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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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)
The price is CA $217
CA $596 total
includes taxes & fees
Sep 30 - Oct 1
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 $204
CA $581 total
includes taxes & fees
Oct 1 - Oct 2
Charming Home in Key Largo
A modern kitchen with a built-in microwave, stove, and dishwasher.

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 $264
CA $531 total
includes taxes & fees
Sep 30 - Oct 1
4. Cozy Key Largo Waterfront Studio | Dive
A small, single-story building with a yellow door, two windows with shutters, and a blue chair outside.

4. Cozy 1-bedroom bungalow in gorgeous Key Largo with AC

Cozy 1-bedroom bungalow in gorgeous Key Largo with AC
Rock Harbor
The price is CA $228
CA $321 total
includes taxes & fees
Oct 17 - Oct 18
Cozy 1-bedroom bungalow in gorgeous Key Largo with AC
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
9.2 out of 10, Wonderful, (24 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is CA $264
CA $584 total
includes taxes & fees
Sep 30 - Oct 1
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
An aerial view of a waterfront property with a long building, a parking area, and a beach.

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

1. Key Largo Waterfront Studio | Canal & Ocean
Key Largo
9.4 out of 10, Exceptional, (13 reviews)
"Nice location. Enjoyed our stay. "
United States
David C.
The price is CA $263
CA $547 total
includes taxes & fees
Oct 4 - Oct 5
1. Key Largo Waterfront Studio | Canal & Ocean
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

7. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (73 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is CA $352
CA $1,075 total
includes taxes & fees
Sep 30 - Oct 1
Sunrise Escape - Ocean Front Villa - Sleeps 10
A modern indoor space with a pool, white wicker furniture, and a white crib.

8. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is CA $287
CA $776 total
includes taxes & fees
Sep 30 - Oct 1
El Encanto: private saltwater pool & tiki lounge
Beach

9. 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.
The price is CA $335
CA $725 total
includes taxes & fees
Sep 30 - Oct 1
Kawama G12 Upscale OceansideVilla with Marina 2/2
Beach

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

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (150 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 $376
CA $839 total
includes taxes & fees
Sep 30 - Oct 1
Key Largo Villa, Kawama P6, 3/3
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.
The price is CA $432
CA $888 total
includes taxes & fees
Sep 30 - Oct 1
Oceanside Kawama Villa R5
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

12. 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 CA $374
CA $814 total
includes taxes & fees
Oct 5 - Oct 6
Key Largo Kawama Villa L1, 3/3
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

13. 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 $364
CA $828 total
includes taxes & fees
Oct 7 - Oct 8
Key Largo Villa, Kawama K5, 3/3
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

14. 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 CA $408
CA $873 total
includes taxes & fees
Oct 2 - Oct 3
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A beach with a wooden structure and a signpost indicating directions to various locations.

15. 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 CA $354
CA $895 total
includes taxes & fees
Oct 14 - Oct 15
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A natural rock formation with a water feature, including a waterfall and a viewing platform.

16. 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, (18 reviews)
"Place was perfect in many ways!!!!"
United States
Brandon M.
The price is CA $493
CA $1,335 total
includes taxes & fees
Sep 30 - Oct 1
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

17. 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 $560
CA $1,226 total
includes taxes & fees
Sep 30 - Oct 1
New Oceanside Paradise with Pool and Waterfront Views!
A dining area with a wooden table and white chairs, a ceiling fan, and a kitchen with white cabinets and a marble backsplash.

18. 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 CA $425
CA $839 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Cottage - Beach and Dockage! Open Water Views!
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

19. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is CA $440
CA $1,070 total
includes taxes & fees
Oct 7 - Oct 8
Oceanside Retreat w/Rooftop, Pool & Kayaks
A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

20. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Beach Residence Private Overwater Dock Heated Pool Mahi Key
2.0 star property
Matecumbe
The price is CA $2,014
CA $3,462 total
includes taxes & fees
Oct 14 - Oct 15
Beach Residence Private Overwater Dock Heated Pool Mahi Key
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

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 20 hours ago
Islander Resort

Find out more about Islamorada

Islamorada Vacation Homes information

Number of reviews
933
Accommodation
574 Vacation Homes
Lowest Price
CA $531
Highest Price
CA $3,462

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