Top 50 Vacation Rentals Islamorada (Florida) 2018

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Amara Cay Resort
110br 3-star Hotel
110 Bedrooms
Parking,
Pool,
Wifi
- Details
Description
Get an overview of this hotelWaterfront hotel with an outdoor pool Location Nestled on the beach, this Islamorada hotel is within 3 mi (5 km) of Bud n' Mary's Dive Center, Lignumvitae Key Botanical State Park, and Hurricane Monument. History of Diving Museum is 3.1 mi (5 km) away. Hotel Features At Amara Cay Resort, spend the day on the private sand beach where you can enjoy snorkeling. Then return for a meal at one of the hotel's 2 restaurants. Room Amenities All 110...
Amenities
Parking
Pool
Wifi
Additional info
Bedrooms:110
Rating Overall Score81%
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Nice
Coconut Cove Resort & Marina
20br 2-star Hotel
20 Bedrooms
Breakfast,
Gym,
Parking,
Pets OK,
Pool,
Wifi
- Details
Description
Property Location Located in Islamorada, Coconut Cove Resort and Marina is on the Strip and minutes from Theater of the Sea on Islamorada and Windley Key Fossil Reef Geological State Park. This hotel is within the vicinity of Hurricane Monument and Bud n Marys Dive Center.Rooms Make yourself at home in one of the 20 air-conditioned rooms featuring LCD televisions. Rooms have private balconies. Cable television is provided for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and...
Amenities
Breakfast
Gym
Parking
Pets OK
Pool
Wifi
Additional info
Bedrooms:20
Rating Overall Score78%
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Nice
Sands of Islamorada
9br 2-star Hotel
9 Bedrooms
Parking,
Pets OK,
Pool,
Wifi
- Details
Description
Get an overview of this hotelSuburban hotel in Islamorada with free parking Location Situated by the sea, this hotel is 0.3 mi (0.5 km) from Bud n' Mary's Dive Center and within 3 mi (5 km) of Hurricane Monument and Lignumvitae Key Botanical State Park. History of Diving Museum is 3 mi (4.8 km) away. Hotel Features This hotel features an outdoor pool, laundry facilities, and free self parking. WiFi in public areas is free. Room Amenities All rooms are individually decorated and offer...
Amenities
Parking
Pets OK
Pool
Wifi
Additional info
Bedrooms:9
Rating Overall Score78%
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Good
Islander Resort, a Guy Harvey Outpost
114br 3-star Hotel
114 Bedrooms
Gym,
Parking,
Pets OK,
Pool,
Wifi
- Details
Description
Get an overview of this hotel3-star resort with pools and private beach Location Nestled on the beach, this Islamorada resort is within 1 mi (2 km) of Hurricane Monument and History of Diving Museum. Windley Key Fossil Reef Geological State Park and Bud n' Mary's Dive Center are also within 3 mi (5 km). Resort Features At Islander Resort, relax by one of the 2 outdoor swimming pools or spend the day at the private sand beach where you can enjoy kayaking. Room...
Amenities
Gym
Parking
Pets OK
Pool
Wifi
Additional info
Bedrooms:114
Rating Overall Score81%
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Nice
Postcard Inn Beach Resort & Marina
143br 3-star Hotel
143 Bedrooms
Wifi
- Details
Description
Property Location When you stay at Postcard Inn at Holiday Isle in Islamorada, youll be on the waterfront and convenient to Theater of the Sea on Islamorada and Windley Key Fossil Reef Geological State Park. This beach resort is within the vicinity of Hurricane Monument and Bud n Marys Dive Center.Rooms Make yourself at home in one of the 150 air-conditioned rooms featuring plasma televisions. Complimentary high-speed (wired) Internet access keeps you connected, and cable programming is available for your...
Amenities
Wifi
Additional info
Bedrooms:143
Rating Overall Score74%
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Good
Cheeca Lodge & Spa
214br 4-star Resort
214 Bedrooms
Breakfast,
Gym,
Parking,
Pool,
Wifi
Unique
- Details
Description
Property Location With a stay at Cheeca Lodge Spa in Islamorada, youll be convenient to Hurricane Monument and History of Diving Museum. This 4-star resort is within the vicinity of Windley Key Fossil Reef Geological State Park and Founders Park.Rooms Make yourself at home in one of the 212 air-conditioned rooms featuring refrigerators and DVD players. Rooms have private balconies. Plasma televisions along with CD players are provided for your entertainment. Bathrooms feature bathtubs or showers, makeup/shaving mirrors, and...
