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Search results; Over 1,000 homes in Islamorada

Guest favourite
Apartment in Islamorada
Bayside Condo at FYC with Marina, Pool & Beach
3 bedrooms, 6 beds, 2 private bathrooms
1–8 Aug
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4.77 out of 5 average rating, 71 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
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds, 2 bathrooms
19–24 Sept
4.98 out of 5 average rating, 65 reviews
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
Home in Islamorada
Margaritaville
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
4.88 out of 5 average rating, 8 reviews
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
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, 214 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
22–29 Aug
New place to stay
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
6–13 Jul
New place to stay
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
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
28 Nov – 5 Dec
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
5.0 out of 5 average rating, 84 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
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
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
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
Summer-Fall Super Discounts- Check Availability!
4 bedrooms, 5 beds, 4.5 bathrooms
6–13 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 37 reviews
Superhost
Home in Duck Key
Private Paradise in the Florida Keys
3 bedrooms, 4 beds, Toilet with sink
31 Aug – 5 Sept
4.2 out of 5 average rating, 5 reviews