Islamorada Waterfront Vacation Rentals, Homes, & More - 58 Rentals Available

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1 / 24

Islamorada Home
5 BR / 5 BA / Sleeps 15 5 15 7 night min stay
Home / 5 Bedrooms / Sleeps 15
5 bedrooms 5 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
"This is the second time we've rented this house and it was better than the first time. Beautiful views and easy access to the bay was exactly what we were looking for. The new ice maker and huge refrigerator were perfect for our large group. Amazing unobstructed..."
- Brian Barnes, Denver, CO
(9) Excellent (9 reviews)
1 / 9

Islamorada Home
4 BR / 4 BA / Sleeps 8 4 8 full period
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Microwave • Air Conditioning
"We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better, we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish, we caught ..."
- Lynne Kersey Coffey, Deland Florida
(7) Excellent (7 reviews)
1 / 29

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Not more I can say except we all had a great time and thanks to the hosts and location this was an amazing celebration! Definately recommend!"
- Andrew Dick, Tacoma, WA
(10) Excellent (10 reviews)
1 / 22

Islamorada Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"My husband and I had the pleasure of staying at this beautiful condo. The views were amazing. We used the pool daily and was a great place to relax. The owners made sure every last detail was taken care of. Love this condo!"
- Anne Sullivan, Chicago
(1) Excellent (1 review)
1 / 15

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 30 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property."
- Key Rosser, Bradenton,Fl
(9) Excellent (9 reviews)
1 / 9

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 4 2 4 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Microwave • Air Conditioning
"What a great place to stay Perfect for boating, fishing or just relaxing - cant wait to go back!"
- Rob Apostolakis, Chicago, IL
(6) Excellent (6 reviews)
1 / 6

Islamorada Home
2 BR / 1 BA / Sleeps 5 2 5 30 night min stay
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
"Thank you Robert and Joan for the use of your rental home in Islamorada! My husband and two daughters had an enjoyable week long vacation staying here. There is plenty of space, comfort, and amenities! The couple staying downstairs were also very ..."
- Tiffany Davis, Haverford, PA
(4) Excellent (4 reviews)
1 / 29

Islamorada Home
3 BR / 3 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This house is the best! ! ! ! ! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own..."
- Shannon Smiles, Wilmington, NC
(21) Excellent (21 reviews)
1 / 17

Islamorada Home
4 BR / 3 BA / Sleeps 12 4 12 30 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"We have stayed at this home 2 years in a row and have enjoyed ourselves tremendously! It has a great location at the end of the street, corner lot, pool privacy, and water front. The house is large enough to accomodate our large family and give privacy..."
- julie forbush, Michigan
(18) Excellent (18 reviews)
1 / 6

Islamorada Townhouse
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The location is perfect! It is very orivate with an amazing view. The condo is in pristine condition! We will definitely come again!"
- Caroline McCurry, South Carolina
(7) Excellent (7 reviews)
1 / 28

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We enjoy coming back, weather just great. Just so relaxing. Chiki bar, pool, private dock all a plus. Est place to vacation."
- Joan Geissler, Lake Worth, Florida USA
(3) Excellent (3 reviews)
1 / 12

Islamorada Condo
2 BR / 2 BA / Sleeps 5 2 5 Min stay varies
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
Dishwasher • Microwave • Air Conditioning
"Condo is quiet and private, large balcony and view was spectacular. Clean and well stocked. Plenty of room for 5. Owner easily available by text or email, Would highly recc for others"
- bev nelson, gainesville, florida
(21) Excellent (21 reviews)
1 / 9

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"What a lovely place. Immaculately clean and beautifully appointed. Everything as advertised and the pool and hot tub are beautiful. Nicely situated in Lower Metacumbe. The private beach was a gorgeous addition.We had a wonderful time and Capt. Mark..."
- Bryan Loveless, Columbus, Ohio
(7) Excellent (7 reviews)
1 / 16

Islamorada Condo
2 BR / 2.5 BA / Sleeps 4 2 4 No min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The house was so nice, everything you could possible need. The view from the lanai is superb, Bobbie was a great owner, would answer your call for anything. The complex is quiet, and the people are friendly. What an amazing vacation! !"
- Denise McDade, central coast california
(1) Excellent (1 review)
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