Amenities
Breakfast
Gym
Parking
Pool
Wifi
Additional info
Bedrooms:214
Rating Overall Score86%
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Good
Drop Anchor Resort Motel, IslamoradaDrop Anchor Resort
18br 3-star Hotel
18 Bedrooms
Parking,
Pool,
Wifi
- Details
Description
Property Location With a stay at Drop Anchor Resort and Marina in Islamorada, youll be on the beach and minutes from Windley Key Fossil Reef Geological State Park, and close to Theater of the Sea on Islamorada. This beach hotel is within the vicinity of Hurricane Monument and Bud n Marys Dive Center.Rooms Make yourself at home in one of the 18 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for...
Amenities
Parking
Pool
Wifi
Additional info
Bedrooms:18
Rating Overall Score81%
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Nice
La Siesta Resort & Marina
52br 3-star Hotel
52 Bedrooms
Parking,
Wifi
- Details
Description
Property Location When you stay at La Siesta Resort Marina in Islamorada, youll be on the beach and convenient to Bud n Marys Dive Center and Hurricane Monument. This beach resort is within the region of Windley Key Fossil Reef Geological State Park and Founders Park.Rooms Make yourself at home in one of the 54 individually decorated guestrooms, featuring kitchens with refrigerators and stovetops. Rooms have private balconies. Complimentary wireless Internet access keeps you connected, and cable programming is...
Amenities
Parking
Wifi
Additional info
Bedrooms:52
Rating Overall Score77%
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Nice
Pelican Cove Resort & Marina, IslamoradaPelican Cove Resort & Marina
63br 3-star Hotel
63 Bedrooms
Parking,
Pool,
Wifi
- Details
Description
The resort offers guests a total of 63 rooms. Amenities include a safe. Wireless internet access is available to travellers in the public areas. Among the culinary options available at the holiday complex are a restaurant, a breakfast room, a café and a bar. Those arriving in their own vehicles can leave them in the car park of the complex. Additional services include a childcare service, car hire and a laundry service. Active guests can make use of the bicycle...
Amenities
Parking
Pool
Wifi
Additional info
Bedrooms:63
Rating Overall Score75%
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Nice
Chesapeake Beach Resort
65br 3-star Resort
65 Bedrooms
Parking,
Pets OK,
Pool,
Wifi
Unique
- Details
Description
The Chesapeake has 65 spacious units. Oceanfront guest rooms and suites have spectacular views of the Atlantic Ocean. Individually appointed villas with fully equipped kitchens, range from single room efficiencies to one and two bedroom units. Garden view motel units with screened porches overlook the tennis court. PLEASE NOTE: There is a resort fee of $18.00 (including applicable tax) per night, per room that is payable directly to property....
Amenities
Parking
Pets OK
Pool
Wifi
Additional info
Bedrooms:65
Rating Overall Score71%
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Good
Pines & Palms Resort
23br 3-star Hotel
23 Bedrooms
Parking,
Pool
- Details
Description
Cottages, suites and duplexes in a tropical setting on the Atlantic Ocean in Islamorada. Each one-bedroom unit comes with a king or queen bed, a fully equipped kitchen, living room with sofa bed and patio or balcony. Tastefully decorated with tropical style furniture. Two and three bedroom units also available. Free reserved boat dockage, ramp and trailer storage for boats up to about 25 feet depending on draft. Call for availability. House guide for fishing, diving, eco tour and sunset...
