Title: Islamorada Vacation Home Rentals : Search Top Private Vacation Homes for Rent | 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)

# Islamorada 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=10768&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=10768&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=10768&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=10768&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Islamorada Vacation Homes

![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)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/006a1068.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)

![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)

### Charming Home in Key Largo

Key Largo

9.8/10

Exceptional

(27)

"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 $160

CA $564 total

includes taxes & fees

Nov 24 - Nov 25

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120630000/120624700/120624610/a184e1c2.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)

### Marvelous 2-bedroom house with Marina in Key Largo.

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 $190

CA $599 total

includes taxes & fees

Nov 30 - Dec 1

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

![Interior](https://images.trvl-media.com/lodging/89000000/88950000/88950000/88949924/7207b32f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88950000/88950000/88949924/b420f068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88950000/88950000/88949924/68bf65b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/89000000/88950000/88950000/88949924/2085c0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4\. Cozy Waterfront Apartment in Key Largo!

Key Largo

9.8/10

Exceptional

(11)

"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "

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

Brittany M.

CA $327

CA $585 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Key-Largo-Hotels-4-Cozy-Waterfront-Apartment-In-Key-Largo.h88949924.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24210000/24204500/24204423/c9f94390.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)

### Casa Largo

Key Largo

9.0/10

Wonderful

(129)

"We stayed in 2 vrbo properties while in Florida. This one met and exceeded our expectations. We would stay again without hesitation."

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

Kelly M.

CA $402

CA $842 total

includes taxes & fees

Nov 24 - Nov 25

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

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

![A heated pool](https://images.trvl-media.com/lodging/35000000/34420000/34412600/34412502/56e02b4d.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)

### Sunrise Escape - Ocean Front Villa - Sleeps 10

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 $353

CA $1,048 total

includes taxes & fees

Dec 1 - Dec 2

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

![Exterior](https://images.trvl-media.com/lodging/119000000/118720000/118714200/118714103/e52259ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

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 $639

CA $1,295 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)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101390000/101384800/101384797/46d848f4.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)

![Pool](https://images.trvl-media.com/lodging/102000000/101390000/101384800/101384797/56c24aea_edited_8470.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)

### Kawama G12 Upscale OceansideVilla with Marina 2/2

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.

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

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/112000000/112000000/111991400/111991301/3ad629cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111991400/111991301/w1536h1022x0y64-bd4dd7b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111991400/111991301/w1536h1021x0y65-58153f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111991400/111991301/w1536h1021x0y64-d8eb8726.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

Key Largo

9.4/10

Exceptional

(9)

"Me my wife and 2 kids 18 & 19 had a great time. Loved the lagoon and the local places to eat and drink. "

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

Craig H.

CA $358

CA $699 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-Largo-Hotels-New-Lagoon-Front-2-BR-Townhome.h111991301.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)

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

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33394100/33394058/a603509f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kawama L4 - Upscale Oceanside Villa with Marina

Key Largo

9.6/10

Exceptional

(142)

"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 $537

CA $999 total

includes taxes & fees

Dec 19 - Dec 20

[](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/34000000/33570000/33568600/33568596/bf71cb1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/34000000/33570000/33568600/33568596/f380693a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33568600/33568596/2b103074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/34000000/33570000/33568600/33568596/58e9db0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Keys Cottage with Beach and Dockage! Bayfront Property!

Key Largo

9.4/10

Exceptional

(36)

"We had such a wonderful time here! The house was perfect and the grounds were beautiful! We will definitely come again! "

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

Julia W.

