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Search results; Over 1,000 homes in Islamorada

Guest favourite
Apartment in Islamorada
Just a Few Friends - Ocean View and Bring your Boa
2 bedrooms, 2 beds, 2.5 private bathrooms
20–27 Aug
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4.94 out of 5 average rating, 32 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
9–14 Aug
4.93 out of 5 average rating, 387 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 147 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds
24–29 Aug
4.87 out of 5 average rating, 46 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
21–26 Jul
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
1–8 Aug
5.0 out of 5 average rating, 28 reviews
Featured hotel
Room in Tavernier
Standard one bedroom ocean view suite
8–13 Aug
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 king bed
30 May – 4 Jun
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
9–15 Aug
4.97 out of 5 average rating, 33 reviews
Apartment in Tavernier
Friends' Getaway 1BR w/ Ocean View, Pool & Beach
1 bedroom, 2 beds
8–13 Aug
Top guest favourite
Home in Key Largo
The charm
3 bedrooms, 4 beds
19–24 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Tavernier
Key Largo Baha Penthouse Ocean Pointe 1416
2 bedrooms, 3 beds
2–7 Aug
4.97 out of 5 average rating, 37 reviews
Featured hotel
Room in Islamorada
Matacumbe courtyard view king accessible Lanai
1 king bed
8–13 Aug
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 215 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds
24–29 Aug
4.98 out of 5 average rating, 60 reviews
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds
7–12 Sept
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
9–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Apartment in Tavernier
Relax by Keys Waters Ocean Pointe Suites 2209
2 bedrooms, 4 beds
16–21 Aug
4.89 out of 5 average rating, 83 reviews