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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Jul
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4.97 out of 5 average rating, 93 reviews
Superhost
Cottage in Islamorada Tavernier
Luxury Floating Cottage • Marina, dining & fun!
3 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
New place to stay
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
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
4.96 out of 5 average rating, 136 reviews
Guest favourite
Home in Key Largo
Remodeled July 2025 2/2 Townhouse
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–15 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Apartment in Tavernier
Fish at Sunrise, Cocktails at Sunset!
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.87 out of 5 average rating, 62 reviews
Guest favourite
Home in Tavernier
Luxury Treehouse | Spacious Parking |
4 bedrooms, 4 beds, 2 bathrooms
4–9 Apr
4.93 out of 5 average rating, 30 reviews
Home in Key Largo
Home in the keys with pool/boat dock/water view!
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
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
Flat in Tavernier
Condo with Pool and Beach Access
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
4.95 out of 5 average rating, 79 reviews
Guest favourite
Flat in Tavernier
Welcome to the Pelican Lodge !
2 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.91 out of 5 average rating, 33 reviews
Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
18–25 Jul
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
8–13 Jul
4.96 out of 5 average rating, 74 reviews
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
Superhost
Home in Islamorada
Waterfront / Ocean Access Canal / Kamp Key
3 bedrooms, 3 king beds, 3 bathrooms
18–25 Jul
5.0 out of 5 average rating, 3 reviews
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed, 3 bathrooms
13–18 Jul
New place to stay