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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
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4.93 out of 5 average rating, 384 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
6–13 Jul
5.0 out of 5 average rating, 7 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds
11–18 Aug
New place to stay
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
5–10 Jul
4.8 out of 5 average rating, 50 reviews
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
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
Home in Islamorada
Brand-New 4BR Island Home in Central Islamorada
4 bedrooms, 5 beds
2–9 Jul
New place to stay
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds
10–17 Jul
5.0 out of 5 average rating, 11 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
13–18 Jul
New place to stay
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds
23–30 Aug
5.0 out of 5 average rating, 11 reviews
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
2 bedrooms, 1 bed
13–18 Jul
New place to stay
Superhost
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed
3–8 Jul
4.91 out of 5 average rating, 34 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds
2–7 Jul
New place to stay
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds
11–18 Jul
5.0 out of 5 average rating, 76 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
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
25 Jul – 1 Aug
4.97 out of 5 average rating, 213 reviews
Superhost
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds
7–12 Aug
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