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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
2BR Island Cottage | Pool • Grill • Near Robbie’s
2 bedrooms, 3 beds, 1 private bathroom
23–28 Nov
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4.96 out of 5 average rating, 151 reviews
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
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, 2 bathrooms
15–20 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 3 Oct
4.97 out of 5 average rating, 219 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
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, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.95 out of 5 average rating, 105 reviews
Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
17–24 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
12–18 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
20–26 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
26 Sept – 3 Oct
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 5 reviews
Home in Islamorada
Charming Beach House directly ON the beach
4 bedrooms, 6 beds, 3 bathrooms
1–8 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds, 3.5 bathrooms
24–31 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 123 reviews