Vacation Rentals in Islamorada - HomeToGo base64Hash Vacation Rentals in Islamorada - HomeToGo

Vacation Rentals in Islamorada

Find 1,856 available offers from 7 partners
Islamorada
Anytime
Guests
Ukraine Crisis Relief - Find and Offer Accommodation. Learn more

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Condo
Apartment
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Enjoy an idylic beach vacation at your Islamorada vacation home

Islamorada was where back country sport fishing and salt water fly fishing first burst onto the scene. The 'fishing capital of the world' also has the world's highest density of professional offshore charter boats. Islamorada, which means "purple isles," is also a popular wedding destination, thanks to its raw beauty and crystal blue waters. There's much happening here, from exciting fishing activities to art walks and romantic seaside cafés. Book your Islamorada vacation rental to see what's in store.

Show all 1,856 properties
Save up to 31%

Best Vacation Home Deals in Islamorada

House Islamorada
Apr 17 - Apr 24
-22%
$452
$351 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Islamorada with Private Parking
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Aug 19 - Aug 26
-20%
$339
$271 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Islamorada with Pool & Grill
4.9
"Excellent" (45 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Oct 8 - Oct 15
-31%
$550
$378 per night
House ∙ 5 guests ∙ 2 bedrooms
Family Friendly Charming House in Islamorada with Great Pool
5.0
"Excellent" (87 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal

Discover a vacation home meeting your expectations among the 1,856 welcoming options from 7 providers in Islamorada. Using HomeToGo you can instantly search and compare the prices of each available property to discover the best deal and save up to 53%.

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Islamorada

Condo Islamorada
Aug 19 - Aug 26
-33%
$299
$200 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Islamorada with Clean Pool + Ocean Views
4.9
"Excellent" (140 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Jan 16 - Jan 23
-50%
$3,200
$1,600 per night
House ∙ 4 guests ∙ 7 bedrooms
Vacation Home in Islamorada with Grill & Pool + Close to Beach
5.0
"Excellent" (53 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Sep 16 - Sep 23
-23%
$356
$274 per night
House ∙ 4 guests ∙ 2 bedrooms
Pleasant Vacation Home in Islamorada with Outside Patio
5.0
"Excellent" (1 rating)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $130 per night

Villa Islamorada
Jun 26 - Jul 3
$229 per night
Villa ∙ 4 guests ∙ 1 bedroom
Villa in Islamorada with Yard & Grill
4.9
"Excellent" (103 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Nov 1 - Nov 8
$158 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Entire Condo in Islamorada with Pool, Grill & Yard
5.0
"Excellent" (49 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Apr 14 - Apr 21
$211 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Pool & Grill
5.0
"Excellent" (11 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Apr 29 - May 6
$130 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Sauna, Pool & Grill + Ocean View
4.9
"Excellent" (84 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Apr 22 - Apr 29
$500 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Islamorada with Grill, Yard & Pool + Nice Views
5.0
"Excellent" (59 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Cottage Islamorada
Oct 8 - Oct 15
$270 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Lovely Cottage in Islamorada with Grill & Yard + Next to Beach
5.0
"Excellent" (71 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
May 27 - Jun 3
$775 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Islamorada with Yard, Grill & Pool
4.8
"Excellent" (70 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Cottage Islamorada
Oct 8 - Oct 15
$225 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Islamorada with Grill + Ocean Views
5.0
"Excellent" (111 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Sep 30 - Oct 7
-24%
$1,307
$995 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Islamorada with Yard, Grill & Pool + Ocean Views
5.0
"Excellent" (61 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
See all offers
Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Islamorada

Condo Islamorada
Sep 23 - Sep 30
-23%
$165
$127 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Private Balcony
4.5
"Outstanding" (93 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Oct 14 - Oct 21
$175 per night
House ∙ 6 guests ∙ 2 bedrooms
Nice House in Islamorada with Olympic-Sized Pool
4.9
"Excellent" (17 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Sep 23 - Sep 30
-27%
$220
$160 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Grill
5.0
"Excellent" (2 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal

Vacation rentals and apartments with air conditioning

Keep cool during your trip to Islamorada and book a vacation rental with air conditioning.

