Islamorada Vacation Rentals - HomeToGo base64Hash Islamorada Vacation Rentals - HomeToGo

Islamorada Vacation Rentals

Find 1,924 available offers from 7 partners
Islamorada
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Pension
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 1,933 properties
Save up to 25%

Best Vacation Home Deals Islamorada

House Islamorada
Sep. 16 - Sep. 23
-25%
$463
$346 per night
House ∙ 5 guests ∙ 2 bedrooms
Family Friendly House in Key Largo with Pool & Grill
4.7
"Outstanding" (163 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal

Discover a vacation rental that matches your criteria among the 1,924 fantastic vacation rentals from different vacation rental websites in Islamorada. Using HomeToGo's search feature you can immediately search and compare the prices of each available rental to discover the best deal and save up to 45%.

Book Vacation Rentals with the Highest User Rating

Top-Rated Offers and Accommodations Islamorada

Condo Islamorada
May 27 - Jun. 3
$568 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Large Pool + Ocean View
5.0
"Excellent" (55 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Jun. 24 - Jul. 1
$317 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Entire Condo in Islamorada with Pool, Grill & Yard
5.0
"Excellent" (52 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Nov. 19 - Nov. 26
$335 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Pool & Grill + Sunset View
4.6
"Outstanding" (29 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals Islamorada

Find your perfect vacation rental Islamorada: from $221 per night

Cottage Islamorada
Nov. 19 - Nov. 26
$413 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Islamorada with Grill + Ocean Views
5.0
"Excellent" (115 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Nov. 19 - Nov. 26
$349 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Islamorada with Spacious Pool
5.0
"Excellent" (42 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Jul. 15 - Jul. 22
$524 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Family Friendly Condo in Key Largo with Open Balcony + Spectacular Views
4.9
"Excellent" (61 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
May 6 - May 13
$323 per night
House ∙ 2 guests ∙ 2 bedrooms
House in Key Largo with Pool & Grill
5.0
"Excellent" (28 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Nov. 19 - Nov. 26
$577 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Key Largo with Yard, Grill & Pool + Ocean View
4.8
"Excellent" (87 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
May 8 - May 15
$498 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Clean Condo in Tavernier with Pool & Grill
4.6
"Outstanding" (74 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Aug. 5 - Aug. 12
$831 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Layton with Grill + Spectacular View
5.0
"Excellent" (84 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Jul. 15 - Jul. 22
$639 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Key Largo with Serene Garden + Dramatic Views
5.0
"Excellent" (110 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
House Islamorada
Nov. 19 - Nov. 26
$785 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Key Largo with Grill, Pool & Yard
4.9
"Excellent" (84 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
See all offers
Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals Islamorada

House Islamorada
May 6 - May 13
-15%
$699
$592 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Islamorada with Pool, Yard & Grill + Degree Views
4.9
"Excellent" (90 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
Jun. 24 - Jul. 1
$945 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Islamorada with Grill, Yard & Pool + Nice Views
5.0
"Excellent" (62 ratings)
Islamorada, Monroe County, Florida, United States
Details
Vrbo
View deal
View deal
Condo Islamorada
May 8 - May 15
$378 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Islamorada with Pool & Yard + Beautiful View
4.8
"Excellent" (38 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 Air conditioning Islamorada
Aug. 19 - Aug. 26
-25%
$516
$388 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Islamorada with Outdoor Pool + Ocean Views
4.8
"Excellent" (144 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
Details
Vrbo
View deal
View deal
Condo Air conditioning Islamorada
Jul. 15 - Jul. 22
$262 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Sauna, Pool & Grill + Ocean View
4.9
"Excellent" (86 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
Details
Vrbo
View deal
View deal
House Air conditioning Islamorada
May 6 - May 13
-37%
$903
$568 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Electric Fireplace + Ocean Views
5.0
"Excellent" (148 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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.

Condo Internet Islamorada
Sep. 16 - Sep. 23
-15%
$318
$270 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Private Balcony
4.5
"Outstanding" (97 ratings)
Islamorada, Monroe County, Florida, United States
Internet
Details
Vrbo
View deal
View deal
Villa Internet Islamorada
Sep. 9 - Sep. 16
$435 per night
Villa ∙ 6 guests ∙ 2 bedrooms
Beautiful Villa in Islamorada with Olympic-Size Pool
5.0
"Excellent" (89 ratings)
Islamorada, Monroe County, Florida, United States
Internet
Details
Vrbo
View deal
View deal
Condo Internet Islamorada
Jul. 29 - Aug. 5
$383 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Pool
4.8
"Excellent" (177 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.

