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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
1–6 Aug
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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, 4 bathrooms
24–29 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, 214 reviews
Home in Marathon
Special-New Oceanfront Home-5Ksf under $1K a nite!
5 bedrooms, 5 beds, 4.5 bathrooms
12–19 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, 36 reviews
Superhost
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 34 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, 111 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
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
4.8 out of 5 average rating, 50 reviews
Luxe
Villa in Islamorada
4 Bedroom Oceanfront Accessible Villa – Capacity 8
4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 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
Featured hotel
Hotel in Islamorada
Alligator reef oceanfront room king
1 bedroom, 1 bathroom
9–14 Aug
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 6 Sept
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
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, 38 reviews
Superhost
Home in Islamorada
Brand-New 4BR Island Home in Central Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
9–16 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, 3.5 bathrooms
23–30 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Marathon
Oceanfront 5BR+Bonus Room •Sunrise Pool Spa•Beach
5 bedrooms, 10 beds, 6 bathrooms
15–22 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews