Title: Upper Matecumbe Key Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca

 

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![Islamorada which includes a beach bar](https://images.trvl-media.com/place/10768/7565a3e5-4ed9-45b3-95fd-e4d0fa8cdc20.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Upper Matecumbe Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Upper Matecumbe Key Vacation Homes

![Marina](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/88377e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/a381fdfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/f0dca02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/9f308d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.6/10

Exceptional

(62)

"Great little place with awesome outdoor area. "

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

James D.

CA $177

CA $529 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Key-Largo-Hotels-Tiny-House-On-The-Water-Pool.h55185936.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/94241dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/078f0b06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/b3fdbd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/95c54ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.8/10

Exceptional

(26)

"It was clean and a very nice place to stay. Plenty of room and awesome amenities."

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

Eric M.

CA $154

CA $551 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Key-Largo-Hotels-Charming-Home-In-Key-Largo.h99961430.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/2e6dec1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/46854630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/w1536h1023x0y1-0e4e0b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/91000000/90180000/90174100/90174063/w1535h1024x1y1-14607650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.6/10

Exceptional

(81)

"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"

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

Brad W.

CA $177

CA $531 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Key-Largo-Hotels-New-Tiny-Home-Paddle-Boards.h90174063.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/33d50685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/8493fcb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/3bdab314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/af4843d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

10/10

Exceptional

(43)

"Good location. Lagoon and pool right outside door. "

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

Debra C.

CA $189

CA $594 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Key-Largo-Hotels-Marvelous-2-Bedroom-House-With-AC-In-Key-Largo.h120624610.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/25000000/24210000/24204500/24204423/32bcd8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/25000000/24210000/24204500/24204423/92474552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/25000000/24210000/24204500/24204423/49f2540a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24210000/24204500/24204423/530b0205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.0/10

Wonderful

(129)

"Very attentive, Very clean and comfortable. Great location. I loved the little lagoon in the subdivision."

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

Tracy I.

[](https://www.expedia.ca/Key-Largo-Hotels-Relax-And-Enjoy-Beautiful-Key-Largo-Townhome.h24204423.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/89000000/88940000/88936600/88936517/2ed18387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88940000/88936600/88936517/6052198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/89000000/88940000/88936600/88936517/a2c38a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/89000000/88940000/88936600/88936517/bdaf909e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

10/10

Exceptional

(14)

"My second time staying there and I will stay there in the near future! Love this place!"

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

Alejandra S.

[](https://www.expedia.ca/Key-Largo-Hotels-2-Waterfront-Retreat-W-Ocean-Access.h88936517.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/34000000/33400000/33394100/33394058/fae92d43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sport court](https://images.trvl-media.com/lodging/34000000/33400000/33394100/33394058/b787b91e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/34000000/33400000/33394100/33394058/bbaa023e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33400000/33394100/33394058/191fad2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.6/10

Exceptional

(141)

"Loved the unit and the whole property. Loved up to the hype!"

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

Bob L.

CA $437

CA $883 total

includes taxes & fees

Nov 21 - Nov 22

[](https://www.expedia.ca/Key-Largo-Hotels-Kawama-L4-Upscale-Oceanside-Villa-With-Marina.h33394058.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101390000/101384800/101384797/46d848f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/102000000/101390000/101384800/101384797/73c3cc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/102000000/101390000/101384800/101384797/60e64b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101390000/101384800/101384797/a862a694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

10/10

Exceptional

(8)

"Awesome place. Very well kept. Definitely coming back!!"

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

ERIKA R.

CA $396

CA $796 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Key-Largo-Hotels-Kawama-G12-Upscale-OceansideVilla-With-Marina-22.h101384797.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131100/72131034/4dd5b5aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/73000000/72140000/72131100/72131034/d852afe2_edited_a94e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131100/72131034/f2f66341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/73000000/72140000/72131100/72131034/1d27e2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

10/10

Exceptional

(57)

"All new and very clean. Great place to stay."

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

M D.

