking a blend of comfort and elegance. This stunning resort features beachfront dining and an inviting poolside bar, allowing guests to relax in style. With premium bedding and designer toiletries, each room is designed to provide a sumptuous experience for travelers. - **Other amenities:** The resort offers in-room massages and a variety of beach activities, ensuring guests can fully immerse themselves in the tranquil surroundings. With a focus on wellness, guests can participate in fitness classes and enjoy the beautiful garden areas. The hotel also includes convenient amenities like a kitchenette in select rooms, complimentary beach towels, and early check-in for added convenience. - **Neighborhood:** Matecumbe - **Nearby attractions:** Bud n' Mary's Dive Center - 0.3 km, Indian Key Historic State Park - 1.1 km, Hurricane Monument - 2.3 km [**La Siesta Resort & Villas**](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) - **Why it's great for a luxury retreat:** La Siesta Resort & Villas is a luxurious haven in Islamorada, an excellent review rating of 8.6\. Guests can revel in the resort's private beach access while enjoying premium bedding and designer toiletries in their accommodations. The attentive concierge is always available to enhance the stay with tailored recommendations and services. - **Other amenities:** The resort features a poolside bar, outdoor pool with sun loungers, and on-site dining options with ocean views. Guests can enjoy various activities such as kayaking and golfing at nearby locations. With self-parking and electric car charging stations available, La Siesta Resort & Villas ensures a comfortable and eco-conscious stay for all. - **Neighborhood:** Matecumbe - **Nearby attractions:** Bud n' Mary's Dive Center - 0.9 km, Indian Key Historic State Park - 0.5 km, Hurricane Monument - 1.7 km ## Top Islamorada Hotel Reviews ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :) " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "Beautiful chilled out hotel" [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg) ### Fisher Inn Resort & Marina 10/10 Excellent "We enjoyed are stay at Fisher Inn, room was clean and updated. The paddle board use was a nice perk! " [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special! " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Fabulous waterfront, activities, and dining as well as the staff. " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Pines & Palms Resort](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Great room great place. Very clean easy to get to wonderful staff " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 10/10 Excellent "While the facility has some age on it, everything was very clean and well kept." [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "Staff was wonderful! Location and amenities were great! Room was clean and comfortable!" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ## Frequently asked questions ### What are the top-rated luxury hotels in Islamorada? > The 5-star Cheeca Lodge & Spa, with a 9.2 rating, is distinguished by its private beach, on-site golf course, and tennis facilities. Guests frequently praise the friendly and amazing staff, as well as the beautiful and clean rooms. > > > The 4-star Amara Cay Resort, rated 8.8, offers a private beachfront restaurant and a poolside bar. Reviewers frequently highlight the friendly and amazing staff, and the beautiful location. > > > The 4-star Islander Resort, with a 9.2 rating, provides private beach access and beachfront dining. Customers particularly appreciate the beautiful and big pool, along with the great and amazing service. > > > The 4-star La Siesta Resort & Villas, rated 8.6, features designer toiletries and premium bedding. The staff are consistently praised as friendly and amazing, and the rooms as clean and big. ### Which area of Islamorada is best to stay in for luxury hotels? > This stretch of the Overseas Highway is where you'll find a collection of high-end resorts and private villas, many of which offer direct access to the ocean or bayside. These properties are typically set back from the main road, providing a sense of seclusion and tranquility. You'll often find amenities like private beaches, extensive tropical gardens, and multiple dining options on-site. > > > Couples looking for a romantic and exclusive getaway will find this area particularly appealing. The resorts here often cater to adults with features such as serene pool areas, spa services, and fine dining restaurants. Many offer water-based activities directly from their property, like guided fishing charters or paddleboarding, making it easy to enjoy the Florida Keys' natural beauty without venturing far. ### How much does a luxury hotel in Islamorada cost? ### Which luxury hotels in Islamorada are good for families? > The 5-star Cheeca Lodge & Spa, with a 9.2 