Amenities
Parking
Pool
Additional info
Bedrooms:23
Rating Overall Score85%
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Excellent
Sailboat - Swim/Snorkel/Kayak
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space Have you ever slept floating? You can enjoy this experience on our permanently docked 1964 Columbia 24" sailboat. The boat provides the perfect accommodations for one or two young people (perfect "crash pad" for the 20- and 30-somethings!). The boat has only two rooms: a sitting area (quite small, but it's cozy!), and a double-sized bed sleeping with (with a 24" wide entrance). Limited storage and counter space, but no cooking facilities or...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Efficiency - Snorkel, Swim, Kayak
1br Other
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space The Efficiency is constantly undergoing upgrades and renovation without losing it's old-style Keys charm and decor. The space consists of, as you walk through the front door which faces the beautiful Gulf of Mexico: A small sitting room with couch, coffee table and TV, followed by a queen bed and fully equipped kitchen and sizable restroom (although the shower stall is narrow). Full water view, private patio table/chairs and gas grill provided. A little quirky...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Good
La Jolla Resort
21br 2-star Inn
21 Bedrooms
Parking,
Pool,
Wifi
- Details
Description
Get an overview of this hotelWaterfront hotel with an outdoor pool Location Located in Islamorada, this beachfront hotel is in the city center and within 1 mi (2 km) of History of Diving Museum and Hurricane Monument. Windley Key Fossil Reef Geological State Park and Theater of the Sea are also within 3 mi (5 km). Hotel Features Guests at this beach hotel will appreciate convenient onsite amenities such as barbecue grills and a picnic area. Room Amenities All rooms are individually decorated and...
Amenities
Parking
Pool
Wifi
Additional info
Bedrooms:21
Rating Overall Score84%
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Good
Casa Morada
16br 4-star Hotel
16 Bedrooms
Breakfast,
Parking,
Pool,
Wifi
- Details
Description
Get an overview of this hotelAdults-only resort with free breakfast and outdoor pool Location Situated near the bay, this resort is within 1 mi (2 km) of History of Diving Museum and Hurricane Monument. Theater of the Sea and Bud n' Mary's Dive Center are also within 3 mi (5 km). Resort Features Along with an outdoor pool, this resort has a bar/lounge and a poolside bar. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Additionally,...
Amenities
Breakfast
Parking
Pool
Wifi
Additional info
Bedrooms:16
Rating Overall Score89%
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Excellent
Cottage - Waterview, Kayak, Snorkel
Cottage
1 Bathroom
3 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space Very roomy, the Cottage is set up like a studio apartment and has one queen sized bed and a couch/futon. It also has a private restroom and fully equipped kitchen with dinette set (or perhaps dine al fresco on a private patio?). Large sliding glass doors give you a beautiful view of the Gulf of Mexico without even stepping outside your room. A perfect, private retreat for couples. Maximum occupancy: 3 Guest Access Private patio with...
Amenities
Wifi
Pets OK
Parking
Additional info
Sleeps:3
Bathrooms:1
Rating Overall Score100%
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Excellent
House - Waterview, Kayak, Snorkel
1br Home/Apartment
1 Bedroom
1 Bathroom
6 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space "The House" is actually a very large, spacious apartment. There is one large private bedroom with a king bed, a full kitchen with large breakfast bar, and dining area. In the main living area there is sectional seating (with recliners!) and coffee table. Behind the living area (but in the same space) is another king-sized bed and a pull-out futon. Very roomy. Maximum occupancy: 6 Guest Access Personal patio with table, chairs and barbecue....
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Good
Islander Bayside
25br 3.7-star Hotel
25 Bedrooms
Pool
- Details
Description
Get an overview of this hotelWaterfront condos with kitchens and furnished balconies Location This family-friendly Islamorada condo building is located on the waterfront, within 2 mi (3 km) of Hurricane Monument and Bud n' Mary's Dive Center. History of Diving Museum is 1.9 mi (3 km) away. Property Features An outdoor pool, concierge services, and dry cleaning are available at this condo building. Free WiFi in public areas and free self parking are also provided. Additionally, free newspapers, wedding services, and barbecue grills...
Amenities
Pool
Additional info
Bedrooms:25
Rating Overall Score88%
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Excellent
360 DEGREE WATERVIEW HOUSEBOAT
1br Boat
1 Bedroom
1 Bathroom
2 Sleeps
Wifi
- Details
Description
The Space After 2 years and 200 reservations posting my Houseboats on airbnb, I am very great full for the ones that appreciated life off shore, but decided that anyone is not ready for a Salty get away, sold all my houseboats and took a long break , now I am back with a green powered Houseboat. Solar panels supply the energy for refrigerator, freezer, TV, access to WIFI, full kitchen, outdoor grill, bathroom with...