Condo Kitchen Islamorada
Sep. 2 - Sep. 9
$323 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Key Largo with Private Balcony, Queen Daybed
4.8
"Excellent" (123 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Vrbo
View deal
View deal
Cottage Kitchen Islamorada
Nov. 19 - Nov. 26
$414 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Key Largo with Pool & Grill
4.9
"Excellent" (80 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Vrbo
View deal
View deal
Condo Kitchen Islamorada
May 6 - May 13
-21%
$573
$451 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Charming Condo in Tavernier with Grill, Yard & Pool + Ocean Views
4.9
"Excellent" (83 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities Islamorada

  • Internet (1,716)
  • TV (1,675)
  • Air conditioning (1,617)
  • Microwave (1,491)
  • Pool (1,459)
  • Kitchen (1,363)
  • No smoking (1,278)
  • No pets (1,083)
  • Fishing (1,070)
  • Grill (1,037)
  • Dishwasher (906)
  • Washer (879)

Finding a vacation rental with a pool shouldn't be too hard Islamorada. Most of the vacation rentals have one. In addition, more hotel rooms include a pool than hotel rooms. On average, hotel rooms with pools in Islamorada accommodate 6 people and have an average cost of $1,011 per night. Among these offers, 81 of them are situated within 2 kilometres of water.

The Weather Islamorada

max.
Min.
27°
21°
7 days 7
max.
Min.
26°
20°
6 days 6
max.
Min.
27°
21°
7 days 7
max.
Min.
30°
24°
6 days 6
max.
Min.
31°
25°
9 days 9
max.
Min.
32°
26°
12 days 12
max.
Min.
33°
27°
13 days 13
max.
Min.
33°
27°
14 days 14
max.
Min.
32°
26°
16 days 16
max.
Min.
30°
24°
11 days 11
max.
Min.
27°
22°
9 days 9
max.
Min.
26°
21°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. July is the warmest month Islamorada with average maximum temperatures of 33°. Conversely, February is the coolest month Islamorada, with temperatures going under 20° According to the climate diagram, September is the rainiest month of the year Islamorada.

7-Day Weather Forecast Islamorada

Wed., 22 Mar.
23°
22°

10%

10 h

25 km/h

Thu., 23 Mar.
23°
22°

15%

5 h

25 km/h

Fri., 24 Mar.
23°
23°

5%

7 h

18 km/h

Sat., 25 Mar.
24°
23°

15%

4 h

16 km/h

Sun., 26 Mar.
24°
23°

0%

10 h

18 km/h

Mon., 27 Mar.
24°
23°

10%

10 h

21 km/h

Tue., 28 Mar.
24°
23°

0%

6 h

12 km/h

Where to find the best food 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 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 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 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 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.

Information about vacation rentals Islamorada

🏡 Vacation rentals available 1,933 properties
💳 Discounts available up to 27%
🌙 Price per night from $221
⭐ Popular amenities Internet, TV and Air conditioning
🐾 Pet friendly accommodation options 346 properties
🏊 Vacation rentals with pools 1,595 properties

Frequently Asked Questions

What is the typical price of a vacation home Islamorada?

Accommodation prices Islamorada start at $221 per night.

What is the typical availability of House rentals Islamorada?

We found 1,933 vacation homes Islamorada available for your next trip.

What are the most popular vacation home amenities Islamorada?

The most popular amenities for rentals Islamorada include vacation homes with Internet, TV, or Air conditioning.

How many House rentals and Apartment rentals can I find Islamorada?

Islamorada has 1,933 House rentals and Apartment rentals available to book.

Are there pet-friendly vacation rentals Islamorada?

Finding a vacation rental Islamorada that allows dogs is definitely possible, with 346 pet-friendly homes on offfer.

What's the best month to visit Islamorada?

If you're looking for balmy weather, July and August are typically the hottest months Islamorada with temperatures around 33 °C. February and January Islamorada are the coldest, with 20 °C on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals Islamorada TripAdvisor Vacation Rentals Islamorada Vrbo Vacation Rentals Islamorada Novasol Vacation Rentals Islamorada Inter Chalet Vacation Rentals Islamorada Interhome Vacation Rentals Islamorada HouseTrip Vacation Rentals Islamorada Belvilla Vacation Rentals Islamorada Homestay.com Vacation Rentals Islamorada Ski Planet Vacation Rentals Islamorada Only-apartments Vacation Rentals Islamorada James Villa Holidays Vacation Rentals Islamorada

Vacation Destinations Near Islamorada

Top Vacation Ideas

Explore More Vacation Ideas

image-tag