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Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world...
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Savor a sun-filled vacation in this charming oceanfront condo, complete with sweeping ocean views and shared amenities such as a gym, saunas, a pool, tennis courts, laundry facilities, barbecues, and a party room.
In the Sea Gull Condos complex, this rental is less than one mile off Old Highway 1...
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2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6
This magnificent 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...
My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP.
***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY***
Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!...
Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit. Â There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the...
Welcome to your beach-front oasis on the bay side at mile marker 74 in Islamorada, the Sport Fishing Capital of the World. Dig your toes in the sand, bask in the warm, clean waters and soak up the sun at this beautiful retreat. For the fishermen and divers there is a shared dock and boat ramp on...
Loved the home. Everything that was advertised was available and easy to use and find. Nice pool, access to the beach, and close to tons of activities. We were here for a family...
I highly recommend this vacation rental! Very clean the pictures online are exactly what you see when you enter this beautiful home. It’s safe, convenient, well decorated...
*** Owner is highly motivated to rent! Contact us for discounts ***
Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
*** Owner is highly motivated to rent! Contact us for discounts ***
Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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About this property
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...
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Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76.
Near the...
This relaxing private home, known as "Windley Cottage" is located in Angler's Reef, Islamorada's premier gated oceanfront community with private beaches, boat docks (available for rent), and a resort-style swimming pool overlooking the boat dock lagoon, beaches, and the Atlantic ocean....
"The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either.
Located on a narrow residential peninsula in Lower Matecumbe Key, the...
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
This house was absolutely great! I loved that it had a dock and I was able to bring my boat with me instead of having to leave it at a marina. I stayed here for a week with a...
*** Owner is highly motivated to rent! Contact us for discounts ***
This water front home is located oceanside in the tropical Lower Matecumbe key, Islamorada, mile marker 73 (The Sport Fishing Capital of the World). It features a 15' wood dock and 12’ wide ramp, so you can bring your own boat and...
This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014!
Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in the...
We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the...
This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in
Lower Matecumbe (South part of Islamorada). This home is the second one in on a point
and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee
maker, toaster, and blender. There are two...
Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
Your awe moment begins as you drive through the gates of the Moja Draga Estate, located on a beautiful 2 acre parcel of prime ocean front property in the village of Islamorada. Moja Draga is where your vacation dreams begin. Your island vacation home is well appointed with all that you need for a...
Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included.
Near the house is the small Anne's Beach. There are nature trails, board walks to...
We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
Amazing ocean views can be enjoyed from this beautiful stilt home with separate mother- in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile...
Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key.
Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800 per...
What else can be said about this property? It has everything. Pool – check, beach – check, ocean view – check, a gym, and even your own personal luxury outdoor shower. My...
***** Amazing Home For An Amazing Price Through January 31st, 2017
Live your tropical dream at this palatial oceanfront estate that is newly available through Freewheeler Vacations. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about...
This townhome at Executive Bay will sure make your home away from home! Â This unit has been completely renovated and decorated beautifully. Â This
2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
Keys home in Anglers Reef with ocean view, dock, community pool & private beach
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...
Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100" Â concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,...
The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
On our recent family trip to the keys, we were lucky enough to find this amazing home. We stayed for one week and wish we had stayed a month!The house is 6 stars and the hosts...
***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
Beautiful 4 bedroom 4.5 bath home located in Venetian Shores. Â The home has a great kitchen that opens up to the living room. Â You can even play a game of pool in the room off the living room. Â Upstairs there is a master suite that has a great porch that you can sit and enjoy your morning coffee...
Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs. Â The downstairs apartment has a complete kitchen and living room and separate bedroom. Â There is a screened in porch of the living room upstairs. Â The home has awesome...
Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing views of the Clear Blue...
Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo, on mile marker 74).
Welcome to our little slice of paradise in the Florida Keys!
Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit...
Great place to setup home base in the Keys. The home had everything we needed, including a fully stocked kitchen for cooking our fresh catch. Nice, quiet community with many...
House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5)
Islamorada home set in OceanFront gated community with swimming pool and private boat dock
This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
Alligator Reef is the Perfect getaway for large groups! You can rent from 1 to 4 homes depending on the size of your group.
The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool. The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people. (Sofa...
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6
This beautiful 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...
Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
Minimum Rental: 28 Days "Lyons Landing" is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and...
Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people.
The Upper Duplex & The...
We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys.
It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Offering Modern Granite Counter Tops and Stainless Steel Appliances. Plush...
This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the...
Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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About this property
Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a...
This magnificent home with 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. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers Reef is a quiet oceanfront...
Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost...
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
Beautiful home with great access to boat launch and dockage at the house. Very neat and clean and every amenity you could want. Had some AC problems that Keys Holiday Rentals...
Minimum Rental: 28 Days "Casa Dorado" is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal...
License #: VR-215, DWE5403682
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...
Beautiful 2 bedroom 2 bath, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and this unit has ocean views. Some...
Minimum Rental: 28 Days "West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter...
Minimum Rental: 28 Days "Manatee Manor" is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier Creek...
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