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

Islamorada Vacation Rentals

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Our top choices for Islamorada vacation homes

1. Little Peace of Haven

Little Peace of Haven
Key Largo
9.0 out of 10, Wonderful, (6 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is CA $197
CA $550 total
includes taxes & fees
Nov 29 - Nov 30
Little Peace of Haven

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is CA $161
CA $505 total
includes taxes & fees
Nov 16 - Nov 17
Charming Home in Key Largo

3. Key Lime Cottage in Islamorada

Key Lime Cottage in Islamorada
Matecumbe
10.0 out of 10, Exceptional, (49 reviews)
"Cute little cottage perfect for a weekend getaway. Enjoyed pool area, convenient location on our road trip down the Keys!"
United States
Karen L.
The price is CA $335
CA $615 total
includes taxes & fees
Nov 16 - Nov 17
Key Lime Cottage in Islamorada

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

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
9.0 out of 10, Wonderful, (7 reviews)
"Great VRBO we had an awesome vaction."
United States
Robert E.
The price is CA $595
CA $1,416 total
includes taxes & fees
Dec 2 - Dec 3
Waterfront / Ocean Access Canal / Kamp Key / Homes

5. 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 $561
CA $1,176 total
includes taxes & fees
Nov 17 - Nov 18
New Oceanside Paradise with Pool and Waterfront Views!

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

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (152 reviews)
"The property was very nice, we recommend it."
United States
Gaby
The price is CA $372
CA $841 total
includes taxes & fees
Nov 17 - Nov 18
Key Largo Villa, Kawama P6, 3/3

7. Waterfront 3BR Retreat: Pool, Spa & Kayaks

Waterfront 3BR Retreat: Pool, Spa & Kayaks
Key Largo
The price is CA $541
CA $1,128 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront 3BR Retreat: Pool, Spa & Kayaks

8. Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (138 reviews)
"Would definitely come back to the same place over and over again !!"
United States
madi a.
The price is CA $360
CA $764 total
includes taxes & fees
Dec 6 - Dec 7
Casa Largo

9. 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 $302
CA $607 total
includes taxes & fees
Nov 17 - Nov 18
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

10. 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, (64 reviews)
"Great house and even better location!"
United States
Sofia C.
The price is CA $385
CA $829 total
includes taxes & fees
Nov 16 - Nov 17
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

11. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (77 reviews)
"Great place!"
United States
Jessica S.
The price is CA $355
CA $1,084 total
includes taxes & fees
Nov 16 - Nov 17
Sunrise Escape - Ocean Front Villa - Sleeps 10

12. 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, (21 reviews)
"Beautiful property Great location Gorgeous pool and great facilities available Perfect stay"
United Kingdom
Jennifer
The price is CA $497
CA $1,344 total
includes taxes & fees
Nov 19 - Nov 20
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

13. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is CA $514
CA $1,053 total
includes taxes & fees
Nov 16 - Nov 17
El Encanto: private saltwater pool & tiki lounge

14. 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

15. 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)
"Nice place with beautiful pool."
United States
Steven J.
Mariner's Club 606 • Spacious 4/4 • Pools, Marina & Pickleball

16. 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 CA $499
CA $937 total
includes taxes & fees
Dec 2 - Dec 3
Keys Cottage with Beach and Dockage! Bayfront Property!

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, (152 reviews)
"Great location in Key Largo! Quiet, clean and relaxing."
United States
Julie P.
The price is CA $599
CA $1,098 total
includes taxes & fees
Nov 16 - Nov 17
Marina Villa 212 3/3 Pools, Marina and Ocean views

18. FULL TIME LIC OWNER - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!

FULL TIME LIC OWNER - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Rock Harbor
9.4 out of 10, Exceptional, (41 reviews)
"Great stay"
United States
Kathleen H.
The price is CA $678
CA $1,493 total
includes taxes & fees
Dec 6 - Dec 7
FULL TIME LIC OWNER - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!

19. 208 Mariners Club - Island Life! Tropical Comfort & Marina Views

208 Mariners Club - Island Life! Tropical Comfort & Marina Views
Rock Harbor
9.8 out of 10, Exceptional, (93 reviews)
"Great place"
United States
Patrick G.
The price is CA $2,387
CA $3,864 total
includes taxes & fees
Nov 16 - Nov 17
208 Mariners Club - Island Life! Tropical Comfort & Marina Views

20. 207 Mariners Club - Marina Views, Island Breezes & Room to Unwind!

207 Mariners Club - Marina Views, Island Breezes & Room to Unwind!
Rock Harbor
9.4 out of 10, Exceptional, (49 reviews)
"Amazing property, great location. Would definitely stay there again! "
United States
Jamie G.
The price is CA $2,122
CA $3,528 total
includes taxes & fees
Nov 16 - Nov 17
207 Mariners Club - Marina Views, Island Breezes & Room to Unwind!
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

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Islamorada Vacation Homes information

Number of reviews
925
Accommodation
574 Vacation Homes
Lowest Price
CA $505
Highest Price
CA $3,864

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