Amenities
Wifi
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip
3br Boat
3 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Wifi
- Details
Description
Please look at the (video icon) in the picture to view the video of the homes location. A tropical boater's and angler's paradise, this Key West styled luxury villa in Islamorada boasts the best fishing in South Florida. With tangerine sunsets glistening across the calm ocean waters, an afternoon boat ride is as easy as walking out your back door. Dolphin and turtles are common. Deep water access, boat dock, nearby marina with fuel, bait and...
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score99%
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Excellent
Keys home in Anglers Reef with ocean view, dock, community pool & private beach
2br Home/Apartment
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home's...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score99%
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Excellent
Bright & Clean Tropical Bungalow with Heated Pool, Bikes, Grill, and free WiFi
2br Bungalow
2 Bedrooms
1 Bathroom
4 Sleeps
Parking,
Wifi
- Details
Description
*** SPECIAL NOTE *** To all of our guests and friends who have reached out to us after Hurricane Irma - THANK YOU. Our bungalow made it through the storm, and the clean up is complete. Our pool is sparkling clean (now heated!), and we've planted many new trees and plants. The Islamorada residents and businesses have done an amazing job of cleaning up and beautifying the island. With warm regards, Bill & Maggie This adorable little bungalow, renovated in 2015, is clean...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score99%
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Excellent
Keys home in Anglers Reef with ocean view, dock, community pool & private beach
2br Home/Apartment
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home's...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score99%
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Good
The Caribbean Resort at Sea Isle, IslamoradaThe Caribbean Resort at Sea Isle
13br 3.5-star Hotel
13 Bedrooms
Parking,
Wifi
- Details
Description
Get an overview of this hotelWaterfront resort with marina and outdoor pool Location Situated on the waterfront, this resort is 0.7 mi (1.1 km) from Hurricane Monument and within 3 mi (5 km) of History of Diving Museum and Bud n' Mary's Dive Center. Theater of the Sea is 3 mi (4.8 km) away. Resort Features Along with a marina, this resort has an outdoor pool and a spa tub. Free WiFi in public areas and free self parking are also provided. Additionally,...
Amenities
Parking
Wifi
Additional info
Bedrooms:13
Rating Overall Score88%
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Excellent
Anglers Reef 140 Truly OceanFRONT Villa 3BR 2.5 Bath - Panoramic views In & Out!
3br Villa
3 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Wifi
- Details
Description
**See our many REVIEWS, which tell it all about ANGLERS REEF 140! Our home is known as "Aqua Vistas" and for good reason: THE OCEAN VIEWS DON'T GET ANY BETTER THAN FROM THIS HOME - inside and out on the spacious decks! We are one of only 5 truly OceanFRONT homes in Anglers Reef -- and the only one of those 5 that rents. We are also one of the very few with LARGE WRAPAROUND DECKS ON BOTH...
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
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Excellent
KEYS- ANGLERS REEF, ISLAMORADA- OCEAN VIEWS, POOL, SLIPS, BEACH, FAMILY-FRIENDLY
2br Other
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
COMMUNITY Angler's Reef is Islamorada’s premier gated, oceanfront community of 52 private, single-family homes, located at mile marker 85 on Windley Key, offers lushly landscaped grounds and “Bahamian conch cottages”. It's a unique and relaxing environment. Swim in the oceanfront resort-style pool, a refreshing 87degrees year-round. Enjoy a sunrise or sun-bathe on the east beach. Launch our two complimentary sit-in kayaks from the west beach for an afternoon of swimming and socializing at the famous “Holiday Isles...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score97%
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Excellent
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
2br Other
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
NOTE! We had no damage from Hurricane Irma. Way south in the Lower Keys, there was significant damage. But not in Islamorada. It's still paradise as usual. Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many kid friendly features. Outfitted with his and her...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score96%
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Excellent
Island Yacht Adventures
1br Boat
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Breakfast,
Parking
- Details
Description
The Space We are docked at the famous Lorelei restaurant and tiki bar in the beautiful island of Islamorada, Florida keys,known as the fishing capital of the world and great diving on her beautiful reefs. Sunsets are breathtaking! Your stateroom is forward with its on separate shower to port and separate head to starboard. The stateroom is very comfortable with a queen island bed and separate air-condition control. Saloon is very spacious with lots of window to view the water. The...
