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Cheap Holiday Villa and Cottage Deals in Islamorada, FL
Holiday Rentals
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Florida (FL)
Florida Keys
Islamorada
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Internet or Wifi (796)
Air Conditioning (792)
Washer/Dryer (559)
Other outdoor space (555)
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Suitability
Kid friendly (781)
Pet friendly (330)
Smoking allowed (21)
Elder access (6)
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Property type
Holiday Rental House (679)
Condominium/Apartment (135)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (470)
Boat Available (86)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
History of Diving Museum
Florida Keys Brewing Company
Islamorada Brewery & Distillery - MM82
Alligator Reef Light House
Windley Key Fossil Reef Geological State Park
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814 rentals
in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 4
Match:
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Adorable canal front Pool Home in Plantation Key
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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ULTIMATE outdoor living area at this 4/4 canal home with pool!
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Modern Oceanview Paradise at Islamorada
2
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Southern Comfort - Charming oceanfront private oasis!
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
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Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Cancellation Opened for Winter! Remodeled Townhome in Resort..Pool, Beach!!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 7
Match:
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Tranquil One Bedroom Cottage with Pool and Boat Basin
8
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Brand New Home, Resort Location, Ocean View
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Key Lime Cottage in Islamorada
26
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Beautiful house located in the prestigious neighborhood of Port Antigua on a
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Seaside Sanctuary in the Heart of Islamorada
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 8
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"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 12
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Scenic Beachfront Suite w/ Gorgeous Views & Family-Friendly Pool | Free Parking
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Your PRIVATE OCEANFRONT ESTATE awaits! Dive into the Infinity Pool & 150' Beach
14
Holiday Rental House
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5 bedrooms
6 bathrooms
Sleeps 10
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Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Casa Del Pirata | 3 bed / 2 ba Canal Home in Islamorada
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Minutes to Library Beach Park! Onsite Parking & Outdoor Swimming Pool
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Beach Getaway! Outdoor Pool, Free Parking, Near Keys History & Discovery Center
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Best Location in Islamorada!! Beach access - Boat trailer parking!
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 12
Match:
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Escape the cold Work from Home Beach, Pool, Fishing Pier & 2 Kayaks & 2
6
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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15% to 20% OFF LUXURY HOUSE CLOSE TO THE OCEAN IN PORT ANTIGUA
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
Match:
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Islamorada Luxury Waterfront Condo with Boat Slip
12
Condo/Apartment
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Sandy Beach Cove️️ Gated Private Beach Home and Cottage Oasis With Dock
3
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Canal Front Oasis with Private Pool: Your Perfect Waterfront Getaway!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Charming cottage on the Florida Bay in the heart of Islamorada with pool
10
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Beautiful sunsets & water views
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125
3
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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You will love my "Fl Keys Luxury Home"
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
10
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Cozy Cottage in the Heart of Islamorada
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
19
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
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Anglers Reef Islamorada, Bikes,Kayak,Paddle Boards DOCK available-Pool
10
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
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Expansive Ocean views!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Excellent Choice! Pet-friendly Property, Pool, Free Parking Onsite!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 6
Match:
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Luxurious 4-Bedroom Home with Private Pool and Beach Access in Islamorada
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024
Holiday Rental House
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5 bedrooms
8 bathrooms
Sleeps 10
Match:
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Beach Getaway: Room with Access to Pristine Sands | 2 Relaxing Rooms
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
4
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Recently Renovated Luxury Townhome in Islamorada, Florida Keys
3
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
61
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
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2nd Floor Duplex on Gated Bayfront Property
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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FLORIDA KEYS
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Best location in downtown Islamorada. Beach access and boat trailer parking!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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Gulf View Retreat * Bay Harbor
5
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
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