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

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Check prices for these dates

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

Our top choices for Islamorada vacation homes

A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

1. 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 ￥16,022
￥56,570 total
includes taxes & fees
Aug 26 - Aug 27
Charming Home in Key Largo
A bedroom with a wooden bed, white bedding, two bedside tables with lamps, a ceiling fan, and a window with blinds.

2. 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 ￥24,341
￥67,236 total
includes taxes & fees
Sep 1 - Sep 2
Little Peace of Haven
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
10.0 out of 10, Exceptional, (3 reviews)
"Great VRBO we had an awesome vaction."
United States
Robert E.
The price is ￥52,182
￥139,783 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront / Ocean Access Canal / Kamp Key / Homes
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

4. 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 ￥38,878
￥119,903 total
includes taxes & fees
Sep 23 - Sep 24
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.

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 ￥33,642
￥70,828 total
includes taxes & fees
Aug 26 - Aug 27
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
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, (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 ￥41,724
￥91,129 total
includes taxes & fees
Aug 26 - Aug 27
Key Largo Kawama Villa L1, 3/3
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

7. 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 ￥45,778
￥98,390 total
includes taxes & fees
Aug 26 - Aug 27
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

8. 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 traveler
The price is ￥48,400
￥99,860 total
includes taxes & fees
Aug 26 - Aug 27
Oceanside Kawama Villa R5
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

9. 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 ￥42,318
￥94,698 total
includes taxes & fees
Sep 14 - Sep 15
Key Largo Villa, Kawama K5, 3/3
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

10. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is ￥47,923
￥118,230 total
includes taxes & fees
Sep 14 - Sep 15
Oceanside Retreat w/Rooftop, Pool & Kayaks
A natural rock formation with a water feature, including a waterfall and a viewing platform.

11. 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 ￥48,944
￥141,591 total
includes taxes & fees
Aug 26 - Aug 27
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
A swimming pool with blue lounge chairs, palm trees, and a clear blue sky.

12. Mariner's Club 606 • Clean & Reliable 4/4 • Amazing Pools & Resort Amenities

Mariner's Club 606 • Clean & Reliable 4/4 • Amazing Pools & Resort Amenities
Rock Harbor
10.0 out of 10, Exceptional, (158 reviews)
"Host was very good with providing information. Nice place stay."
United States
Thomas M.
The price is ￥52,851
￥160,729 total
includes taxes & fees
Sep 1 - Sep 2
Mariner's Club 606 • Clean & Reliable 4/4 • Amazing Pools & Resort Amenities
A beach setting with a thatched umbrella, a small round table, and two chairs.

13. 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 ￥49,235
￥100,992 total
includes taxes & fees
Aug 26 - Aug 27
Key largo Kawama Villa N2
A modern kitchen with white cabinetry, a granite countertop, and a ceiling fan.

14. 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 ￥47,685
￥94,357 total
includes taxes & fees
Aug 26 - Aug 27
Keys Cottage with Beach and Dockage! Bayfront Property!
A modern indoor space with a pool, white wicker furniture, and a white crib.

15. El Encanto

El Encanto
Key Largo
The price is ￥40,771
￥99,792 total
includes taxes & fees
Sep 2 - Sep 3
El Encanto
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

16. 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 ￥66,014
￥141,681 total
includes taxes & fees
Sep 16 - Sep 17
New Oceanside Paradise with Pool and Waterfront Views!
A resort with a large, curved swimming pool surrounded by palm trees and lounge chairs.

17. 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, (150 reviews)
"Very spacious, clean, and well located accommodation, communicative host, nicely decorated!"
United States
Henah P.
The price is ￥79,346
￥144,621 total
includes taxes & fees
Aug 26 - Aug 27
Marina Villa 212 3/3 Pools, Marina and Ocean views
A beach setting with a thatched umbrella, a small round table, and two chairs.

18. Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina
Key Largo
9.6 out of 10, Exceptional, (151 reviews)
"This place had everything we needed! We had a wonderful stay and would love to return. "
United States
Amanda M.
The price is ￥48,400
￥99,860 total
includes taxes & fees
Aug 27 - Aug 28
Kawama L4 - Upscale Oceanside Villa with Marina
A dining area with a wooden table and white chairs, a ceiling fan, and a kitchen with white cabinets and a marble backsplash.

19. 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 ￥47,685
￥94,357 total
includes taxes & fees
Aug 31 - Sep 1
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.

20. 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.
The price is ￥66,548
￥142,284 total
includes taxes & fees
Sep 9 - Sep 10
Key Largo Oasis Oceanfront with Pool & Hot Tub
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

The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Excellent place to stay!"
Jose 3-night trip
Posted 3 hours ago
The Caribbean Resort

Find out more about Islamorada

Islamorada Vacation Homes information

Number of reviews
1,076
Accommodation
577 Vacation Homes
Lowest Price
￥56,570
Highest Price
￥160,729