Amenities
Wifi
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
SPECIAL OCTOBER RATE Gated Community with Pool. Private Boat Slip available
2br Boat
2 Bedrooms
3 Bathrooms
5 Sleeps
Parking,
Wifi
- Details
Description
Fully Licensed Islamorada home set in gated community with heated swimming pool and privately owned Boat Slip which is available to rent. (Not all houses at Anglers Reef come with a Boat Slip) Our beautiful house has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances, including gas BBQ. Open porches and balconies, rich hard wood floors, dining room with ample seating, tasteful décor and fully furnished rooms. A truly unique place to stay in the...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:5
Bathrooms:3
Rating Overall Score99%
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Excellent
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
4br Boat
4 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Wifi
- Details
Description
Angler's Reef is located at MM84.4 in Islamorada, the heart of the Florida Keys. Our gated community is made up of 52 luxury waterfront villas accompanied by a boat basin with 36 slips, and a pool among the many amenities. Enjoy the expansive views and ocean breezes from the wrap around balconies on the first and second story. Chef's kitchen with top of the line appliances, granite counters, eat at bar and extra beverage/bar fridge. Kitchen is fully stocked with cookware,...
Amenities
Parking
Wifi
Additional info
Bedrooms:4
Sleeps:8
Bathrooms:3
Rating Overall Score99%
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Excellent
Islamorada Home In Paradise - NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY
2br Country House
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY!!! This beautiful villa, 106 Anglers Reef, is fully licensed by the Village of Islamorada for Vacation Rentals, license # VR-224. It is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean. The detached villas are set along quaint streets and walking paths, with combine solid craftsmanship...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score98%
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Excellent
Welcome to Paradise "Sandbar Bungalow Villa" @ Anglers Reef
2br Country House
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
COMPLETEY UPDATED 2018! This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home’s boat slip is available for rent with a deep channel out to the Atlantic. Or launch your kayak from the private beach (kayak rentals available for drop-off). Wonderful, cozy home...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score95%
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Excellent
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
2br Resort
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of stunning private beach. Protected deep water marina with a deep channel out to the Atlantic. Brand new Ocean Kayak 12 foot Tandem available for your use. Launch...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score98%
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Excellent
Key West Style, Oceanfront Anglers Reef, Pool, Boat Slip inc., 2 Master Bed
2br Boat
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
“Palm La Mar - Luxury Vacation Rental” Oceanfront Community of Anglers Reef, gated, detached homes, heated pool, 2 beaches. Non-smoking, no pets. Smoking is permitted on beaches. Boat slip included for up to 31 foot boat, fish cleaning stations, fresh water, private marina on property. Not all homes at Anglers Reef have a boat slip. This boat slip offers the best accessibility for boats small and large. Easy to maneuver and accommodating for large vessels. 2 master bedroom suites with king size...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score97%
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Excellent
FLAKEYS BED & BEER VR 284
2br Bed & Breakfast
2 Bedrooms
1 Bathroom
6 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space Super Keezy and very clean! Directly across the street from Morada Bay full moon party's, on the same street as Third Thursday Art Walks, Islamorada Seafood Festival and other festivals. Watch fireworks from your private balcony New Years night and Full Moon Parties. You cant beat this spot. Walk across the street to World Wide Sportsman Marina and pick from dozens of local guides to take you fishing or eco-tours. Islamorada is the sport fishing capital of the world, don't...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Excellent
Angler's Reef W Boat Slip!
