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Islamorada Vacation Rentals and Hotels
HotStays.com features Islamorada vacation rentals, Grassy Key cabin rentals, Lower Keys cottage rentals, Key West holiday villas, Marathon Area bed and breakfast inns, Cudjoe Key discount hotels and Lower Matecumbe Key condo rentals.
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Looking for Islamorada hotels? View all hotels in the Islamorada area.

We have over 600 properties in the Islamorada, Florida area.
Please browse our top 30 properties below
Vacation Rentals in the Islamorada area.
Luxurious Waterfront Condo in Islamorada #2426 From $1,500/week
2 Beds 2.5 Baths Sleeps 6 Condo 4 photos Real-Time Calendar
When you walk in you will feel as if you are right on top the water. Great room has expansive glass doors overlooking the water, queen sleeper, high definition 32-in TV, DVD, stereo, and surround sound. Formal entrance foyer has adjacent third bathroom. Screened terrace overlooking the water is over ...
Canal front Islamorada home in the Keys #913 From $1,400/week
3 Beds 2 Baths Sleeps 6 Condo 4 photos Real-Time Calendar
Three bedroom, two bathroom canal front home in Islamorada. Beautifully furnished with updated appliances. Clear canal with deepwater dockage for boats up to 40 feet. Enjoy a Florida Key vacation at our equipped canal front home! Included: Phone, Air Conditioning, Cable TV, VCR, Microwave, Dishwasher, ...
Quiet Islamorada condo in gated community #912 From $1,800/week
3 Beds 2 Baths Sleeps 6 Condo 4 photos Real-Time Calendar
Three bedroom, two bathroom multi level condo directly on the ocean in Islamorada. Very quiet gated complex with swimming pool, a sandy beach, and fishing pier. The master bedroom is on a separate level with a private balcony and King size bed. The second bedroom holds a queen size bed and the third ...
Beautiful Florida Keys vacation home in Islamorada #895 From $4,000/week, $12,000/month
4 Beds 4 Baths Sleeps 6 House 4 photos Real-Time Calendar
Absolutely beautiful private pool home directly on the ocean in Islamorada. Enjoy your Florida Key vacation at this home which provides you with excellent ocean views, brande new private Oceanfron swimming pool, four bedrooms, four bathrooms, and a beautifully furnished interior. Brand new furniture, ...
Islamorada vacation home in the Keys #894 From $2,500/week
3 Beds 3 Baths Sleeps 8 House 4 photos Real-Time Calendar
A beautiful three bedroom, three bathroom home just a few houses from Tavernier Creek with ocean and bay access. Magnificently furnished with two large bedrooms upstairs and one bedroom with a full bathroom downstairs. Nicely landscaped yard with a swimming pool and boat dockage. All linens and kitchenware ...
Islamorada Florida Keys Waterfront Home #379 From $1,100/week, $2,500/month
3 Beds 2 Baths Sleeps 8 House 4 photos
Enjoy the flexible accomodations of this waterfront home. Three bedroom and 2 bath split level home in Islamorada with wide canal and tropical setting offers great access to the bay and ocean. Upstairs sleeps up to 8 with 2 bedroom, 1 bath, living room with sofa bed, dining area, and full kitchen. ...
Vacation Rentals in the Islamorada/Long Key area. (13 miles away)
Beautiful Florida Key vacation get away #1152 From $2,295/month
2 Beds 1.5 Baths Sleeps 6 Townhouse 15 photos
This beautiful Long Key townhouse is centrally located between Islamorada and Marathon. You will want to come back to this Florida get away year after year. Equipped with two bedrooms, one and a ½ bathrooms and three large screened balconies with ocean views. Located on beautifully maintained grounds ...
Vacation Rentals in the Islamorada/Key Largo area. (20 miles away)
OCEANSIDE POOL HOME W/ DOCKAGE FOR A YACHT. #2182 From $1,500/week
4 Beds 3.5 Baths Sleeps 13 House 17 photos Real-Time Calendar Pet Friendly
Our summer home is a true Paradise, It has a resort like feel to it, a rock waterfall leads right into the heated pool, perfect for a swim, day or night. Enjoy a cool drink in our tiki hut with a complete working bar, or fish right off our 80 foot dock over looking the water.Big enough for a yacht. Want ...
Tropical Stilt House, Key Largo, Florida #338
4 Beds 2 Baths Sleeps 10 House 13 photos Real-Time Calendar
Tropical Stilt Home in Key Largo, Florida. Clean, comfortable home sleeps 2-11 comfortably. Located steps away from the open waters of Florida Bay. Rent all or a portion of this beautiful home at reasonable rates. **************************************************************************************************** YOU ...
