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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 private bathroom
1–6 Aug
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4.8 out of 5 average rating, 91 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
24–29 Jul
New place to stay
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
2 bedrooms, 2 beds
17–22 Aug
4.86 out of 5 average rating, 36 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
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds
18–25 Jul
5.0 out of 5 average rating, 24 reviews
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
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
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms
10–17 Jul
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds
8–15 Sept
4.88 out of 5 average rating, 34 reviews
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
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 214 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds
5–12 Sept
New place to stay
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds
30 Aug – 6 Sept
New place to stay
Featured hotel
Hotel in Islamorada
Matacumbe courtyard view room two queens Lanai
1 bedroom, 2 queen beds
4–9 Aug
Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds
18–25 Jul
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Marathon
New Oceanfront +5BR•Sunrise Views•Pool Spa•Beach
5 bedrooms, 10 beds
15–22 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds
24–31 Jul
4.96 out of 5 average rating, 25 reviews