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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
Floating 2 BD, 1 BATH Private Villa Pirates Lair
2 bedrooms, 1 bed, 1 private bathroom
13–18 Jul
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4.78 out of 5 average rating, 40 reviews
Superhost
Home in Islamorada
Brand-New 4BR Island Home in Central Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
1–8 Jul
New place to stay
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
1–8 Jul
New place to stay
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Islamorada
Island Paradise in Anglers Reef!
2 bedrooms, 3 beds, 2.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 108 reviews
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
10–17 Jul
5.0 out of 5 average rating, 11 reviews
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
4 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Islamorada
Pineapple Beach
5 bedrooms, 13 beds, 4.5 bathrooms
4–11 Jul
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
1–8 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 bathrooms
7–14 Jul
4.92 out of 5 average rating, 24 reviews
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds, 3 bathrooms
27 Jul – 3 Aug
New place to stay
Featured hotel
Hotel in Islamorada
One bedroom oceanfront suite king
1 bedroom, 1 bathroom
6–11 Jul
New place to stay
Guest favourite
Home in Key Largo
Largo Getaway: 3 King Suites + In-Law Space
3 bedrooms, 13 beds, 4.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 98 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
29 Jul – 3 Aug
4.93 out of 5 average rating, 384 reviews
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
3 bedrooms, 3 beds, 3 bathrooms
1–8 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Islamorada
FL Keys Ocean Front Escape
2 bedrooms, 2 beds, 3 bathrooms
1–8 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds, 2.5 bathrooms
6–13 Jul
4.92 out of 5 average rating, 25 reviews