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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
26–31 Jul
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4.8 out of 5 average rating, 90 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
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed, 3 bathrooms
5–10 Jul
New place to stay
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
1–8 Jul
New place to stay
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
Islamorada Bungalow # 5
2 bedrooms, 2 beds, 1 bathroom
6–11 Aug
4.85 out of 5 average rating, 34 reviews
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
4 bedrooms, 5 beds, 4.5 bathrooms
5–12 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 29 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, 24 reviews
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
4.97 out of 5 average rating, 143 reviews
Flat in Key Largo
Key Largo, Florida Bay Townhome! 7/18 -7/25/2026!
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Jul
New place to stay
Superhost
Home in Islamorada
Pineapple Beach
5 bedrooms, 13 beds, 4.5 bathrooms
4–11 Jul
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds, 3 bathrooms
8–15 Aug
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, 109 reviews
Superhost
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds, 5 bathrooms
16–21 Aug
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Featured hotel
Hotel in Islamorada
Studio suite garden view two queen accessible
1 bedroom, 2 queen beds, 1 bathroom
7–12 Aug
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 bathrooms
7–14 Jul
4.92 out of 5 average rating, 24 reviews