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

Search Vacation Homes in Islamorada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Islamorada vacation homes

Interior

1. Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥24,003
￥63,636 total
includes taxes & fees
Sep 22 - Sep 23
Little Peace of Haven
Smart TV

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 ￥22,591
￥64,556 total
includes taxes & fees
Oct 1 - Oct 2
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 ￥22,355
￥77,745 total
includes taxes & fees
Sep 25 - Sep 26
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Terrace/patio

4. 2. Waterfront Key Largo Studio | Fish & Relax

2. Waterfront Key Largo Studio | Fish & Relax
Key Largo
10.0 out of 10, Exceptional, (16 reviews)
"A very clean and accommodating place. Will stay again."
United States
James G.
2. Waterfront Key Largo Studio | Fish & Relax
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
9.2 out of 10, Wonderful, (23 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Beach

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 ￥41,181
￥86,334 total
includes taxes & fees
Sep 22 - Sep 23
Key Largo Kawama Villa L1, 3/3
Dining

7. 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 ￥36,004
￥113,886 total
includes taxes & fees
Sep 23 - Sep 24
Sunrise Escape - Ocean Front Villa - Sleeps 10
Pool

8. 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.
1. Key Largo Waterfront Studio | Canal & Ocean
Beach nearby

9. 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 ￥39,220
￥89,461 total
includes taxes & fees
Sep 22 - Sep 23
Key Largo Villa, Kawama P6, 3/3
Property grounds

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, (62 reviews)
"Especially enjoyed the private lagoon."
United States
Tom W.
The price is ￥45,181
￥96,324 total
includes taxes & fees
Sep 22 - Sep 23
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Beach nearby

11. 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.
Key Largo Villa, Kawama K5, 3/3
Outdoor dining

12. 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 ￥47,770
￥97,776 total
includes taxes & fees
Sep 22 - Sep 23
Oceanside Kawama Villa R5
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, (18 reviews)
"Place was perfect in many ways!!!!"
United States
Brandon M.
The price is ￥50,406
￥136,619 total
includes taxes & fees
Sep 22 - Sep 23
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
House | 3 bedrooms

14. 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 ￥233,340
￥396,610 total
includes taxes & fees
Oct 14 - Oct 15
Beach Residence Private Overwater Dock Heated Pool Mahi Key
Outdoor dining

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

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is ￥64,964
￥153,036 total
includes taxes & fees
Oct 12 - Oct 13
Waterfront / Ocean Access Canal / Kamp Key / Homes
Dining

16. 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 ￥47,064
￥92,031 total
includes taxes & fees
Sep 28 - Sep 29
Waterfront Cottage - Beach and Dockage! Open Water Views!
Microwave, oven, stovetop, dishwasher

17. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is ￥81,185
￥157,950 total
includes taxes & fees
Sep 22 - Sep 23
Oceanside Retreat w/Rooftop, Pool & Kayaks
TV, video games

18. 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 ￥63,572
￥136,165 total
includes taxes & fees
Oct 7 - Oct 8
Key Largo Oasis Oceanfront with Pool & Hot Tub
Interior

19. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is ￥56,477
￥119,111 total
includes taxes & fees
Sep 28 - Sep 29
El Encanto: private saltwater pool & tiki lounge
On the beach, sun loungers, beach towels

20. NEW! Casa Largo - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks

NEW! Casa Largo - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks
Key Largo
10.0 out of 10, Exceptional, (17 reviews)
"Pool was nice and kitchen had everything needed"
United States
Sam A.
NEW! Casa Largo - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks
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
"Loved the room, quiet vibe, designated parking, the water front area, and staff. Nice surrounding area. You need a car if you want to go to Key West or nearby cities. If you want activity recommend planning ahead. We were celebrating wedding anniversary and this fit the bill. Loved it and would come back. Things to be mindful of. Yes there is a resort fee and the property holds a fee per day for Incidentals. Having the ability to know it was negotiable would have been better than finding out when I checked out. Adult pool only was nice and relaxing. The other pools were nice but very lively, if you want to chill the other pools may not be your thing. We wanted to go to a night club with dancing but there were none in this area near the resort. We went to Hog heaven, live music was great but not a night club. The Cheeca Lodge and Spa was wonderful!"
Chrisandra 6-night trip
Posted 8 hours ago
Cheeca Lodge & Spa

Find out more about Islamorada

Islamorada Vacation Homes information

Number of reviews
998
Accommodation
577 Vacation Homes
Lowest Price
￥63,636
Highest Price
￥396,610