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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
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
14–21 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
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
4.96 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
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
23–28 Aug
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
4.97 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Featured hotel
Hotel in Key Largo
Cottage 2 queen beds with kitchenette
New place to stay, 1 bedroom, 1 bathroom
12–17 Aug
Home in Islamorada
Margaritaville
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Guest favourite
Flat in Tavernier
Oceanfront Bliss • Wall-to-Wall Water Views + Pool
5.0 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Apartment in Tavernier
Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Home in Key Largo
Home in the keys with pool/boat dock/water view!
3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
5.0 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
Superhost
Home in Islamorada
Waterfront / Ocean Access Canal / Kamp Key
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3 bathrooms
22–27 Aug
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
Superhost
Apartment in Islamorada
First Floor Coastal Escape | Restaurant Onsite
1 bedroom, 3 beds, 2 bathrooms
13–18 Jul
Guest favourite
Apartment in Tavernier
Your Happy Place - Oceanfront
4.95 out of 5 average rating, 146 reviews, 2 bedrooms, 4 beds, 2 bathrooms
11–16 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
14–21 Jul
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
4.81 out of 5 average rating, 37 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 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
21–26 Jul