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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 private bathroom
8–15 Aug
,
4.97 out of 5 average rating, 215 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
24–29 Jul
New place to stay
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
9–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
15–22 Sept
5.0 out of 5 average rating, 53 reviews
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms
25 Jul – 1 Aug
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 147 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds
20–25 Oct
5.0 out of 5 average rating, 112 reviews
Luxe
Villa in Islamorada
4 Bedroom Oceanfront Accessible Villa – Capacity 8
4 bedrooms, 5 beds
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4 bedrooms, 4 beds
16–23 Aug
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
9–15 Aug
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Marathon
4BR 3B, Heated Pool & Spa, 60' Dock
4 bedrooms, 7 beds
15–22 Aug
4.95 out of 5 average rating, 106 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds
5–12 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds
7–12 Sept
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds
15–22 Aug
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds
23–30 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds
23–30 Aug
4.95 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
2 bedrooms, 2 beds
7–12 Aug
4.86 out of 5 average rating, 266 reviews