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

Islamorada Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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
10.0 out of 10, Exceptional, (5 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is CA $215
CA $594 total
includes taxes & fees
Oct 29 - Oct 30
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 $158
CA $521 total
includes taxes & fees
Oct 29 - Oct 30
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 $279
CA $545 total
includes taxes & fees
Nov 9 - Nov 10
4. Cozy Key Largo Waterfront Studio | Dive
A modern kitchen with white cabinetry, a granite countertop, and a ceiling fan.

4. 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 $743 total
includes taxes & fees
Nov 1 - Nov 2
Keys Cottage with Beach and Dockage! Bayfront Property!
Beach

5. 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 $351
CA $808 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Villa, Kawama P6, 3/3
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

6. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (231 reviews)
"Love the place , only problem with out a gulf car the beach and fishing area is too far away"
United States
Dayanis
The price is CA $369
CA $806 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Kawama Villa L1, 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 $525
CA $1,173 total
includes taxes & fees
Oct 29 - Oct 30
Oceanside Retreat w/Rooftop, Pool & Kayaks
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

8. New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great "
United States
Ravone L.
The price is CA $697
CA $1,396 total
includes taxes & fees
Nov 1 - Nov 2
New Oceanside Paradise with Pool and Waterfront Views!
A modern indoor space with a pool, white wicker furniture, and a white crib.

9. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is CA $506
CA $1,046 total
includes taxes & fees
Oct 29 - Oct 30
El Encanto: private saltwater pool & tiki lounge
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

10. 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 $351
CA $808 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Villa, Kawama K5, 3/3
Beach

11. Kawama G12 Upscale OceansideVilla with Marina 2/2

Kawama G12 Upscale OceansideVilla with Marina 2/2
Key Largo
10.0 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, well stocked! Our host was not easy to get a hold of, but we would definitely stay again! "
United States
Brooke B.
Kawama G12 Upscale OceansideVilla with Marina 2/2
BBQ charcoal grills and tikies by the ocean

12. 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 $428
CA $883 total
includes taxes & fees
Oct 31 - Nov 1
Oceanside Kawama Villa R5
An aerial view of a resort with multiple buildings, a central pool area, and a beach.

13. 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 $386
CA $862 total
includes taxes & fees
Nov 1 - Nov 2
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A natural rock formation with a water feature, including a waterfall and a viewing platform.

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 $488
CA $1,320 total
includes taxes & fees
Oct 29 - Oct 30
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

15. 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 $349
CA $1,067 total
includes taxes & fees
Oct 29 - Oct 30
Sunrise Escape - Ocean Front Villa - Sleeps 10
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

16. 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 $356
CA $700 total
includes taxes & fees
Oct 29 - Oct 30
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A covered walkway with a brick floor, a red umbrella, a white chair, and a fountain.

17. 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 $1,405
CA $1,605 total
includes taxes & fees
Oct 29 - Oct 30
The Coral House - Bayside Retreat for 6-8 guests
A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

18. 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 $2,332
CA $4,104 total
includes taxes & fees
Nov 20 - Nov 21
Private Beach / Private overwater dock / Heated Pool / Mahi Key
A natural rock formation with a water feature.

19. NEW! 4-Story Villa in Marina Resort with Private Rooftop, 2 pools and Hot tubs

NEW! 4-Story Villa in Marina Resort with Private Rooftop, 2 pools and Hot tubs
Rock Harbor
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed our stay very much. Plenty of space for the 6 of us. Beds were very comfy. Kitchen was well stocked. We really liked the variety of amenities of the Mariners Club."
United States
Lisa B.
NEW! 4-Story Villa in Marina Resort with Private Rooftop, 2 pools and Hot tubs
A beach setting with a thatched umbrella, a small round table, and two chairs.

20. 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 $369
CA $806 total
includes taxes & fees
Oct 29 - Oct 30
Kawama L4 - Upscale Oceanside Villa with Marina
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 1 hour ago
Fisher Inn Resort & Marina

Find out more about Islamorada

Islamorada Vacation Homes information

Number of reviews
1,101
Accommodation
574 Vacation Homes
Lowest Price
CA $521
Highest Price
CA $4,104

Explore a world of travel with Expedia