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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 private bathroom
26–31 Jul
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4.8 out of 5 average rating, 90 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
13–18 Jul
New place to stay
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed, 3 bathrooms
13–18 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
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
Islamorada Bungalow # 5
2 bedrooms, 2 beds, 1 bathroom
6–11 Aug
4.85 out of 5 average rating, 34 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
17–24 Jul
4.96 out of 5 average rating, 25 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
11–18 Aug
New place to stay
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds, 3 bathrooms
8–15 Aug
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, 25 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
4.8 out of 5 average rating, 50 reviews
Featured hotel
Hotel in Islamorada
Matacumbe courtyard view king accessible Lanai
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
New place to stay
Superhost
Home in Islamorada
Pineapple Beach
5 bedrooms, 13 beds, 4.5 bathrooms
4–11 Jul
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
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
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
4.97 out of 5 average rating, 144 reviews
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
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
Featured hotel
Hotel in Islamorada
Studio suite garden view two queen accessible
1 bedroom, 2 queen beds, 1 bathroom
7–12 Aug