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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
9–14 Jul
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4.93 out of 5 average rating, 385 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
24–29 Jul
New place to stay
Home in Islamorada
Margaritaville
3 bedrooms, 3 beds
5–10 Aug
4.88 out of 5 average rating, 8 reviews
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
2 bedrooms, 2 beds
9–14 Aug
4.86 out of 5 average rating, 35 reviews
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
4 bedrooms, 5 beds
7–14 Jul
5.0 out of 5 average rating, 7 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
13–18 Jul
4.8 out of 5 average rating, 50 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds
22–29 Aug
New place to stay
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds
19–24 Sept
5.0 out of 5 average rating, 110 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
4–11 Sept
5.0 out of 5 average rating, 52 reviews
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
4 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Islamorada
Island Paradise in Anglers Reef!
2 bedrooms, 3 beds
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
12–17 Jul
4.91 out of 5 average rating, 34 reviews
Home in Marathon
Special-New Oceanfront Home-5Ksf under $1K a nite!
5 bedrooms, 5 beds
12–19 Jul
New place to stay
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
25 Jul – 1 Aug
4.97 out of 5 average rating, 214 reviews
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms
7–14 Jul
Featured hotel
Hotel in Islamorada
Matacumbe courtyard view room two queens Lanai
1 bedroom, 2 queen beds
19–24 Jul
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds
28 Nov – 5 Dec
4.97 out of 5 average rating, 145 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
Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds
18–25 Jul
4.9 out of 5 average rating, 10 reviews