2br Boat
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
Welcome to Anglers Reef, a quiet upscale gated community consisting of 52 single family homes built in the traditional Key West Conch and British West Indies cottage styles. This resort style community is located at mile marker 85 in Islamorada and is situated directly on the Atlantic Ocean with fantastic views. The community is beautifully landscaped and has a large community pool (heated year-round) that overlooks the ocean! The community also offers a marina and two fantastic...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score98%
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Excellent
Nature Lovers Houseboat in the Keys
2br Boat
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space For a fun and unusual place to stay and savor life aboard a houseboat safely docked at a small private yacht club, this 38 foot Holiday Mansion will suit you. The houseboat has 2 interior levels which produce about 600 square feet of living space. Wraparound windows permit a 360 degree view. Side windows have mini blinds or curtains. The two rooftop decks are ideal for watching birds and manatees while you sip margaritas made in the galley's...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Good
2 bedroom yacht in the water at Islamorada
2br Boat
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
This is a rare opportunity to live the life of a boater. Stay on our boat, enjoy sunsets from the top deck, and enjoy staying at one of the best neighborhood in Islamorada. Our location is close to nice restaurants, activities and night life in Islamorada. We can charter the 42' yacht for you for a romantic getaway or snorkeling adventure....
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Excellent
Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
2br Home/Apartment
2 Bedrooms
3 Bathrooms
5 Sleeps
Parking,
Wifi
- Details
Description
ANGLERS REEF is quiet oceanfront community of Key West inspired homes, streets, and walking paths, that wind through a quaint village-style retreat. Located at Mile Marker 85 by Theater of the Sea, Windley Key Geographical Site, Snake Creek Marina & some of the best bars and restaurants in Islamorada. GREAT LOCATION The house is in a quiet section of the community, away from the highway and just 2 homes from the ocean. Our porches, are shaded, and face...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:5
Bathrooms:3
Rating Overall Score99%
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Excellent
Anglers Reef Home Boat Dock Available
2br Boat
2 Bedrooms
3 Bathrooms
5 Sleeps
Parking,
Wifi
- Details
Description
Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -is one of the best kept secrets in the Keys. View my other Anglers Reef Property: vrbo 677953 Florida State Licensed Single Family Dwelling No. DWE5403660. City of Islamorada Vacation Rental License No. VR-216 Upstairs master bedroom has new king size bed; second master bedroom has queen size bed and full size sleeper sofa...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:5
Bathrooms:3
Rating Overall Score99%
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Excellent
WATERFRONT COTTAGE GREAT RATES !
1br Cottage
1 Bedroom
1 Bathroom
2 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Enjoy the peace and privacy of the large, natural waters edge property with the convenience of being minutes away from some of the best dining and outdoor activities in the Florida Keys. Relax in our 1940's 'Old Florida' Keys style cottage, recently updated, while still maintaining its original old Keys look and feel ~ Private large property yet within walking distance to world famous Lorelei Cabana for sunset cocktails ~ or just hang out and enjoy the...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
2br Home/Apartment
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Reef is a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score99%
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Excellent
Happy Tarpon House on Florida Bay:Private Heated Pool - Private Boat Dock - Fun!
3br Boat
3 Bedrooms
4 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
Happy Tarpon - the best of the Florida Keys. The best of Islamorada! Enjoy privacy in this recently renovated home in the heart of Islamorada. It is furnished for easy tropical living inside and out. We have a heated pool, protected deep-water boat dock and magnificent sunsets looking across the Florida Bay. The boat dock holds up to a 25-foot boat in at the protected canal. It is a great place to be...
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:4
Rating Overall Score100%
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Excellent
PRIVATE 1/1 IN ISLAMORADA-OPEN FOR THE SUMMER!
1br Other
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space This 1 bed/1 bath guest quarters within luxury home offers guests private and spacious indoor AND outdoor living space. Large screened in porch and small balcony provide seating areas and BBQ/wet bar for great outdoor and indoor, Keys living. Perfect location walking distance to Founders Park and Beach with beach, pool, tennis courts and marina easily accessible to all guests. Interior and exterior living space is newly furnished and decorated for guest comfort and includes Cable...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Good
The Moorings Village
18br Hotel
18 Bedrooms
Gym,
Parking,
Pool,
Wifi
- Details
Description
Get an overview of this hotelVilla with private beach, full-service spa Location Located in Islamorada, this beachfront villa is in the entertainment district and within 3 mi (5 km) of Hurricane Monument, History of Diving Museum, and Bud n' Mary's Dive Center. Windley Key Fossil Reef Geological State Park and Plantation Key are also within 6 mi (10 km). Property Features Catch some rays on The Moorings Village's private white sand beach, pamper yourself at the full-service spa, or enjoy yoga. Room Amenities All...
