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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
29 Oct – 3 Nov
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4.98 out of 5 average rating, 62 reviews
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds
19–26 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds
15–20 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Islamorada
The HMH House
1 bedroom, 2 beds
13–18 Sept
4.97 out of 5 average rating, 58 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
20–26 Sept
4.97 out of 5 average rating, 35 reviews
Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 3 queen beds
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds
14–21 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Key Largo
Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
5 bedrooms, 9 beds
13–18 Sept
4.99 out of 5 average rating, 159 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
13–18 Sept
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds
13–19 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 king bed
27 Jun – 2 Jul
4.97 out of 5 average rating, 71 reviews
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds
24–31 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
2 bedrooms, 2 beds
18–23 Oct
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Home in Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
3 bedrooms, 4 beds
28 Nov – 3 Dec
4.91 out of 5 average rating, 54 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds
26 Sept – 3 Oct
4.91 out of 5 average rating, 23 reviews