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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
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4.98 out of 5 average rating, 60 reviews
Guest favourite
Home in Tavernier
Luxury Treehouse | Spacious Parking |
4 bedrooms, 4 beds, 2 bathrooms
4–9 Apr
4.93 out of 5 average rating, 30 reviews
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Islamorada
FL Keys Ocean Front Escape
2 bedrooms, 2 beds, 3 bathrooms
15–22 Jul
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 136 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–15 Aug
4.97 out of 5 average rating, 33 reviews
Featured hotel
Hotel in Key Largo
Cottage 2 queen beds with kitchenette
1 bedroom, 2 queen beds, 1 bathroom
12–17 Aug
New place to stay
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 103 reviews
Superhost
Home in Islamorada
Islamorada Casa Playa (Beach House)
4 bedrooms, 5 beds, 3 bathrooms
8–13 Aug
Guest favourite
Apartment in Tavernier
Views for Days • Oceanfront Suite w/ Pool Paradise
2 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
4.87 out of 5 average rating, 85 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 75 reviews
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
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 84 reviews
Guest favourite
Flat in Tavernier
Oceanfront Bliss • Wall-to-Wall Water Views + Pool
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Tavernier
Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.81 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 king bed, 1 bathroom
30 May – 4 Jun
4.97 out of 5 average rating, 65 reviews
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