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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
Featured hotel
Hotel in Tavernier
Standard two bedroom partial ocean view suite
New place to stay, 2 bedrooms, 1 bathroom
17–22 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
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
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
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
6–11 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
6–11 Jul
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
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
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
Home in Key Largo
Home in the keys with pool/boat dock/water view!
3 bedrooms, 4 beds, 2 bathrooms
8–13 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 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
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
Flat in Tavernier
Mockerman Southern Command
4.93 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
Guest favourite
Flat in Tavernier
Welcome to the Pelican Lodge !
4.91 out of 5 average rating, 33 reviews, 2 bedrooms, 4 beds, 2 bathrooms
15–20 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
Guest favourite
Flat in Tavernier
Oceanfront Bliss • Wall-to-Wall Water Views + Pool
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug