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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
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
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
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
25 Jul – 1 Aug
4.97 out of 5 average rating, 212 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Retreat: Ocean & Pool Views, Gym, PB Court
3 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
4.89 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Tavernier
Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft
2 bedrooms, 3 beds, 2 bathrooms
4–9 Jul
4.99 out of 5 average rating, 95 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
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
5–12 Aug
5.0 out of 5 average rating, 14 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
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
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
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
1–7 Aug
4.97 out of 5 average rating, 30 reviews
Superhost
Flat in Islamorada
Isla Santorini | Islamorada Waterfront Condo, Pool
2 bedrooms, 3 beds, 2.5 bathrooms
29 Jul – 5 Aug
New place to stay
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
4–11 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Apartment in Tavernier
Key Largo 1BR Condo w/ Ocean View & Balcony
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.83 out of 5 average rating, 6 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