Title: Upper Matecumbe Key Condominium Resort Rental from CA $231 | Expedia.ca

[Upper Matecumbe Key Travel Guide](https://expedia.ca/Upper-Matecumbe-Key.dx553248635975749648)[Hotels in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Vacation Rentals in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[Flights to Upper Matecumbe Key](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Upper Matecumbe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)[Upper Matecumbe Key Vacation Packages](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides)

![Florida Keys Brewing Co. showing signage](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find and Compare Upper Matecumbe Key Condo Resort Rentals

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## Check prices for these dates

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Upper Matecumbe Key

![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)

![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)

![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)

### Chesapeake Beach Resort

[](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

9.2/10

Wonderful

(1605)

"The entire resort was wonderful."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Mat

CA $246

CA $354 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 2 Queen Beds, Kitchenette, Bay View](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/c0d44f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/ac9bc991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Jolla Resort

[](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information)

9.0/10

Wonderful

(1005)

"Great stay. Friendly staff, great accommodations, very nice complex. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shela

CA $171

CA $231 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.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)

![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)

![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/3ea0faf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Islander Resort

[](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information)

9.2/10

Wonderful

(1006)

"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)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98496c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Cottage | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/7a0bffa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

8.8/10

Excellent

(600)

"Property was nice and easy to navigate, ocean view room was extra nice to have!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa

CA $190

CA $284 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.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)

![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)

![One Bedroom Oceanfront Suite King](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2f598fe7.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)

### Resort in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

8.8/10

Excellent

(1270)

"Friendly staff and beautiful property !"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ron

CA $293

CA $430 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

![Outdoor pool, free cabanas](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/92298919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/0fad4f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Double Beds, Kitchenette](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/4c5cb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Inn

[](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information)

9.4/10

Exceptional

(1003)

"Clean, spacious, updated room. Great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly

CA $213

CA $255 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information)

![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)

![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.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)

### Resort in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

9.2/10

Wonderful

(1279)

"Fabulous waterfront, activities, and dining as well as the staff. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

David

CA $352

CA $497 total

includes taxes & fees

Jan 29 - Jan 30, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

![Dock](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/8f06ee9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach towels, kayaking](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/8952c233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/00476fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hadley Resort and Marina

[](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information)

7.6/10

Good

(1006)

"Patio nice , pool area good , good walk to things to do ,dive museum , brewery, shopping. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John

CA $203

CA $273 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach/ocean view](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a11bb47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, Multiple Beds (Casa de Coco) | Dining room](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/9c557f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/7578de06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Resort in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information)

8.8/10

Excellent

(1002)

"Great accommodations, very peaceful setting "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan

CA $245

CA $376 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information)

![Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/b1df7837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach umbrellas, beach towels](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/658c83a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/d3f952a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sands of Islamorada

[](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information)

8.8/10

Excellent

(393)

"The rooms were recently remodeled and very nice. People are really nice."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tammie

CA $247

CA $297 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45b47efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/a571015b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45deddf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pines & Palms Resort

[](https://www.expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information)

9.2/10

Wonderful

(1001)

"Staff are excellent, resort has been recently upgraded. Best describe his quaint, comfortable and cozy."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

scott

CA $319

CA $434 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/8ad54011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/641fc549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Villas by Islander Resort

[](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information)

8.8/10

Excellent

(404)

"Beautiful stay!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lakyne

CA $394

CA $535 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information)

![2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fa0090c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

9.8/10

Exceptional

(70)

"Great for family vacation with kids. love it"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dixania

CA $833

CA $1,012 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![Manatee Suite | Terrace/patio](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/fb67a862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shangri-La Suite | Terrace/patio](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/58abb15a.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)

![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)

### Casa Morada

[](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information)

9.4/10

Exceptional

(416)

"always a pleasant stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

robert

CA $560

CA $725 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w792h683x116y0-40905cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w585h683x219y0-67ce19b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w865h663x80y0-59e3e4fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/118000000/117530000/117523100/117523098/w1009h683x7y0-57cf914a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Peaceful-Garden-King-Suite-Islamorada-Gem-Gumbo-Limbo-Suite.h117523098.Hotel-Information)

