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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 private bathroom
8–15 Aug
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4.97 out of 5 average rating, 215 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 50 reviews
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 28 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, 15 reviews
Guest favourite
Home in Islamorada
Boat slip included August-November 2026!
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
4.92 out of 5 average rating, 50 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 103 reviews
Top guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
4.92 out of 5 average rating, 26 reviews
Serviced apartment in Islamorada
Suites Near Lignumvitae Key! Parking, Breakfast!
1 bedroom, 1 king bed, 1 bathroom
22–27 Aug
New place to stay
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 387 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 53 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Apartment in Key Colony Beach
Exquisite Oceanfront Paradise - Key Colony Beach
1 bed, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 221 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 60 reviews
Featured hotel
Room in Tavernier
One bedroom ocean view suite - provident signature
1 bathroom
2–7 Aug
New place to stay
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.9 out of 5 average rating, 273 reviews
Guest favourite
Apartment in Tavernier
Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool
2 bedrooms, 3 beds, 2 bathrooms
15–22 Aug
4.94 out of 5 average rating, 16 reviews
Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
4.8 out of 5 average rating, 91 reviews
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 112 reviews
Top guest favourite
Townhouse in Key Largo
Luxury 3BR/3BA Condo with Sweeping Ocean Views
3 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 27 reviews