[](https://www.expedia.ca/Key-Largo-Hotels-Fully-Renovated-Nov-2021Waterfront-Modern-Luxury.h72131034.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/35000000/34420000/34412600/34412502/9e094b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/35000000/34420000/34412600/34412502/0eff2ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/35000000/34420000/34412600/34412502/8cbe82f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34420000/34412600/34412502/162f943b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.8/10

Exceptional

(66)

"This place was perfect for 9 people. Both the condo and the area had plenty to do "

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

Ethan

CA $360

CA $1,057 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-Largo-Hotels-Sunrise-Escape-Ocean-Front-Villa-Sleeps-10.h34412502.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27140000/27131200/27131178/62418801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27131200/27131178/4a1dc468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/28000000/27140000/27131200/27131178/a0f1cacc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27140000/27131200/27131178/w1337h900x13y0-6639d081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.4/10

Exceptional

(221)

"Great location. Nice layout. "

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

Warren M.

CA $456

CA $907 total

includes taxes & fees

Nov 21 - Nov 22

[](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Kawama-Villa-L1.h27131178.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/34000000/33940000/33939100/33939052/6aaab228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33940000/33939100/33939052/69d6dfcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33939100/33939052/c840eecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/34000000/33940000/33939100/33939052/d5c60edf_edited_19d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.8/10

Exceptional

(138)

"The property is absolutely stunning, not a detail un touched !! The property owner was very kind and accommodating, very knowledgeable and helpful with suggestions. My girls trip turned out perfectly! So thankful… I highly recommend.."

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

Shane D.

[](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Town-Home-On-A-Lagoon.h33939052.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/54000000/53710000/53703000/53703000/7c7df51a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53710000/53703000/53703000/010f7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/54000000/53710000/53703000/53703000/0163e6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/54000000/53710000/53703000/53703000/65bffc0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.6/10

Exceptional

(135)

"We live our stay, everything was super clean and house is amazing, everything was so close."

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

Ana L.

[](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Villa.h53703000.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/89000000/88880000/88870300/88870290/079bd935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/89000000/88880000/88870300/88870290/47d4df2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88880000/88870300/88870290/df75798a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/89000000/88880000/88870300/88870290/b1a8683d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.2/10

Wonderful

(11)

"Nice location. Enjoyed our stay. "

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

David C.

[](https://www.expedia.ca/Key-Largo-Hotels-1-Oceanside-Escape-With-Canal-Views-In-Key-Largo.h88870290.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/39000000/38530000/38528300/38528245/b4775a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38530000/38528300/38528245/950b499b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/39000000/38530000/38528300/38528245/db52e708.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/39000000/38530000/38528300/38528245/c86d6004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rock Harbor

10/10

Exceptional

(129)

"Great location, very clean, pool is fantastic, spacious, and modern. "

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

Joseph A.

CA $393

CA $863 total

includes taxes & fees

Nov 21 - Nov 22

[](https://www.expedia.ca/Key-Largo-Hotels-Marina-Villa-212-33-Pools.h38528245.Hotel-Information)

![Fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/34000000/33570000/33564300/33564261/ab304c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet](https://images.trvl-media.com/lodging/34000000/33570000/33564300/33564261/195d0389.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/34000000/33570000/33564300/33564261/b11e12fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/34000000/33570000/33564300/33564261/2b8abe42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.4/10

Exceptional

(46)

"This was a very cute resort, with perfect views! We were able to stay with our family and even bring our puppies. We had an absolutely amazing time!!"

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

Shane F.

CA $385

CA $777 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Cottage-Beach-And-Dockage-Open-Water-Views.h33564261.Hotel-Information)

![Smart TV, foosball](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/7d247f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/fbf9dcf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/a7af624c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/f05b8a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rock Harbor

10/10

Exceptional

(84)

"Wonderful accommodations. I would recommend to anyone. "

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

Sarah C.

[](https://www.expedia.ca/Key-Largo-Hotels-Beautiful-Oceanside-Mariners-3-Bedroom-Townhome.h72653526.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/9d06b7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/a2de89b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/7fbea524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/0c6f892e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.6/10

Exceptional

(45)

"We had fun.we will be back next year."