CA $1,367

CA $1,732 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Peaceful-Garden-King-Suite-Islamorada-Gem-Gumbo-Limbo-Suite.h117523098.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117500000/117496200/117496122/w970h683x27y0-6cabc910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/118000000/117500000/117496200/117496122/w967h683x28y0-e8ad915f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117500000/117496200/117496122/w969h683x27y0-d76a6ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/118000000/117500000/117496200/117496122/w453h683x285y0-a8bb47c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Romantic-Suite-With-Jacuzzi-Garden-Oasis-Islamorada-Jungles-Suite-Room.h117496122.Hotel-Information)

CA $1,367

CA $1,732 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Romantic-Suite-With-Jacuzzi-Garden-Oasis-Islamorada-Jungles-Suite-Room.h117496122.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/w792h683x116y0-b196f56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/w796h683x114y0-c357f0e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/w865h663x80y0-99d56dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/078e3a39_edited_78aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Serene-Moon-Suite-W-Jacuzzi-Garden-View-Islamorada-Moon-Suite.h117525589.Hotel-Information)

CA $2,051

CA $2,598 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Serene-Moon-Suite-W-Jacuzzi-Garden-View-Islamorada-Moon-Suite.h117525589.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/w792h683x116y0-c9518e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/w1009h683x7y0-686fbd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/w865h663x80y0-1168dbdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/fb8ef6dd_edited_a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Oceanfront-Manatee-Suite-W-Private-Patio-Islamorada-Manatee-Suite.h117551960.Hotel-Information)

CA $2,214

CA $2,805 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Oceanfront-Manatee-Suite-W-Private-Patio-Islamorada-Manatee-Suite.h117551960.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w792h683x116y0-8979e8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w1009h683x7y0-0c5c0daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/cd5d8567_edited_3543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w962h680x31y3-3a73e5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Terrace-Florida-Bay-View-Suite-Islamorada-Shangri-La-Suite.h117551749.Hotel-Information)

CA $2,226

CA $2,821 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Terrace-Florida-Bay-View-Suite-Islamorada-Shangri-La-Suite.h117551749.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/118000000/117540000/117537900/117537821/w792h683x116y0-b4568acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117540000/117537900/117537821/w585h683x219y0-ac376e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117540000/117537900/117537821/w865h663x80y0-247070ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/118000000/117540000/117537900/117537821/w1009h683x7y0-9aea9b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Matecumbe

[](https://www.expedia.ca/Islamorada-Hotels-Private-Hideaway-W-Balcony-Lush-Views-Islamorada-Hideaway-Suite.h117537821.Hotel-Information)

CA $2,596

CA $3,290 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Islamorada-Hotels-Private-Hideaway-W-Balcony-Lush-Views-Islamorada-Hideaway-Suite.h117537821.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=2026-01-12&endDate=2026-01-13&regionId=553248635975749648&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America&regionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=HOUSE_BOAT)

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## Top Upper Matecumbe Key Hotel Reviews

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg)

### Hawks Cay Resort

10/10 Excellent

"Room was very clean and refreshed every day. The whole resort was clean and well maintained. Everything you need for a relaxing vacation was right there on the resort "

[](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg)

### Cheeca Lodge & Spa

10/10 Excellent

"It was over the top amazing"

[](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg)

### Waterside Suites & Marina

10/10 Excellent

"Great view from the balcony. Quiet, spacious "

[](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Hadley Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg)

### Hadley Resort and Marina

10/10 Excellent

"Patio nice , pool area good , good walk to things to do ,dive museum , brewery, shopping. "

[](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information)

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg)

### La Siesta Resort & Villas

10/10 Excellent

"Great accommodations, very peaceful setting "

[](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information)

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"Outstanding staff!"

[](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

![Breezy Palms Resort](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg)

### Breezy Palms Resort

10/10 Excellent

"Clean room and huge "

[](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information)

![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)

![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8_y.jpg)

### Lime Tree Bay Resort

10/10 Excellent

"This place is the best kept secret "

[](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

## Find out more about Upper Matecumbe Key

## Upper Matecumbe Key Condo Resorts information

| Number of reviews | 12,019          |
| ----------------- | --------------- |
| Accommodation     | 1 Condo Resorts |
| Lowest Price      | CA $231         |
| Highest Price     | CA $3,290       |

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