Condo Aircondition Islamorada
May 20 - May 27
$130 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Sauna, Pool & Grill + Ocean View
4.9
"Excellent" (84 ratings)
Islamorada, Monroe County, Florida, United States
Aircondition
Details
Vrbo
View deal
View deal
Boat Aircondition Islamorada
Aug 25 - Sep 1
$365 per night
Boat ∙ 4 guests ∙ 2 bedrooms
Charming Boat in Islamorada with Yard & Grill
4.9
"Excellent" (185 ratings)
Islamorada, Monroe County, Florida, United States
Aircondition
Details
Vrbo
View deal
View deal
House Aircondition Islamorada
Apr 29 - May 6
$210 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Pool & Grill
5.0
"Excellent" (11 ratings)
Islamorada, Monroe County, Florida, United States
Aircondition
Details
Vrbo
View deal
View deal
See all offers

Vacation rentals with Wi-Fi

Stay connected while traveling and book a Islamorada accommodation with high-speed internet.

House Internet Islamorada
May 13 - May 20
$175 per night
House ∙ 6 guests ∙ 2 bedrooms
Nice House in Islamorada with Olympic-Sized Pool
4.9
"Excellent" (17 ratings)
Islamorada, Monroe County, Florida, United States
Internet
Details
Vrbo
View deal
View deal
Condo Internet Islamorada
Sep 3 - Sep 10
-36%
$399
$258 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Nice Condo in Islamorada with Yard, Pool & Grill + Ocean View
5.0
"Excellent" (133 ratings)
Islamorada, Monroe County, Florida, United States
Internet
Details
Vrbo
View deal
View deal
Cottage Internet Islamorada
Sep 2 - Sep 9
$225 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Islamorada with Grill + Ocean Views
5.0
"Excellent" (111 ratings)
Islamorada, Monroe County, Florida, United States
Internet
Details
Vrbo
View deal
View deal
See all offers

Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Islamorada rental with full kitchen.

House Kitchen Islamorada
Aug 25 - Sep 1
-19%
$356
$287 per night
House ∙ 4 guests ∙ 2 bedrooms
Pleasant Vacation Home in Islamorada with Outside Patio
5.0
"Excellent" (1 rating)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Vrbo
View deal
View deal
House Kitchen Islamorada
Aug 25 - Sep 1
-22%
$449
$350 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Islamorada with Private Parking
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Vrbo
View deal
View deal
Condo Kitchen Islamorada
Jul 22 - Jul 29
-43%
$359
$205 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Pool
4.8
"Excellent" (175 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities in Islamorada

  • Internet (1,793)
  • TV (1,702)
  • Air conditioning (1,585)
  • Microwave (1,530)
  • Pool (1,472)
  • Kitchen (1,396)
  • No smoking (1,359)
  • No pets (1,138)
  • Fishing (1,099)
  • Grill (1,072)
  • Washer (937)
  • Dishwasher (934)

Check above for the most selected filters in Islamorada and the number of vacation rentals that offer them. Many properties in Islamorada offer "Internet" or "TV," which makes it a wonderful vacation destination if you need internet access during your vacation or you want to tune out with some TV time. You could even look for rentals if you enjoy soaking in the hot tub (41 rentals include "Hot tub" in Islamorada) or if you want a rental with a sauna (31 rentals in Islamorada include "Sauna").