"PENTHOUSE BEAUTY",PVT BOAT SLIP,TENNIS ,& MORE #1501 From $975/week, $2,700/month
2 Beds 1.5 Baths Sleeps 4-6 Condo 9 photos Real-Time Calendar
This Penthouse Beauty ,offers unobstructed views of the sunsets, the stars, and of course, our gorgeous bay. For our guests, we have added an electric barbeque grill on our screened-in balcony, as well as a barbeque by the bay at our great roof overhead picnic area. PRISTINE; IMMUCULATE; PRIVATE; ...
Key Largo villa w/ 2BR/2BA sleeps 6 comfortably #1325
2 Beds 2 Baths Sleeps 6 Villa 4 photos
Imagine sunbathing on the white sandy beach, breathtaking sunsets, butterfly/bird/manatee watching and enjoying the sights of our local Island life. Enjoy it all at our Key Largo villa with two bedrooms and two bathrooms. Home is equipped and can sleep up to six comfortably. Beautiful Key Largo beachfront ...
Bring your boat to this Alamar on the bay cottage #1321
2 Beds 2 Baths Sleeps 4 Cottage 4 photos
Beautiful Key Largo beachfront cottage located in a lush tropical garden with spectacular bay views and sunsets. Equipped with two bedrooms, two bathrooms and sleeps up to four guests comfortably. Key Largo Alamar located in a tropical setting on the open water of the Florida Bay on approximately one ...
Bayfront Beach House with Sandy Beach #1312 From $2,500/week
4 Beds 3 Baths Sleeps 10 House 4 photos
Beautiful Key Largo beachfront home located in a lush tropical garden with spectacular bay views and sunsets. Key Largo Alamar located in a tropical setting on the open water of the Florida Bay on approximately one and a half lush acres. Fully equipped home with four bedroom, three baths. Sunbathing ...
Kawama Yacht Club in Key Largo unit 503. #1184 From $895/week
2 Beds 2 Baths Sleeps 8 Condo 4 photos
The Kawama Yacht Club is your escape route to the Florida Keys, only one hour from Miami. Situated at mile marker 100 on the Atlantic Ocean, this gated community offers all you need for a relaxing vacation or getaway. Enjoy the panoramic view this fifth story unit has to offer of the Atlantic Ocean ...
Key Largo townhouse overlooking Blackwater Sound #1173 From $895/week
2 Beds 1.5 Baths Sleeps 6 Townhouse 4 photos
This Moon Bay vacation rental overlooks Blackwater Sound and includes a private boat slip which accommodates up to a 30' vessel. Each bedroom has its own private balcony with water views. There is also a screened patio off the Living Room overlooking the water. Master has a King bed, Guest has a Queen, ...
Superb vacation condo in Key Largo #1172 From $895/week
2 Beds 1.5 Baths Sleeps 2-6 Condo 4 photos
This Key Largo vacation condo contains a new technology convection oven, mirrored wall in living room, extra sitting room, jacuzzi tub in master bathroom, covered parking space, boat slip, new furnishings including King bed in the Master bedroom, Queen bed in the guest bedroom, full sleeper sofa in the ...
Very nice Moon Bay condo in Key Largo #1168 From $895/week
2 Beds 1.5 Baths Sleeps 2-6 Condo 4 photos
Moon Bay located in beautiful Key Largo is where you will find this precious condo. Fully equipped with a remodeled kitchen, three TVs, two VCRs, stereo, dishes, cookware, utensils, blender, toaster, toaster oven, coffee maker, coffee grinder, iron & ironing board, linens, towels, and almost everything ...
Key Largo condo near great diving and snorkeling #1162 From $1,095/week, $3,495/month
2 Beds 1.5 Baths Sleeps 2-6 Condo 4 photos
Moon Bay Condo is in the dive capital of the world - Key Largo, Florida. Moon Bay is located only one mile north of the famous John Pennekamp Coral Reef State Park and is just a short boat ride from diving and snorkeling the Spiegel Grove! The Spiegel Grove is a 510 foot ship - the largest ever sunk ...
Great vacation condo in Key Largo w/ big screen TV #1159 From $795/week, $2,800/month
2 Beds 1 Baths Sleeps 4-6 Condo 4 photos
Located at mile marker 104 in the dive capital of the world – Key Largo, FL. This vacation condo is beautiful and fully equipped with 3 TVs, (one is a Big Screen) 2 DVD players, VCR, VHS Video Library, surround sound, stereo, dishes, cookware, utensils, linens, towels. Relax on the large, private, screened ...
Attractive Key Largo condo near snorkeling #1156 From $995/week
2 Beds 1.5 Baths Sleeps 2-6 Condo 4 photos
Moon Bay Condo is in the dive capital of the world, beautiful Key Largo, Florida. On the Bay, sleeps up to 6 maximum and located approximately 1 mile north of the famous John Pennekamp Coral Reef State Park & is just a short boat ride from diving and snorkeling the Spiegel Grove! The Spiegel Grove ...
