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Explore Islamorada from Your Luxury Lodging

Luxury rental homes are available in Islamorada, Florida, with up to five bedrooms that will accommodate a dozen people in comfort and style. Many of these residences are oceanfront, and you can even find one that includes your own private fishing pier and swimming pool. Linens are provided, and each dwelling includes a washer and dryer. The homes are beautifully furnished and come with completely outfitted kitchens.

Eco-tours

Tour companies in Islamorada offer a variety of walking and boating tours. An eco-tour will give you a chance to see the gorgeous natural scenery of the Florida Keys up close. The Indian Key walking tour combines land and sea, with a twenty-minute kayak ride to the beautiful and unspoiled island of Indian Key. The tour includes a narrated description of the rich history of this unique island.

Water Sports

There are a lot of options when it comes to water sports in Islamorada. Jets ski and boat rentals are available, and there are plenty of guided boat tours. Fishing, diving and snorkeling gear can be rented, along with transportation to locations like Alligator Reef, a marine sanctuary filled with sea life. Reservations are recommended to make sure that the equipment you need will be available.

Sport Fishing

Islamorada has the largest sport fishing fleet in the Florida Keys. Fishing tournaments are held there every year, with bonefish and sailfish being the main objects of pursuit. Fishing excursions are offered for visitors, and some restaurants will even cook your catch for a small fee.

Dining and Nightlife

Local Restaurants

No matter what kind of food you prefer, you can find it at one of the many popular restaurants on Islamorada. Naturally, seafood is the specialty, but restaurants like the M.E.A.T. Eatery and Taproom also offer delicious burgers and steaks along with pulled pork. Chef Michael's offers upscale dining for lunch or dinner, and their ceviche is one of the house specialties. The menu also offers delicious crab soup and lobster tempura.

Local Music Scene

The nightlife on Islamorada is low-key and laid-back, with a tropical vibe. Florida Keys Brewing Company and Islamorada Fishing Club are two of the popular spots for kicking back with a craft brew or a frozen drink. Lazy Days Restaurant and Sharkey's Pub and Galley offer live, local music in the evening.

Weather

Islamorada is sunny and warm just about year-round. Temperatures in the winter range from the mid-sixties to the high seventies, and the thermometer rarely tops ninety degrees in the summer. Spring and fall are the best times to visit because it's warm enough to lie on the beach but not too hot to enjoy outdoor activities. From the beginning of October to the end of May, there are very few rainy days.

How to Get There

To reach Islamorada by plane, it's best to fly into the Miami or Ft. Lauderdale airport. Once you arrive, there are several car and van rental companies to choose from. Shuttles also operate from the airport to Islamorada and other locations in the Florida Keys. Some of them provide luxuries like mini-bars, and all of them are air-conditioned.

If you are driving, take Exit 4 from the Florida Turnpike. This will connect you to Route U.S. 1, a highway that extends all the way through the Keys. But be careful, because speed limits are enforced in the area. Greyhound Bus also provides a shuttle to the Keys, and this is a picturesque way to see the sights along the way.