CA $388

CA $783 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Key-Largo-Hotels-Keys-Cottage-With-Beach-And-Dockage-Bayfront-Property.h33568596.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)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/aa4f4444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/2018fd5c.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)

### NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

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 $625

CA $1,211 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)

![Beach](https://images.trvl-media.com/lodging/118000000/117810000/117803800/117803749/9584daa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/118000000/117810000/117803800/117803749/102b5073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117810000/117803800/117803749/ade70f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117810000/117803800/117803749/15ba51e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2-bedroom townhome in pleasant gated community located in Key Largo

Key Largo

CA $515

CA $900 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Key-Largo-Hotels-2-Bedroom-Townhome-In-Pleasant-Gated-Community-Located-In-Key-Largo.h117803749.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)

![Smart TV](https://images.trvl-media.com/lodging/54000000/53710000/53703000/53703000/05612ca0.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)

### Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

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.

CA $503

CA $983 total

includes taxes & fees

Nov 24 - Nov 25

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

![Property grounds](https://images.trvl-media.com/lodging/115000000/114400000/114399800/114399726/eb4baf6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/115000000/114400000/114399800/114399726/ba02ce94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/115000000/114400000/114399800/114399726/72ca6ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114400000/114399800/114399726/63ca9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakefront Retreat pool jacuzzi

Buccaneer Point

CA $987

CA $1,433 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-Largo-Hotels-Lakefront-Retreat-In-Key-Largo.h114399726.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/109000000/108570000/108569900/108569865/3a58408f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108570000/108569900/108569865/a0a348cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/109000000/108570000/108569900/108569865/8622f82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/109000000/108570000/108569900/108569865/4005dbb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise Point 11- New 3 bed 3 bath Oceanfront home rooftop balcony- Pets OK

Key Largo

10/10

Exceptional

(1)

"Lovely home."

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

Mary Ann C.

CA $1,347

CA $2,426 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Key-Largo-Hotels-Paradise-Point-11-New-3-Bed-3-Bath-Oceanfront-Home-Rooftop-Balcony-Pets-OK.h108569865.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/23000000/22260000/22255900/22255819/cdd6a24b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22260000/22255900/22255819/149e8059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22260000/22255900/22255819/4c8c1487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/23000000/22260000/22255900/22255819/a9026141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanside Kawama Villa R5

Key Largo

9.2/10

Wonderful

(180)

"Very very nice villa in a superb location… Abcolutely loved the property!"

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

Ricardo G.

CA $532

CA $989 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Key-Largo-Hotels-Oceanside-Kawama-Villa-R5.h22255819.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/112000000/111540000/111531300/111531293/e5e2ca28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/112000000/111540000/111531300/111531293/9bdcc74a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/112000000/111540000/111531300/111531293/42e4cd5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/112000000/111540000/111531300/111531293/844dae16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deja Blue: Ocean & Pool Views, 2 Pools, Fitness Center, Marina and more......

Rock Harbor

9.8/10

Exceptional

(6)

"This property was just as described! Very clean, great access to the pool and a beautiful view. Beds were comfortable and kitchen had everything we needed to prepare meals. Our host was easy to communicate with and the area was very safe. "

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

Laura N.

[](https://www.expedia.ca/Key-Largo-Hotels-Deja-Blue-Ocean-Pool-Views.h111531293.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/119000000/118470000/118468400/118468332/2c728157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/119000000/118470000/118468400/118468332/56b6c86a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/119000000/118470000/118468400/118468332/2782c08e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118470000/118468400/118468332/a6bb767d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! 4-Story Villa | Private Rooftop | Pool |Marina | Resort, NEW! 4-Story Villa, Private Rooftop, P...

Rock Harbor

10/10

Exceptional

(3)

"This is one of the nicest VRBO‘s I’ve ever been in. The home is extremely clean and the owner thought of everything when stocking it , Janet the host was incredible. She was super responsive and helpful. She guided us to some excellent restaurants and took care of any concerns we had immediately. I I would recommend this property to everyone"

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

Anonymous traveller

CA $887

CA $1,593 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Key-Largo-Hotels-NEW-4-Story-Resort-Villa-Rooftop-All-Private-Suites.h118468332.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34560000/34555400/34555333/19fe9188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34560000/34555400/34555333/5332034e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34560000/34555400/34555333/799dcc04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34560000/34555400/34555333/57f41650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SPACIOUS 4/3.5 VILLA! INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!

