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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
21–26 Sept
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4.93 out of 5 average rating, 394 reviews
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Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
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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, 220 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
20–27 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds, 4 bathrooms
30 Oct – 4 Nov
4.88 out of 5 average rating, 48 reviews
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Guest favourite
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 79 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
3–10 Oct
New place to stay
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Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 69 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
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Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
22–27 Sept
4.99 out of 5 average rating, 113 reviews
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
20–27 Sept
5.0 out of 5 average rating, 81 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
20–26 Sept
5.0 out of 5 average rating, 17 reviews
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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
7–12 Nov
4.86 out of 5 average rating, 7 reviews
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Superhost
Townhouse in Marathon
Florida Keys Group Getaway at Salt Kissed
7 bedrooms, 9 beds, 6 bathrooms
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Tavernier
Atlantic Serenity 2407 Ocean Pointe 2 BA 2 BR
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 11 reviews