Spacious Sexton cove mobile home in Key Largo #1149 From $2,100/month
3 Beds 1.5 Baths Sleeps 6 House 4 photos
This is the one; you'll want to return each season so book now before it's gone! Just posted and will not last long! Single family mobile home located in Sexton Cove of Key Largo at mile marker 106 in Key Largo on the bayside. Bay views from the back. Dock your boat just steps from the back door. Three ...
Cute Key Largo mobile home with private boat ramp #1148 From $1,900/month
2 Beds 1.5 Baths Sleeps 4 House 4 photos
This cute 2 bedroom, 1.5 bathroom Key Largo mobile home sits on a nice canal with direct access to Blackwater Sound. Convenient to Adams Cut, and John Pennekamp Coral Reef State Park. Master bedroom has a Queen bed; guest room has a twin bed. Nicely furnished and fully equipped. Central AC, Washer ...
Oceanside waterfront Key Largo stilt house #1147 From $2,700/month
2 Beds 2 Baths Sleeps 4 House 4 photos
This immaculate two bedroom, two bathroom stilt house in Key Largo sits on a large, waterfront, fenced lot on a dead end street. Includes beautiful water views from the large screened patio and is perfectly situated in a classified area. The canal has direct access to the Atlantic Ocean (Bridge and ...
Beautiful Moon Bay condo with great bay views #927 From $1,000/week, $3,400/month
3 Beds 2.5 Baths Sleeps 6-9 Condo 4 photos Real-Time Calendar
This is a beautiful furnished condo with three bedrooms and two and a half bathrooms. Enjoy the great views of the pool and the bay with dockage included. All linens and kitchenware are provided. All you need to do is bring yourself and enjoy the waterfront living in the Florida Keys. Sleeps up to ...
Fantastic waterfront Key Largo vacation home #896 From $1,600/week, $4,800/month
4 Beds 3 Baths Sleeps 9 House 4 photos
Cheerful and bright Key Largo home with lots of windows and sliding glass doors. This house has a large screened in porch with a gas grill, great for enjoying the sunsets and evening breezes. There is a great dock to see the regularly visiting manatees or to enjoy a day of fishing on. Only minutes ...
Beautiful Waterfront Property in Key Largo! #353 From $2,900/month
3 Beds 2 Baths Sleeps 6 House 4 photos
This beautiful custom colonial style home is the ideal home to stay in when visiting Key Largo. This lovely home is located right on a crystal clear water way with access to Key Largo Marine Sanctuary, and the ocean! In a matter of minutes you can be swimming, dining, snorkeling, shopping, and feeling ...
Key Largo Home w/ Boat Dock & Ocean Access #339 From $1,500/month
3 Beds 2 Baths Sleeps 6 House 4 photos Real-Time Calendar
Pelican by The Bay (Key Largo, Fl) This rental property is located in Key Largo, Florida, mile marker 106 in an open canal that leads into Sexton Cove/Black Water Sound. Close proximity to John Pennincamp National Park and water access to the ocean. Very nicely furnished with 3 bedrooms / 2 Baths. ...
Vacation Rentals in the Islamorada/Marathon area. (28 miles away)
Florida Keys Vacation Rentals– Atlantic Breezes #1682
2-4 Beds 2.5 Baths Sleeps 1-12 Condo 9 photos Pet Friendly
Private Waterfront setting with 50' Dock, Hot Tub, Sun Deck, Tiki Hut & Hammock- Marathon - Marathon, Florida Condo Rental 2 LARGE Luxury Waterfront condos (part of a 2 unit privately owned complex) conveniently located adjacent to each other on Sombrero Beach Road in the Florida Keys! You ...
Fantastic 2BR/2BA Marathon condo - pets welcome #1160 From $995/week, $2,700/month
2 Beds 2 Baths Sleeps 2-6 Condo 4 photos Pet Friendly
Just minutes by boat to the Atlantic or Gulf, fantastic location! We have multiple units at this complex making it convenient for large families. This 2 bedroom, 2 full bathroom, ground floor unit in Marathon comes fully furnished & equipped. King bed in the Master, 2 twin beds in the Guest, Sleeper ...
Condo in great vacation area near Coco Plum beach #1157 From $750/week, $2,100/month
1 Beds 1.5 Baths Sleeps 1-4 Condo 4 photos Pet Friendly
In a perfect location just minutes by boat to the Atlantic Ocean or Gulf! We have multiple units at this complex making it convenient for large families. This 1 bedroom, 1.5 bathrooms, ground floor unit is very clean and comes fully furnished & equipped. Screened Patio just steps from the boat ...
We have over 600 properties in the Islamorada, Florida area.
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