A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Islamorada vacation homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. Little Peace of Haven

Little Peace of Haven
Key Largo
9.0 out of 10, Wonderful, (6 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is CA $210
CA $584 total
includes taxes & fees
Dec 1 - Dec 2
Little Peace of Haven
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
The price is CA $201
CA $575 total
includes taxes & fees
Nov 1 - Nov 2
Charming Home in Key Largo
A table with a glass of beverage, a mug, and a plate with food, overlooking a pool with boats and palm trees under a sunset sky.

3. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"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
Brittany M.
The price is CA $276
CA $540 total
includes taxes & fees
Nov 9 - Nov 10
4. Cozy Key Largo Waterfront Studio | Dive
A beachside wooden deck with Adirondack chairs, a thatched-roof gazebo, and a grill.

4. Key Largo Villa, Kawama P6, 3/3

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (151 reviews)
"Beautiful, clean home. Loved the property and the inlet with all the fish was amazing. Would stay again."
United States
Sandra C.
The price is CA $350
CA $804 total
includes taxes & fees
Nov 1 - Nov 2
Key Largo Villa, Kawama P6, 3/3
A modern living room with a large TV, grey sofas, a coffee table with decorative items, and a kitchen in the background.

5. Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa

Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa
Key Largo
9.4 out of 10, Exceptional, (231 reviews)
"This vila was perfect for our stay! It was centrally located, clean, well stocked kitchen."
United States
Debra J.
The price is CA $391
CA $833 total
includes taxes & fees
Nov 1 - Nov 2
Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa
A beachside wooden deck with Adirondack chairs, a thatched-roof gazebo, and a grill.

6. Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3
Key Largo
10.0 out of 10, Exceptional, (68 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is CA $482
CA $971 total
includes taxes & fees
Nov 5 - Nov 6
Key Largo Villa, Kawama K5, 3/3
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

7. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is CA $661
CA $1,342 total
includes taxes & fees
Nov 12 - Nov 13
Oceanside Retreat w/Rooftop, Pool & Kayaks
A table with a glass of beverage, a mug, and a plate with food, overlooking a pool with boats and palm trees under a sunset sky.

8. 1. Key Largo Waterfront Studio | Canal & Ocean

1. Key Largo Waterfront Studio | Canal & Ocean
Key Largo
9.4 out of 10, Exceptional, (13 reviews)
"Stayed here multiple times and will continue to stay here."
United States
Monica G.
The price is CA $327
CA $599 total
includes taxes & fees
Nov 6 - Nov 7
1. Key Largo Waterfront Studio | Canal & Ocean
A pool area with lounge chairs and a hot tub, overlooking the sea.

9. Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Key Largo
7.0 out of 10, Good, (2 reviews)
"Fantastic property that was even better than advertised. I would definitely stay here again."
United States
John D.
The price is CA $688
CA $1,267 total
includes taxes & fees
Nov 4 - Nov 5
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Open kitchen

10. Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (184 reviews)
"Great place to stay"
United States
Eric B.
The price is CA $454
CA $875 total
includes taxes & fees
Nov 2 - Nov 3
Oceanside Kawama Villa R5
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

11. NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (63 reviews)
"Great house and even better location!"
United States
Sofia C.
The price is CA $385
CA $860 total
includes taxes & fees
Nov 2 - Nov 3
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

12. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (76 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is CA $386
CA $1,109 total
includes taxes & fees
Nov 11 - Nov 12
Sunrise Escape - Ocean Front Villa - Sleeps 10
A modern indoor space with a pool, white wicker furniture, and a white crib.

13. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is CA $503
CA $1,041 total
includes taxes & fees
Nov 5 - Nov 6
El Encanto: private saltwater pool & tiki lounge
A large swimming pool surrounded by palm trees and a beach, with a building in the background.

14. Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Rock Harbor
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful property Great location Gorgeous pool and great facilities available Perfect stay"
United Kingdom
Jennifer
The price is CA $487
CA $1,317 total
includes taxes & fees
Nov 1 - Nov 2
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

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

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Key Largo
9.2 out of 10, Wonderful, (24 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is CA $355
CA $692 total
includes taxes & fees
Nov 4 - Nov 5
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A resort with a large pool, palm trees, and a view of the sea.

16. Mariner's Club 606 • Spacious 4/4 • Pools, Marina & Pickleball

Mariner's Club 606 • Spacious 4/4 • Pools, Marina & Pickleball
Rock Harbor
10.0 out of 10, Exceptional, (159 reviews)
"Host was very good with providing information. Nice place stay."
United States
Thomas M.
Mariner's Club 606 • Spacious 4/4 • Pools, Marina & Pickleball
A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

17. Private Beach / Private overwater dock / Heated Pool / Mahi Key

Private Beach / Private overwater dock / Heated Pool / Mahi Key
Matecumbe
10.0 out of 10, Exceptional, (4 reviews)
"Our stay here was very nice. Everything was clean and comfortable. The pool was enjoyable the one time we used it. Sitting on the deck gazing out to sea was exactly what I needed. Spotting a crocodile swim by was exciting!"
United States
Anonymous traveller
The price is CA $2,264
CA $4,012 total
includes taxes & fees
Nov 20 - Nov 21
Private Beach / Private overwater dock / Heated Pool / Mahi Key
A modern kitchen with white cabinetry, a granite countertop, and a ceiling fan.

18. Keys Cottage with Beach and Dockage! Bayfront Property!

Keys Cottage with Beach and Dockage! Bayfront Property!
Key Largo
9.4 out of 10, Exceptional, (36 reviews)
"We had such a wonderful time here! The house was perfect and the grounds were beautiful! We will definitely come again! "
United States
Julia W.
The price is CA $350
CA $742 total
includes taxes & fees
Nov 1 - Nov 2
Keys Cottage with Beach and Dockage! Bayfront Property!
A beach setting with white chairs, a fire pit, and a thatched-roof structure.

19. Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina
Key Largo
9.6 out of 10, Exceptional, (155 reviews)
"Very well appointed!! Nicely decorated and very clean."
United States
Teresa K.
The price is CA $391
CA $797 total
includes taxes & fees
Nov 1 - Nov 2
Kawama L4 - Upscale Oceanside Villa with Marina
A covered walkway with a brick floor, a red umbrella, a white chair, and a fountain.

20. The Coral House - Bayside Retreat for 6-8 guests

The Coral House - Bayside Retreat for 6-8 guests
Key Largo
7.0 out of 10, Good, (9 reviews)
"Great location with private beach loved it "
United States
Bobby A.
The price is CA $1,227
CA $1,332 total
includes taxes & fees
Nov 29 - Nov 30
The Coral House - Bayside Retreat for 6-8 guests
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.
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Top Islamorada Hotel Reviews

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

8/10 Good
"We were disappointed in a few things, one being the comfort- the couch in our room was so uncomfortable we couldn’t sit for long at all- it was also dirty with stains- fir the cost if the room, spending some money on a new, comfortable couch with washable cushion covers wouldn’t be too much to ask- plus the resort outdoor furniture was very uncomfortable- the pieces were nice & pretty but could definitely use cushions- we used our bed pillows for our outdoor Adirondack chairs on our balcony. The other disappointment was that there were only 3 kayaks, one was broken and only one of the other two had a back- again, wouldn’t take much to have more available. The staff was wonderful though!!!"
Kelley 4-night trip
Posted 2 days ago
Fisher Inn Resort & Marina

Find out more about Islamorada

Islamorada Vacation Homes information

Number of reviews
1,256
Accommodation
574 Vacation Homes
Lowest Price
CA $540
Highest Price
CA $4,012

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