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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 Aug
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4.93 out of 5 average rating, 387 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
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
3 bedrooms, 6 beds, 3 bathrooms
7–12 May
4.96 out of 5 average rating, 68 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
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
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds, 2 bathrooms
10–17 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 52 reviews
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 bathrooms
1–8 Aug
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
4 bedrooms, 5 beds, 4.5 bathrooms
14–21 Jul
5.0 out of 5 average rating, 7 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
17–22 Jul
4.91 out of 5 average rating, 34 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
4.8 out of 5 average rating, 50 reviews
Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 1 bathroom
7–12 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
Villa in Islamorada
Islamorada | Maison Residences
4 bedrooms, 5 beds, 6 bathrooms
20–27 Jul
4.92 out of 5 average rating, 12 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 147 reviews
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds, 7.5 bathrooms
8–15 Sept
4.89 out of 5 average rating, 35 reviews
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 bathrooms
14–21 Jul
4.92 out of 5 average rating, 24 reviews
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds, 5 bathrooms
16–21 Aug
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
2–9 Aug
5.0 out of 5 average rating, 11 reviews