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Viewed 170 times in the last 48 hours
  • 1 BR
  • 1 BA
$95
avg/night
House #1055960vb
Viewed 248 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1400 sq. ft.
avg/night
Townhome #1090112vb
2
Viewed 204 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1040 sq. ft.
avg/night
House #1156382vb
2
Viewed 34 times in the last 48 hours
  • 2 BR
  • 2 BA
avg/night
Townhome #1030281vb
3
Viewed 58 times in the last 48 hours
  • Studio
  • 1 BA
  • 400 sq. ft.
Wonderful! 4.9/5
(27 reviews)
$72
avg/night
Studio #866430vb
27
Viewed 83 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1 HF BA
  • 1387 sq. ft.
avg/night
House #4298356
Viewed 142 times in the last 48 hours
  • 2 BR
  • 2 BA
Wonderful! 4.9/5
(20 reviews)
avg/night
House #133481vb
20
Viewed 19 times in the last 48 hours
  • 1 BR
  • 1 BA
  • 575 sq. ft.
avg/night
Condo #971245vb
Viewed 26 times in the last 48 hours
  • 2 BR
  • 3 BA
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Townhome #1139578vb
1
Viewed 27 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1400 sq. ft.
avg/night
Townhome #1107240vb
1
Viewed 33 times in the last 48 hours
  • 2 BR
  • 2 BA
Excellent! 4.3/5
(9 reviews)
avg/night
Townhome #380165vb
9
Viewed 52 times in the last 48 hours
  • 3 BR
  • 3 BA
avg/night
House #1211334vb
Viewed 33 times in the last 48 hours
  • 1 BR
  • 1 BA
Good! 3.7/5
(6 reviews)
avg/night
Condo #690152vb
6
Viewed 54 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1 HF BA
Wonderful! 4.8/5
(41 reviews)
avg/night
House #3970025
41
Viewed 33 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1 HF BA
  • 1376 sq. ft.
Wonderful! 4.9/5
(32 reviews)
avg/night
House #507954vb
32
Viewed 96 times in the last 48 hours
  • 3 BR
  • 2 BA
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Condo #1212803vb
Viewed 18 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1470 sq. ft.
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House #4555954
Viewed 46 times in the last 48 hours
  • 3 BR
  • 2 BA
Wonderful! 4.8/5
(10 reviews)
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Condo #324205vb
10
Viewed 13 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • 1500 sq. ft.
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House #4546416
Viewed 84 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1300 sq. ft.
Excellent! 4.5/5
(15 reviews)
avg/night
House #686520vb
15
Viewed 48 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1 HF BA
  • 1522 sq. ft.
Exceptional! 5/5
(19 reviews)
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House #677953vb
19
Viewed 137 times in the last 48 hours
  • 3 BR
  • 3 BA
Wonderful! 4.9/5
(17 reviews)
avg/night
House #24330vb
17
Viewed 35 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1172 sq. ft.
Wonderful! 4.9/5
(17 reviews)
avg/night
Condo #863892vb
17
Viewed 7 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1 HF BA
  • 1644 sq. ft.
View details for price
Townhome #4473415
Viewed 44 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1152 sq. ft.
Very Good! 4/5
(7 reviews)
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Condo #884970vb
7
Viewed 18 times in the last 48 hours
  • 1 BR
  • 1 BA
avg/night
House #4555907
Viewed 69 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 525 sq. ft.
avg/night
House #1186950vb
Viewed 22 times in the last 48 hours
  • Studio
  • 1 BA
  • 1200 sq. ft.
avg/night
Cottage #843959vb
1
Viewed 86 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 525 sq. ft.
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House #1241858vb
Viewed 45 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1594 sq. ft.
avg/night
House #4555893
1
Viewed 41 times in the last 48 hours
  • 1 BR
  • 1 BA
  • 1 HF BA
  • 968 sq. ft.
Exceptional! 5/5
(8 reviews)
$83
avg/night
Condo #724831vb
8
Viewed 64 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1179 sq. ft.
Excellent! 4.5/5
(35 reviews)
avg/night
Condo #454283vb
35
Viewed 30 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1300 sq. ft.
avg/night
House #911239vb
3
Viewed 49 times in the last 48 hours
  • 1 BR
  • 800 sq. ft.
avg/night
Guest House #4729283
2
Viewed 74 times in the last 48 hours
  • 2 BR
  • 2 BA
Wonderful! 4.9/5
(17 reviews)
avg/night
Condo #795441vb
17
Viewed 25 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 853 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
Condo #788846vb
7
  • 1 BR
  • 1 BA
View details for price
Mobile Home #4818207
Viewed 28 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 980 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
Condo #748932vb
6
Viewed 96 times in the last 48 hours
  • 1 BR
  • 1 BA
Excellent! 4.4/5
(35 reviews)
avg/night
Condo #9904vb
35
Viewed 50 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1176 sq. ft.
Wonderful! 4.8/5
(48 reviews)
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Condo #77221vb
48
Viewed 27 times in the last 48 hours
  • 1 BR
  • 1 BA
  • 650 sq. ft.
Excellent! 4.7/5
(35 reviews)
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Condo #197265vb
35
Viewed 49 times in the last 48 hours
  • 2 BR
  • 2 BA
Wonderful! 4.9/5
(14 reviews)
avg/night
Condo #18699vb
14
Viewed 42 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 900 sq. ft.
Excellent! 4.4/5
(9 reviews)
avg/night
Condo #784682vb
9
Viewed 99 times in the last 48 hours
  • 2 BR
  • 2 BA
Exceptional! 5/5
(6 reviews)
avg/night
Condo #1021237vb
6
Viewed 52 times in the last 48 hours
  • 2 BR
  • 2 BA
avg/night
House #4779222
Viewed 16 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1100 sq. ft.
Wonderful! 4.9/5
(7 reviews)
avg/night
Condo #4191272
7
Viewed 19 times in the last 48 hours
  • 1 BR
  • 1 BA
$95
avg/night
Condo #1251151vb
Viewed 69 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1 HF BA
  • 1200 sq. ft.
Exceptional! 5/5
(23 reviews)
avg/night
House #899629vb
23
  • 2 BR
  • 1 BA
avg/night
House #981778vb
Viewed 26 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • 850 sq. ft.
Excellent! 4.7/5
(28 reviews)
avg/night
Condo #17144vb
28

Islamorada: Houses, Condos & More (300+)

 

Recent Islamorada Reviews

Beautifully appointed home with very responsive owners

5 of 5
Our family rented three homes in Anglers Reef and Windley Key surpassed all expectations. The home is child ready which was perfect for our son and his young children. The owners obviously love their home and that shone through on all of our conversations with them from the initial to closing contacts. We would highly recommend this home.
  • Submitted: Jan 09, 2018
  • Stayed: Dec 2017

Nice and quiet

4 of 5
Property was cute with lovely ocean views. Very quiet there. Everything is 10-15 minutes from the property. Groceries are 15-20 + drive. Place was nice for a lazy sort of vacation. We enjoyed renting kayaks and paddle boards for daytime fun. The yard is small and after Irma, there is no "beach" as it once had, but we dealt with it. Lots of Iguanas on the property which were fun to watch from the balcony.We would return for a laid back vacation.
  • Submitted: Nov 08, 2017
  • Stayed: Oct 2017