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

Search Holiday Homes in Islamorada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Islamorada holiday 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 £321
includes taxes & fees
15 Oct - 16 Oct
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 £276
includes taxes & fees
15 Oct - 16 Oct
Charming Home in Key Largo
A two-story building with a pool, a boat dock, and a table set for dining.

3. Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is £710
includes taxes & fees
26 Oct - 27 Oct
Waterfront / Ocean Access Canal / Kamp Key / Homes
A waterfront patio with a view of the sunset, a pool, and lounge chairs.

4. 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 £297
includes taxes & fees
9 Nov - 10 Nov
4. Cozy Key Largo Waterfront Studio | Dive
A beach with a wooden structure and a signpost indicating directions to various locations.

5. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (67 reviews)
"The pool was clean and enjoying "
United States
Aaron G.
The price is £467
includes taxes & fees
19 Oct - 20 Oct
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

6. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is £609
includes taxes & fees
26 Oct - 27 Oct
Oceanside Retreat w/Rooftop, Pool & Kayaks
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

7. 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 £716
includes taxes & fees
19 Oct - 20 Oct
New Oceanside Paradise with Pool and Waterfront Views!
A beach setting with a thatched umbrella, a small round table, and two chairs.

8. Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina
Key Largo
9.6 out of 10, Exceptional, (154 reviews)
"Very well appointed!! Nicely decorated and very clean."
United States
Teresa K.
Kawama L4 - Upscale Oceanside Villa with Marina
A marina with boats docked, a long building with a sloped roof, and a clear view of the water and distant land.

9. Lagoon Views, 2 Pools & Beach in Gated Key Largo Resort Near Pennekamp

Lagoon Views, 2 Pools & Beach in Gated Key Largo Resort Near Pennekamp
Key Largo
10.0 out of 10, Exceptional, (16 reviews)
"Very clean place. Would stay again!"
United States
Carmen W.
Lagoon Views, 2 Pools & Beach in Gated Key Largo Resort Near Pennekamp
A modern indoor space with a pool, white wicker furniture, and a white crib.

10. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is £551
includes taxes & fees
18 Oct - 19 Oct
El Encanto: private saltwater pool & tiki lounge
BBQ charcoal grills and tikies by the ocean

11. 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.
Oceanside Kawama Villa R5
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

12. 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, (62 reviews)
"Great house and even better location!"
United States
Sofia C.
The price is £473
includes taxes & fees
17 Oct - 18 Oct
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.

13. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (74 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is £606
includes taxes & fees
11 Nov - 12 Nov
Sunrise Escape - Ocean Front Villa - Sleeps 10
A pool with a waterfall feature, surrounded by stone walls, with boats docked in the background.

14. FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!

FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Rock Harbor
9.4 out of 10, Exceptional, (41 reviews)
"Great stay"
United States
Kathleen H.
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
A modern kitchen with white cabinetry, a granite countertop, and a ceiling fan.

15. 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 £592
includes taxes & fees
15 Oct - 16 Oct
Keys Cottage with Beach and Dockage! Bayfront Property!
A swimming pool with blue lounge chairs, palm trees, and a clear blue sky.

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.
The price is £757
includes taxes & fees
18 Oct - 19 Oct
Mariner's Club 606 • Spacious 4/4 • Pools, Marina & Pickleball
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

17. 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.
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

18. 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.
Key Largo Villa, Kawama K5, 3/3
A covered walkway with a brick floor, a red umbrella, a white chair, and a fountain.

19. 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 £851
includes taxes & fees
15 Oct - 16 Oct
The Coral House - Bayside Retreat for 6-8 guests
A resort with a large, curved swimming pool surrounded by palm trees and lounge chairs.

20. Marina Villa 212 3/3 Pools, Marina and Ocean views

Marina Villa 212 3/3 Pools, Marina and Ocean views
Rock Harbor
9.8 out of 10, Exceptional, (151 reviews)
"Very spacious, clean, and well located accommodation, communicative host, nicely decorated!"
United States
Henah P.
The price is £673
includes taxes & fees
15 Oct - 16 Oct
Marina Villa 212 3/3 Pools, Marina and Ocean views
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Estelar propiedad muy acogedora de día y de noche."
Juan 1-night trip
Posted 3 hours ago
Chesapeake Beach Resort

Find out more about Islamorada

Islamorada Holiday Homes information

Number of reviews
1,095
Accommodation
571 Holiday Homes
Lowest Price
£276
Highest Price
£851

Explore a world of travel with Expedia