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

Holiday Homes in Islamorada

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Islamorada holiday homes

A bedroom with a wooden bed, white bedding, two bedside tables with lamps, a ceiling fan, and a window with blinds.

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 NZ$725
includes taxes & fees
11 Sept - 12 Sept
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
9.8 out of 10, Exceptional, (40 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is NZ$609
includes taxes & fees
8 Sept - 9 Sept
Charming Home in Key Largo
A wooden pier with a thatched roof, leading to a rocky beach area with clear blue water. Directional signs indicate nearby locations.

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 NZ$825
includes taxes & fees
25 Sept - 26 Sept
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A two-story building with a pool, a boat dock, and a table set for 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)
"Great VRBO we had an awesome vaction."
United States
Robert E.
The price is NZ$1,432
includes taxes & fees
8 Sept - 9 Sept
Waterfront / Ocean Access Canal / Kamp Key / Homes
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

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 NZ$747
includes taxes & fees
1 Sept - 2 Sept
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

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 NZ$970
includes taxes & fees
1 Sept - 2 Sept
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.

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 NZ$959
includes taxes & fees
1 Sept - 2 Sept
Key Largo Kawama Villa L1, 3/3
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

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 NZ$1,234
includes taxes & fees
1 Sept - 2 Sept
Sunrise Escape - Ocean Front Villa - Sleeps 10
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

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 NZ$1,035
includes taxes & fees
1 Sept - 2 Sept
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
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, (67 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is NZ$1,015
includes taxes & fees
1 Sept - 2 Sept
Key Largo Villa, Kawama K5, 3/3

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 NZ$1,050
includes taxes & fees
1 Sept - 2 Sept
Oceanside Kawama Villa R5
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

12. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is NZ$1,242
includes taxes & fees
9 Sept - 10 Sept
Oceanside Retreat w/Rooftop, Pool & Kayaks
A natural rock formation with a water feature, including a waterfall and a viewing platform.

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 NZ$1,550
includes taxes & fees
21 Sept - 22 Sept
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
A dining area with a wooden table and white chairs, a ceiling fan, and a kitchen with white cabinets and a marble backsplash.

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 NZ$963
includes taxes & fees
16 Sept - 17 Sept
Waterfront Cottage - Beach and Dockage! Open Water Views!
A modern living room with a grey sofa, a patterned armchair, and a coffee table. Large windows offer a view of the sea and buildings.

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
A modern indoor space with a pool, white wicker furniture, and a white crib.

16. El Encanto

El Encanto
Key Largo
The price is NZ$1,065
includes taxes & fees
2 Sept - 3 Sept
El Encanto
A pool with a waterfall feature, surrounded by stone walls, with boats docked in the background.

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 NZ$1,444
includes taxes & fees
23 Sept - 24 Sept
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
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, (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 NZ$3,039
includes taxes & fees
28 Sept - 29 Sept
Private Beach / Private overwater dock / Heated Pool / Mahi Key
A beach setting with a thatched umbrella, a small round table, and two chairs.

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.
Key largo Kawama Villa N2
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, (151 reviews)
"Everything was great!"
United States
Kim W.
The price is NZ$963
includes taxes & fees
1 Sept - 2 Sept
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.
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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

8/10 Good
"Great property with an amazing concept, especially in an area where there aren’t many high-end properties offering this style and experience. The facilities are excellent, and overall we really enjoyed our stay. My only negative feedback is that a few members of staff were constantly on their phones watching clips and videos, often with the volume turned up. We found this quite annoying, particularly when trying to relax quietly by the pool. It would be great if staff could be reminded to use headphones or keep phone use to a minimum in guest relaxation areas. Room maintaince could also be better."
Asoka 2-night trip
Posted 2 hours ago
Islander Resort

Find out more about Islamorada

Islamorada Holiday Homes information

Number of reviews
12,749
Accommodation
572 Holiday Homes
Lowest Price
NZ$184
Highest Price
NZ$790