Feedback

VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

Map view

This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Islamorada Area reviews

  • Wonderful Vacation Oasis in the Keys!

    "This is an amazing place! We loved every minute spent at Osprey Bay Villa this past spring. We were 4 couples trying to get away from our bone-chilling Michigan winter and this place fit the bill perfectly. We all agreed it was one of our best vacations ever and we are going to try to come back again as a group or with our individual families. The house, pool and grounds are well maintained, open, and very clean. There was plenty of space in the house, around the pool or on the dock and property for everyone to be together or to have quiet time alone. The kitchen was large, clean and well equipped, the laundry room was neat and a bonus and the bar area with its own ice machine (another ice machine near kitchen) and sinks both inside and outside next to pool along with a nice grill were perfect for our group. We snorkled and fished from the boat dock which was sturdy and accommodating. We brought our own equipment but there was plenty there for renters to use. It was set up great with the fish cleaning table and a hose that we used to give a visiting manatee drinks of water. There were lots of fish and other wildlife to observe without having to leaving our place. We also spent a lot of time in the pool and spa which are also very well maintained and professionally cleaned twice a week. The location could not be better. We were right in the middle of everything we love about the keys. There are great restaurants, bars and stores within walking distance or a short drive, yet once you leave the main road and head down the driveway, you are totally isolated from the traffic and noise. There was also a rental place across road where you can rent boats and other water toys and we have to make sure to mention the little gourmet restaurant next to the property that served awesome breakfasts, lunchs and dinners. Do not forget to pick up one of their desserts to take back to the house. It makes the sunsets even more perfect. Judy is very accomodating and helpful and all of our transactions were handled promptly and professionally. I agree with another reviewer who said this was important because you are writing a large check and you want to feel comfortable that you can trust the person at the other end. Osprey Bay Villa is wonderful. Judy is great and we all agreed this whole package deserves a 5 star + rating."
    Guest: Jill K. Date of Stay: March 2014 Review Submitted: July 18, 2014
    View listing
  • Wonderful and relaxing!

    "The house was just great! We can't say enough about it. The owners were very nice and helpful. Nice community, (and nice for running in the early mornings.) House was beautifully decorated, clean and very spacious for our two families. Upstairs bedrooms and living space were big and comfortable. Downstairs one bedroom a/c had some difficulty getting going, but it is very nice and big also. The kids enjoyed biking and the little beach so much. The dock was very nice, spacious for our 34'boat, everything well maintained and convenient. Back yard with lush tropical landscaping that we really enjoyed! The tiki was great, will be better with the hammocks! It was very hot during our stay, so we brought the fans outside which made it nicer. Really great features for boaters: great canal access within minutes of bay and ocean, power, water, outdoor shower, ice machine and bait/catch fridge. Alligator reef is just 20 minutes away and stunning. The fish cleaning station was really nice, but better to toss stuff in trash I think since fish remnants can settle around mangroves. We were able to anchor off the little beach and chill after long mornings out in the reef, which was just wonderful. I would avoid it on Saturday and Sunday since everyone else goes those days. But Monday through Friday it's just heaven. Great location for day trips to key west, turtle hospital, or an afternoon tarpon feeding at Robbie's. Only downside is distance from nearest grocery store was a little bit far for me, but nothing that a little advanced planning can't fix. And for everything forgotten there's crazy bills around the corner. Really recommend this beautiful home."
    Guest: Tery G. Date of Stay: June 2014 Review Submitted: June 29, 2014
    View listing
  • Fun time in The Keys

    "This condo is exactly what it is advertized. The views from the balcony are fantastic. There's even a little door in the screening that you can open to get photos without the screen. If you can get up for sunrise - do it! We rented bikes and were able to ride on old route 1 and stay safe from traffic. Rode most days 6-10 miles. We drove to Key West one day (about 2 hours) and spent the day. Founders Beach a mile or so down the road and Sombrero Beach on Marathon Key were great beaches. We also went to the beach at Long Key. Sight-seeing and fishing excursions out of Key Largo were close. We rented kayaks one day right in Tavenier and explored the mangrove swamps along Tavenier Creek. Favorite restaurants: Marker 88 (best food), Ma's Fish Camp (best key Lime pie), Old Tavenier, Made2Order, Morada and Jersey Boardwalk Pizza. We ate most breakfasts and lunches in. Ken was very attentive to all my questions and very easy to work with. A wonderful 2 weeks in the sun."
    Guest: Diana Date of Stay: February 2014 Review Submitted: March 20, 2014
    View listing
  • "STRESS RELIEF"

    "I WANT TO THANK TIM AND JACKIE FOR THE BIT OF HEAVEN WE EXPERIENCED IN OUR STAY AT THE COTTAGE, YOU BOTH ARE THE ULTIMATE HOST. THE PROPERTY IS OUTSTANDING, VERY COMFORTABLE, AND CLEAN, AND WELL TAKEN CARE OF. WE HAD A BALL WITH TIM THE EVENING "WE WENT LOOKING FOR MY TARPON", TIM IS A VERY IMPRESSIVE CAPTIN, AND I PLAN TO USE HIS GUIDE SERVICE AGAIN NEXT YEAR, NOT SURE I AM READY FOR HIS SPEAR FISHING BUT THE TARPON AND SHARK TRIPS ARE UNBELIVABLE. THIS WAS THE BEST STAY WE HAVE HAD IN THE KEYS AND FEEL LIKE WE HAVE MADE NEW FRIENDS WITH JACKIE AND TIM"
    Guest: greg Date of Stay: July 2014 Review Submitted: August 1, 2014
    View listing

Islamorada Area Travel Tips

Islamorada House Rentals are the Ultimate Way to Experience the Florida Keys

For lovers of water activities, the Florida Keys can't be beaten as a vacation spot. The Islamorada area in the lower Keys has some of the best sport fishing in the world, as well as snorkeling, scuba diving, boating and parasailing, all in an environment that averages 75-80 degrees year-round.

The best way to experience the Florida Keys are through Islamorada house rentals. Sure, you could stay in a hotel room, but why do that when you could enjoy your morning coffee and breakfast on the front porch of your private beachfront home? And after an exhilarating but tiring day on the water, you can come "home" to grill your catch and relax in peace and comfort. With Islamorada vacation rentals you CAN have it all!

Incredible Beaches

From your Islamorada beach rentals home venture out to explore the plethora of great beaches; the beach at Plantation Yacht Harbor boasts a nice and deep swimming area. There's great snorkeling at Islamorada County Park, where the beach runs along a natural creek. But watch out for the strong currents here, especially if you're traveling with children. For a cozy beach with a boardwalk, go to Anne's Beach on Lower Matecumbe Key. There are plenty more. Just ask any local to point you in the direction of a great beach.

Enjoy a Night on the Town

Many local restaurants will cook your catch; just because you're staying in Islamorada house rentals, it doesn't mean you have to cook. You're on vacation. Use your Islamorada beach rentals property for the convenience it brings to brew a cup of morning coffee or do a load of laundry without searching for a laundromat, then get the best of both worlds by dining out and partaking of the area's rich nightlife.

Sponsored Advertisement