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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 Jul
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4.93 out of 5 average rating, 385 reviews
Home in Islamorada
Margaritaville
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Guest favourite
Home in Islamorada
FL Keys Ocean Front Escape
4.9 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 3 bathrooms
7–14 Jul
Guest favourite
Home in Tavernier
Luxury Treehouse | Spacious Parking |
4.93 out of 5 average rating, 30 reviews, 4 bedrooms, 4 beds, 2 bathrooms
4–9 Apr
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4.96 out of 5 average rating, 136 reviews, 4 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
7–14 Jul
Guest favourite
Apartment in Tavernier
Views for Days • Oceanfront Suite w/ Pool Paradise
4.88 out of 5 average rating, 84 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Home in Key Largo
Home in the keys with pool/boat dock/water view!
3 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
Superhost
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
4.91 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 31 reviews, 3 bedrooms, 3 bathrooms
9–15 Aug
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Jul
Guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 3 bathrooms
18–25 Jul
Guest favourite
Home in Islamorada
Oceanfront community 114 Anglers Reef Islamorada
4.86 out of 5 average rating, 63 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
11–18 Jul
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
4.97 out of 5 average rating, 102 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
4.95 out of 5 average rating, 44 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
4.98 out of 5 average rating, 89 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
22–29 Aug
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
4.92 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
7–14 Jul
Superhost
Home in Key Largo
NEW! CASA LARGO -Golf Cart, 2 Kings 3 Bath, Kayaks
4.95 out of 5 average rating, 37 reviews, 2 bedrooms, 5 beds, 3 bathrooms
20–25 Jul
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
5–12 Aug