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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Islamorada holiday homes

2 bedrooms, iron/ironing board, WiFi, bed sheets

1. Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (4 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is £315
includes taxes & fees
12 Sept - 13 Sept
Little Peace of Haven
Smart TV

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (40 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is £299
includes taxes & fees
31 Aug - 1 Sept
Charming Home in Key Largo
Beach nearby, sun-loungers, beach towels

3. 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 £373
includes taxes & fees
25 Sept - 26 Sept
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Outdoor dining

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

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
10.0 out of 10, Exceptional, (3 reviews)
The price is £645
includes taxes & fees
8 Sept - 9 Sept
Waterfront / Ocean Access Canal / Kamp Key / Homes
Interior

5. 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
9.0 out of 10, Wonderful, (22 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is £370
includes taxes & fees
9 Sept - 10 Sept
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Beach nearby

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

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (149 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 £416
includes taxes & fees
31 Aug - 1 Sept
Key Largo Villa, Kawama P6, 3/3
Beach

7. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (230 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 £409
includes taxes & fees
31 Aug - 1 Sept
Key Largo Kawama Villa L1, 3/3
Dining

8. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is £618
includes taxes & fees
15 Sept - 16 Sept
Sunrise Escape - Ocean Front Villa - Sleeps 10
Property grounds

9. 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)
"Especially enjoyed the private lagoon."
United States
Tom W.
The price is £452
includes taxes & fees
31 Aug - 1 Sept
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Beach nearby

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

Key Largo Villa, Kawama K5, 3/3
Key Largo
10.0 out of 10, Exceptional, (67 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is £444
includes taxes & fees
31 Aug - 1 Sept
Key Largo Villa, Kawama K5, 3/3
Outdoor dining

11. Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (184 reviews)
"Excellent property and the property manager was great to work with. Excellent communication"
United States
Anonymous traveller
The price is £459
includes taxes & fees
31 Aug - 1 Sept
Oceanside Kawama Villa R5
Microwave, oven, stovetop, dishwasher

12. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is £543
includes taxes & fees
9 Sept - 10 Sept
Oceanside Retreat w/Rooftop, Pool & Kayaks
A heated pool

13. 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, (17 reviews)
"Place was perfect in many ways!!!!"
United States
Brandon M.
The price is £705
includes taxes & fees
9 Sept - 10 Sept
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Dining

14. Waterfront Cottage - Beach and Dockage! Open Water Views!

Waterfront Cottage - Beach and Dockage! Open Water Views!
Key Largo
9.4 out of 10, Exceptional, (46 reviews)
"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
Shane F.
The price is £431
includes taxes & fees
16 Sept - 17 Sept
Waterfront Cottage - Beach and Dockage! Open Water Views!
TV, video games

15. Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo
9.6 out of 10, Exceptional, (5 reviews)
"Loved the location and views, house is amazing"
United States
Dan L.
Key Largo Oasis Oceanfront with Pool & Hot Tub
Interior

16. El Encanto

El Encanto
Key Largo
The price is £483
includes taxes & fees
31 Aug - 1 Sept
El Encanto
Outdoor pool, a heated pool

17. 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, (40 reviews)
"Great stay"
United States
Kathleen H.
The price is £638
includes taxes & fees
23 Sept - 24 Sept
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Outdoor dining

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, (3 reviews)
"This property and the entire community was amazing. This was a fantastic vacation. One of the best we have had in years!"
United States
Gmac W.
The price is £1,358
includes taxes & fees
28 Sept - 29 Sept
Private Beach / Private overwater dock / Heated Pool / Mahi Key
Beach nearby

19. Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
9.4 out of 10, Exceptional, (135 reviews)
"Great villa!"
United States
Georgi T.
The price is £464
includes taxes & fees
31 Aug - 1 Sept
Key largo Kawama Villa N2
Beach

20. Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina
Key Largo
9.6 out of 10, Exceptional, (151 reviews)
"Everything was great!"
United States
Kim W.
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Everything was fabulous. We stayed in a newer building on the beach. The room, service, and staff were all 10/10. Shout out to Dee at the atlantics edge restaurant for her great dinner service. Our room was clean and replenished daily. The pool and poolside service also excellent. The only downside of our stay was the seaweed. The smell was bad at times. We would've liked to spend more time on the beach and look forward to coming back for that."
Bethanne 4-night trip
Posted 4 hours ago
Cheeca Lodge & Spa

Find out more about Islamorada

Islamorada Holiday Homes information

Number of reviews
989
Accommodation
571 Holiday Homes
Lowest Price
£299
Highest Price
£1,358

Explore a world of travel with Expedia