Amenities
Gym
Parking
Pool
Wifi
Additional info
Bedrooms:18
Rating Overall Score89%
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Excellent
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
2br Home/Apartment
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of stunning private beach. Protected deep water marina with a deep channel out to the Atlantic. Brand new Ocean Kayak 12 foot Tandem available for your use. Launch kayak from the private beach and try your luck...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score96%
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Excellent
Anglers Reef Islamorada 2/2.5 great family home oceanfront community
2br Home/Apartment
2 Bedrooms
3 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
Welcome to your vacation! This newer well built colonial style Villa has 2 bedrooms, 2.5 baths, and sleeps 4 adults and 2 children comfortably. Located in a beautiful gated community framed by mangroves and the ocean, our home in Anglers Reef is everything you're looking for in the picturesque beauty of the Florida Keys making it the perfect backdrop for your vacation memories. Dockage available upon request for additional fee. This is the most family friendly upscale community you will find...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:3
Rating Overall Score98%
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Excellent
Islamorada Oceanfront Estate | Private Pool, Beach & Dock | Your Hammock awaits
4br Estate
4 Bedrooms
5 Bathrooms
12 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Islamorada Rental License: VR - 065 4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dock Separate upstairs Den area sleeps up to 6 kids. * 7 Day minimum rental - Saturday to Saturday * SORRY NO WEDDINGS OR LARGE EVENTS ALLOWED Max 8 adults + 4 children Standard rate $6200 Low Season Rates 2nd Sat. in Sept. to Nov 30th $5200 Thanksgiving...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:4
Sleeps:12
Bathrooms:5
Rating Overall Score96%
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Excellent
Private 150 Ft Oceanfront 2 Acre Millionaire Row Estate Saltwater Pool Spa Dock
4br Estate
4 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
San Rock is secluded ocean front home with spectacular views of open water. Breathtaking views of the Atlantic Ocean. Beautiful 4 Bedroom 3 Bath Home situated on over 2.5 acre secluded wooded lot. Landscaped grounds in a premier area of Islamorada, Florida known as "Millionaires Row" Enjoy spectacular Sunrises, on a private Sandy Beach with Ocean Breeze and a private heated saltwater pool with hot tub. Dock for boat and fishing. First level offers one bedroom with king size bed, with ocean views....
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:4
Sleeps:8
Bathrooms:3
Rating Overall Score100%
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Excellent
Anglers Reef Ocean View Boat dock available
2br Boat
2 Bedrooms
2 Bathrooms
6 Sleeps
Parking,
Wifi
- Details
Description
Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -is one of the best kept secrets in the Keys. Outstanding ocean views from your back porch, living room and upstairs master bedroom private patio. View my other Anglers Reef Property: vrbo 677953 and 491200 Florida State Licensed Single Family Dwelling No. DWE5403660. City of Islamorada Vacation Rental License No. VR-216 Upstairs master...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:2
Rating Overall Score100%

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Vacation Rentals in Islamorada

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Homeaway and more. AllTheRooms has 1177 vacation rentals, hotels and other great places to stay during your time in Islamorada, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. The average price of accommodation in is $851 per night.

Those looking to get some work done during their trip to Islamorada can pick from 221 places to stay that provide WiFi. 16 places to stay include a breakfast. Choose from 16 places to stay that provide gym facilities, so you won't miss a single workout. Driving to Islamorada? Then choose one of the 217 places to stay that comes with a parking spot included. 150 hotels and vacation rentals have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 71 accommodations that are designated as pet-friendly.

In Islamorada AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 212 places to stay from Airbnb, 129 accommodations from VRBO and 129 places to stay from Homeaway.

455 accommodations in Islamorada have been reviewed: 37% are rated excellent or good. 259 accommodations allow instant booking.

The Best Islamorada Vacation Rentals (Florida) in September 2018

Vacation Rentals in Islamorada

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Rentals in Islamorada