The Weather in Islamorada

max.
Min.
81°
70°
7 days 7
max.
Min.
79°
68°
6 days 6
max.
Min.
81°
70°
7 days 7
max.
Min.
86°
75°
6 days 6
max.
Min.
88°
77°
9 days 9
max.
Min.
90°
79°
12 days 12
max.
Min.
91°
81°
13 days 13
max.
Min.
91°
81°
14 days 14
max.
Min.
90°
79°
16 days 16
max.
Min.
86°
75°
11 days 11
max.
Min.
81°
72°
9 days 9
max.
Min.
79°
70°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Islamorada climate diagram. On average, the warmest month is July. On the contrary, the coolest month is February. The rainiest month is September while the driest month is February.

7-Day Weather Forecast in Islamorada

Thu, 2 Feb
77°
75°

15%

2 h

13 mi/h

Fri, 3 Feb
77°
75°

15%

4 h

9 mi/h

Sat, 4 Feb
75°
71°

15%

6 h

15 mi/h

Sun, 5 Feb
77°
75°

15%

7 h

7 mi/h

Mon, 6 Feb
75°
71°

15%

10 h

8 mi/h

Tue, 7 Feb
75°
75°

15%

5 h

17 mi/h

Wed, 8 Feb
77°
75°

15%

8 h

14 mi/h

Accommodations for your vacation in Islamorada

In Islamorada, many of the 1,856 vacation properties are house rental, which represent 69.54% of its listed properties. Additionally, the average nightly price of house rental there is $832, and the median size is 156 m². Furthermore, these accommodations are perfect for large groups, as most can accommodate 7 guests. If you would prefer to compare another accommodation type, you may want to check apartment rental, which are the second most frequent accommodation type in Islamorada. The average size of apartment rental in Islamorada is 116 m², and the average price is $504 per night.
Where to find the best food in Islamorada?

Cuisine of Islamorada

Seafood enthusiasts won't be disappointed with Islamorada's culinary offerings. Choose from fresh-off-the-nets seafood served in all kinds of settings — tiki-covered huts, marina-facing fish houses, beachfront cafés or romantic, secluded bistros. The waterfront is dotted with restaurants, serving everything from Mediterranean cuisine, sushi, organic salads, sandwiches and meatball subs.

Enjoy dinner and live entertainment at the waterfront cafés that serve excellent seafood: there's fried oysters, peel-and-eat-shrimp, and fish sandwiches galore. For the "freshest sushi in all the Keys!" and a hefty beer, wine and sake list, Kaiyo Grill & Sushi does the trick. Don't forget to pack some takeaway to feast on when you return to your Islamorada vacation rental.

What is the weather like in Islamorada?

The weather in Islamorada

The best time to visit is between December and May, when outdoor activities can be enjoyed under sunny, blue skies. Your vacation home in Islamorada should be booked in advance during this peak season. For those who prefer some peace and quiet, as well as discounted prices on rentals, October and November is a great time to visit.

What are the top sights in Islamorada?

The must-see sights of Islamorada

Most people come to Islamorada for its scenery and sunsets. The sea facing restaurants are perfectly aligned to allow diners gorgeous views of the sun sinking into the ocean. From the Islamorada Fist Company restaurant, you can watch sharks being fed while you enjoy your evening meal, as the event usually takes place around sunset. It's also quite possible to enjoy the sunset from the privacy of your sea-facing vacation rental on Islamorada.

Enjoy tropical evenings with relaxed music at the waterfront ICE Amphitheater, housed inside Islamorada Founders Park. This pet-friendly park also features an Olympic-sized pool, ball fields, a shallow water beach, water sports rentals and a skate park. Casa Mar Village meanwhile, is recommended for its local fish market, waterfront shopping and outdoor adventure sports activities. The kids will enjoy hand-feeding giant silver tarpons at Robbie's Marina. Then take them to a fun dolphin, sea lion and parrot show at Theater of the Sea marine mammal park.

What are the best places to discover the arts and culture of Islamorada?