Rock Harbor

9.6/10

Exceptional

(32)

"Great place to stay. Plenty of room for everyone. Lots to do at the resort. "

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

Tandy T.

CA $698

CA $1,382 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Key-Largo-Hotels-LICENSED-MANAGER-435-LUXURY-VILLA-MOST-UPSCALE-OCEANFRONT-RESORT-IN-KL.h34555333.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)

![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)

![Marina](https://images.trvl-media.com/lodging/89000000/88940000/88936600/88936517/w1437h957x0y3-2f8b3468.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)

### 2\. Waterfront Retreat w/ Ocean Access, Key Largo!

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.

CA $361

CA $646 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Key-Largo-Hotels-2-Waterfront-Retreat-W-Ocean-Access.h88936517.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=2025-12-07&endDate=2025-12-08&regionId=10768&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FIslamorada-Private-Vacation-Homes.d10768-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FIslamorada-Private-Vacation-Homes.d10768-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Islamorada Hotel Reviews

![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 room, stunning views "

[](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information)

![Pines & Palms Resort](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg)

### Pines & Palms Resort

10/10 Excellent

"All was great!!!"

[](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

"Quiet and relaxing. Great place"

[](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.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

"Azaya at the front desk was GREAT!! Boat launch on property free for guests. Perfect location comfy rooms! "

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

![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)

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

### Chesapeake Beach Resort

10/10 Excellent

"Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms. "

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

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

### Cheeca Lodge & Spa

10/10 Excellent

"Everything about our stay was amazing and exceeded our expectations in every way!!"

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

## Find out more about Islamorada

## Islamorada Vacation Homes information

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

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-   [Luxury Hotels in Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key-Hotels-Luxury-Hotel.0-0-d553248635975749648-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Upper Matecumbe Key Hotels](https://www.expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)
-   [Vacation Homes in Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key-Private-Vacation-Homes.d553248635975749648-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Resorts in Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key-Resort-Hotels.d553248635975749648-aaResortHotels.Travel-Guide-Accommodation)
-   [Cabin Rentals in Windley Key](https://www.expedia.ca/Windley-Key-Cabins.d553248635976197663-aaCabins.Travel-Guide-Accommodation)
-   [Hotels near Windley Key Fossil Reef Geological State Park](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Hotels.0-l6282211-0.Travel-Guide-Filter-Hotels)
-   [Windley Key Hotels](https://www.expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)
-   [Inns in Windley Key](https://www.expedia.ca/Windley-Key-Inns.d553248635976197663-aaInns.Travel-Guide-Accommodation)

-   [History of Diving Museum](https://www.expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction)
-   [Hurricane Monument](https://www.expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction)
-   [Visit Matecumbe](https://www.expedia.ca/Islamorada-Matecumbe.dx855587555438403584)
-   [Visit Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key.dx553248635975749648)
-   [Windley Key Fossil Reef Geological State Park](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

-   [Drive-A-Matic Rental Cars in Windley Key](https://www.expedia.ca/Drive-A-Matic-Car-Rentals-In-Windley-Key.d553248635976197663-c1082.Car-Rental-Guide-Suppliers)
-   [Easirent.com Rental Cars in Upper Matecumbe Key](https://www.expedia.ca/Easirentcom-Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648-c1017.Car-Rental-Guide-Suppliers)
-   [Sicily By Car Rental Cars in Windley Key](https://www.expedia.ca/Sicily-By-Car-Car-Rentals-In-Windley-Key.d553248635976197663-c1048.Car-Rental-Guide-Suppliers)

-   [Things to do in Windley Key](https://www.expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)

-   [Book Vacation Homes in Islamorada on Expedia.com](https://www.expedia.com/Islamorada-Private-Vacation-Homes.d10768-aaPrivateVacationHomes.Travel-Guide-Accommodation)