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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
29 Jul – 3 Aug
,
4.93 out of 5 average rating, 384 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
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.86 out of 5 average rating, 35 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
1–6 Jul
New place to stay
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
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 110 reviews
Superhost
Home in Islamorada
Brand-New 4BR Island Home in Central Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
1–8 Jul
New place to stay
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, 213 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
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
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds, 3.5 bathrooms
23–30 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Islamorada
Island Paradise in Anglers Reef!
2 bedrooms, 3 beds, 2.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
2–7 Jul
4.91 out of 5 average rating, 34 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
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
Superhost
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds, 5 bathrooms
7–12 Aug
Superhost
Home in Islamorada
Pineapple Beach
5 bedrooms, 13 beds, 4.5 bathrooms
4–11 Jul
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 78 reviews
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
2 bedrooms, 1 bed, 1 bathroom
13–18 Jul
New place to stay