rating, offers an array of amenities suitable for families, including an onsite golf course and tennis facilities. Guests frequently praise the friendly and amazing staff, as well as the beautiful and clean rooms. > > > The 4-star Amara Cay Resort, rated 8.8, provides a comfortable stay with its private beach access and beachfront restaurant. Reviewers often highlight the friendly staff, beautiful location, and clean, comfortable rooms. > > > Islander Resort, a 4-star property with a 9.2 rating, features a beautiful, large pool and evening entertainment. Customers consistently praise the friendly staff and the beautiful, clean rooms and amenities. > > > The 4-star La Siesta Resort & Villas, holding an 8.6 rating, offers spacious, clean rooms and excellent amenities. Its private beach access and resort structure are noted by guests, who often mention the friendly staff and great location. ### What are the best luxury hotels in Islamorada with a pool? > The 5-star Cheeca Lodge & Spa, with a 9.2 rating, provides a range of pool options, including private pools in some accommodations. Guests frequently praise the friendly and amazing staff, beautiful and clean rooms, and excellent service. The resort also boasts an onsite golf course and tennis facilities. > > > The 4-star Amara Cay Resort, rated 8.8, features a beautiful outdoor pool and a poolside bar. Reviewers often highlight the friendly and amazing staff, the beautiful location, and the comfortable and clean rooms. > > > Islander Resort, a 4-star establishment with a 9.2 rating, offers a beautiful and large pool. Customers consistently praise the friendly and great staff, the beautiful and clean rooms, and the great service. > > > [La Siesta Resort & Villas](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information), a 4-star property with an 8.6 rating, also provides an outdoor pool. Guests frequently mention the friendly staff, clean and spacious rooms, and the great location. ### Which luxury hotels in Islamorada are good for couples? > The 5-star Cheeca Lodge & Spa, with a 9.2 rating, is celebrated for its private beach, onsite golf course, and private outdoor hot tubs. Reviewers consistently praise the friendly and amazing staff, along with the beautiful and clean rooms. > > > The 4-star Islander Resort, also with a 9.2 rating, features a beachfront restaurant and champagne service, great for romantic evenings. Customers frequently comment on the beautiful and clean rooms, as well as the beautiful and large pool. > > > Amara Cay Resort, a 4-star property with an 8.8 rating, provides a private beach and a beachfront restaurant. Its suites and premium bedding are often noted by guests, who praise the friendly staff and the beautiful location. ### Are there any top luxury hotels near Indian Key Historic State Park? > The 5-star Cheeca Lodge & Spa, with a 9.2 rating, provides an array of upscale amenities including a private beach, an on-site golf course, and private outdoor hot tubs. Guests frequently praise its friendly and amazing staff, as well as the beautiful and clean rooms. > > > The 4-star Islander Resort, rated 9.2, features a beachfront restaurant and private beach access. Customers often highlight the beautiful and big pool, alongside the great and amazing service. > > > Amara Cay Resort, a 4-star property with an 8.8 rating, offers a private beach, beachfront restaurant, and amenities such as Egyptian cotton sheets. Reviewers consistently praise the friendly and amazing staff, and the beautiful location. ### What luxury activities and experiences are there in Islamorada? > Upper Matecumbe Key offers a selection of exclusive resorts with private beaches, marinas, and fine dining. You'll find properties here that provide amenities such as private villas, infinity pools, and personalised concierge services. Many of these establishments are located directly on the ocean side, offering stunning views and immediate access to water activities. > > > Couples looking for a romantic and indulgent escape will find Upper Matecumbe Key particularly appealing. Resorts in this area often specialise in creating memorable experiences, from private sunset cruises and bespoke fishing charters to spa treatments and gourmet meals prepared by private chefs. The focus is on relaxation and bespoke service, allowing couples to enjoy the natural beauty of the Keys in comfort. > > > Travellers seeking an active yet luxurious holiday will also appreciate this area. Many resorts offer private charters for deep-sea fishing, fly fishing, or snorkelling and diving excursions to the nearby coral reefs. ### How can I save on a luxury hotel in Islamorada with Expedia? ### Is it cheaper to book a luxury Islamorada hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Casino-Hotel.0-n6240961-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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