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

Thomas A.

CA $123

CA $409 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Key-Largo-Hotels-Cozy-Home-Beach.h55183749.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/ef27208a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/384d0829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/c9e7193d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/24334e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

9.8/10

Exceptional

(193)

"Martha was great! Property is centrally located. Beds were comfortable. Jetty is convenient for fishing. Beware of mosquitos at dark! Would definitely do again!"

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

Michael H.

CA $620

CA $1,201 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Key-Largo-Hotels-Casa-Azul-THE-Salt-Life-Meets-Luxury-Chic-With-Beachy-Vibes-Free-Golf-Cart.h34140748.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/119000000/118720000/118714200/118714103/764c67c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/119000000/118720000/118714200/118714103/758f8811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118720000/118714200/118714103/863b099e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/119000000/118720000/118714200/118714103/f222b889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key Largo

7.0/10

Good

(2)

"Fantastic property that was even better than advertised. I would definitely stay here again."

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

John D.

CA $951

CA $1,620 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Key-Largo-Hotels-Stylish-Oceanview-Kayak-Getaway-W-Pool-Hot-Tub.h118714103.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05&regionId=553248635975749648&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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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=2026-02-18&d1=2026-02-18&endDate=2026-02-21&d2=2026-02-21&lodging=CONDO)

Villas

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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=2026-02-18&d1=2026-02-18&endDate=2026-02-21&d2=2026-02-21&lodging=VACATION_HOME)

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=2026-02-18&d1=2026-02-18&endDate=2026-02-21&d2=2026-02-21&lodging=HOUSE_BOAT)

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## Top Upper Matecumbe Key Hotel Reviews

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg)

### Amara Cay Resort

10/10 Excellent

"Rooms were clean, landscape was beautiful, staff was friendly. Access to the (2) other resorts were a plus. Would stay again."

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

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

### Breezy Palms Resort

10/10 Excellent

"Room was wonderful and the view was even better!"

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

![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg)

### Islander Resort

10/10 Excellent

"Beautiful facility and grounds, wonderful location for quiet get away. The room was very clean. We really enjoyed sitting by the pool and also lounging on our private patio. Would definitely stay here again if we were in the area. A broom on the patio would be helpful to sweep away any insects."

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

![Bayside Villas by Islander Resort](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579_y.jpg)

### Bayside Villas by Islander Resort

10/10 Excellent

"Amazing"

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

![The Caribbean Resort](https://images.trvl-media.com/lodging/6000000/5820000/5812700/5812696/f1b4fe48_y.jpg)

### The Caribbean Resort

10/10 Excellent

"Great property Highly recommend "

[](https://expedia.ca/Islamorada-Hotels-The-Caribbean-Resort.h5812696.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

"Enjoyed breakfast looking out over the water. "

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

![La Jolla Resort](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92_y.jpg)

### La Jolla Resort

10/10 Excellent

"Room was nice and clean. Beach area was beautiful to watch sunset. "

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

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

### Cheeca Lodge & Spa

10/10 Excellent

"Amazing!"

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

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"Room was clean, breakfast and staff were good "

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

## Find out more about Upper Matecumbe Key

## Upper Matecumbe Key Vacation Homes information

| Number of reviews | |
| --- | --- |
| Accommodation | Vacation Homes |
| Lowest Price | |
| Highest Price | |

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-   [Flights to Islamorada](https://www.expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)
-   [Flights from Toronto to Islamorada](https://www.expedia.ca/lp/flights/178314/10768/toronto-to-islamorada)

-   [Hurricane Monument](https://www.expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction)
-   [Islamorada Vacations](https://www.expedia.ca/Islamorada.d10768.Destination-Travel-Guides)
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-   [Things to do in Islamorada](https://www.expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)

-   [Book Vacation Homes in Upper Matecumbe Key on Expedia.com](https://www.expedia.com/Upper-Matecumbe-Key-Private-Vacation-Homes.d553248635975749648-aaPrivateVacationHomes.Travel-Guide-Accommodation)