Art and culture on Islamorada

The Coral Shores Performing Arts Center delights audiences with its top-notch productions. Meanwhile the monthly Third Thursday Art Walk organized by the Morada Way Arts & Cultural District is a great way to get acquainted with the town's art spaces and boutiques. The event brings together artisans, sculptors, jewelers, photographers and travelers who enjoy the artist receptions, music, sunsets and other fun activities.

The Jannette De Llanos Art Gallery showcases oil paintings and graphic art of the Florida Keys & beyond, while the Pasta Pantaleo Signature Gallery houses Pasta's sportfish paintings that are vivid and rich in their color schemes. For a look at the artworks of local photographers, painters, sculptors, and mixed media artists, visit Gallery at Ocean Sotheby's International Realty. Lastly, there's Crane Point Museum & Nature Center which regales visitors with its interpretative displays of marine life, local wildlife and exhibits.

Where are the unique attractions in Islamorada?

Excursions and day trips beyond Islamorada

Islamorada boasts rare and extraordinary brimming patch reefs, which is good news for divers. An hour south from your vacation home on Islamorada, lies the Bahia Honda State Park where oceanside camping is possible. Enjoy kayaking, fishing, biking, and snorkeling among other great activities. Take time off to explore Islamorada's colorful shallow coral reefs, its shipwrecks, and an interesting underwater hub for scientific research, called the Aquarius.

Pickles Reef is perfect to spot flamingo tongue cowries and banded coral shrimps. Bud n' Mary's is another popular marina known for its sportfishing shows, chartered fishing expeditions, pontoon boats, and deli's serving excellent coffee by the sea. End the day by retiring back at your sea facing Islamorada vacation rental.

Legendary authors such as Ernest Hemingway have been inspired right here in Islamorada! Come over with the family and book your vacation rental on Islamorada today. The isles are waiting.

What are the must-see attractions in Islamorada?

Incredible Islamorada

Lobster Trap Art Gallery

The vivid artworks at this exciting gallery will ensnare your gaze just like the lobsters in the traps outside its doors.

The Rain Barrel Artisan Village

The perfect day out involves exploring this picturesque artists' village, where there are any number of craft workshops to get involved in, plus exquisite art to discover and take home. Jewellery, sculpture and fine art are just the start.

Florida Keys Brewing Company

This family run microbrewery is a delight, and is ideally situated in the arts and cultural district of town. Enjoy tours, talks and of course, tastings.

History of Diving Museum

A trip to Florida isn't complete without exploring the ocean. Learn about the technical and historical aspects of this pastime through oral exhibits and artefacts found beneath the waves.

Theater of the Sea

Live the dream and swim with Flipper at this incredible center, dedicated to marine life. Seals, dolphins and parrots perform in mesmerising sealife shows.

Frequently Asked Questions

How many vacation rentals are available to book in Islamorada?

September has the highest amount of available House rental and Apartment rental in Islamorada, so you can expect plenty of offers, even for last-minute bookings.

What amenities are most popular for vacation rentals in Islamorada?

Travelers search for TV, Internet, and Pool when booking a vacation rental in Islamorada.

Are pets allowed in vacation homes in Islamorada?

Finding a vacation rental in Islamorada that allows pets is easy, with 345 pet-friendly available.

What's the best time of year to travel to Islamorada?

July and August are usually the warmest months in Islamorada with temperatures around 91 °F. The coldest months in Islamorada are February and January, with 68 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Islamorada TripAdvisor Vacation Rentals in Islamorada Vrbo Vacation Rentals in Islamorada VacationRentals.com Vacation Rentals in Islamorada HouseTrip Vacation Rentals in Islamorada FlipKey Vacation Rentals in Islamorada Homestay.com Vacation Rentals in Islamorada Only-apartments Vacation Rentals in Islamorada Interhome Vacation Rentals in Islamorada Novasol Vacation Rentals in Islamorada HomeEscape Vacation Rentals in Islamorada

Vacation Destinations Near Islamorada

Top Vacation Ideas

Explore More Vacation Ideas

image-tag