Holiday homes & rentals in Islamorada - HomeToGo base64Hash Holiday homes & rentals in Islamorada - HomeToGo

Holiday homes & rentals in Islamorada

Find 1,827 available offers from 17 partners
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Top 15 Recommended holiday lettings in Islamorada

Find your perfect holiday home, apartment or cottage in Islamorada from just £88 per night!

House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbeque

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada features a kitchen, balcony, and parking, perfect for accommodating up to eight guests.
from £463
per night
Good(14 ratings)
from £463
per night
View deal
House Islamorada
House ∙ 12 guests ∙ 4 bedrooms

Fully equipped pleasant house with jacuzzi, private pool & barbecue | Pet-friendly

Islamorada, Monroe County, Florida, United States
A stunning house rental in Islamorada featuring a private pool, hot tub, and pet-friendly amenities for up to 12 guests.
from £237
per night
Outstanding(19 ratings)
from £237
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, heated pool & barbeque

Islamorada, Monroe County, Florida, United States
This family-friendly house rental in Islamorada features a heated pool, garden, and balcony, accommodating up to six guests.
from £141
per night
Outstanding(8 ratings)
from £141
per night
View deal
House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

House with private pool & barbecue

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada features a private heated pool, a kitchen, and a balcony, accommodating up to eight guests.
from £575
per night
from £575
per night
View deal
House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly holiday home with garden, terrace & private pool | Nature view | Good for workation | Dogs allowed

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada features a private pool, beach access, and a garden, perfect for families and pets alike.
from £589
per night
Outstanding(103 ratings)
from £589
per night
View deal
House Islamorada
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped house with private pool, terrace & barbecue | Pets are welcome

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada features a private heated pool, waterside balcony, and space for 10, perfect for your getaway.
from £441
per night
from £441
per night
View deal
House Islamorada
House ∙ 9 guests ∙ 2 bedrooms

Family-oriented nice holiday home with garden, BBQ & terrace | Nature view

Islamorada, Monroe County, Florida, United States
This waterside house rental in Islamorada features a garden, balcony, and kitchen, perfect for family gatherings of up to 9.
from £133
per night
Excellent(7 ratings)
from £133
per night
View deal
House Islamorada
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with barbecue, private pool & garden

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada offers a private pool, beach access, and a garden, perfect for a family getaway with pets.
from £834
per night
Excellent(132 ratings)
from £834
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with garden, BBQ & heated pool | Good for workation

Islamorada, Monroe County, Florida, United States
This family-friendly house rental in Islamorada features a heated pool, garden, and parking, perfect for a relaxing getaway.
from £143
per night
Excellent(21 ratings)
from £143
per night
View deal
House Islamorada
House ∙ 14 guests ∙ 3 bedrooms

Holiday home with barbeque, garden & pool

Islamorada, Monroe County, Florida, United States
This Islamorada house rental offers a pool, garden, and kitchen, perfect for family gatherings with space for 14 guests and pets.
from £313
per night
Outstanding(3 ratings)
from £313
per night
View deal
House Islamorada
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly big holiday home with garden, terrace & barbecue | Nature view | Pets allowed

Islamorada, Monroe County, Florida, United States
This waterside house in Islamorada offers beach access, a garden, and a balcony, perfect for family gatherings and pets.
from £705
per night
Outstanding(80 ratings)
from £705
per night
View deal
House Islamorada
House ∙ 8 guests ∙ 2 bedrooms

Holiday home with BBQ

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests, featuring a kitchen and parking for a perfect getaway by the sea.
from £137
per night
Outstanding(1 rating)
from £137
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

Beautiful holiday home with heated pool | Pets allowed

Islamorada, Monroe County, Florida, United States
This Islamorada house rental features a heated pool, pet-friendly policy, and space for up to six guests to relax and unwind.
from £195
per night
from £195
per night
View deal
House Islamorada
House ∙ 10 guests ∙ 4 bedrooms

House with private pool, BBQ & jacuzzi | Suitable for remote work

Islamorada, Monroe County, Florida, United States
This Islamorada house rental features a private heated pool, hot tub, and waterside access, accommodating up to 10 guests.
from £312
per night
Outstanding(3 ratings)
from £312
per night
View deal
House Islamorada
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with terrace

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada features a kitchen and balcony, accommodating up to 8 guests for an unforgettable getaway.
from £173
per night
Outstanding(4 ratings)
from £173
per night
View deal

Holiday lettings and apartments with air conditioning

Villa  Islamorada
from £91 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with barbeque, garden & heated pool | Nature view | Suitable for remote work

4.7
Excellent(28 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
View deal
House  Islamorada
from £438 per night
House ∙ 8 guests ∙ 4 bedrooms

House with BBQ, terrace & private pool | Nature view

4.9
Outstanding(30 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
View deal
House  Islamorada
from £418 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with pool

3.0
(2 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
View deal
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Best holiday homes with a patio or terrace

House  Islamorada
from £257 per night
House ∙ 8 guests ∙ 2 bedrooms

Fully equipped charming house with pool & barbeque

Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
from £141 per night
House ∙ 8 guests ∙ 3 bedrooms

House with terrace & BBQ | Nature view

5.0
Outstanding(3 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
from £850 per night
House ∙ 14 guests ∙ 6 bedrooms

Holiday home with garden, jacuzzi & barbeque | Nature view

4.9
Outstanding(89 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
See all offers

Most popular holiday lettings with a fireplace

House  Islamorada
from £363 per night
House ∙ 5 guests ∙ 2 bedrooms

Family-friendly charming house with heated pool, garden & jacuzzi | Nature view | Pet-friendly

5.0
Outstanding(116 ratings)
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
House  Islamorada
from £1,147 per night
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque, private pool & garden | City view | Perfect for remote work

5.0
Outstanding(70 ratings)
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
House  Islamorada
from £197 per night
House ∙ 6 guests ∙ 2 bedrooms

Holiday home with garden, heated pool & barbecue

5.0
Outstanding(3 ratings)
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
See all offers

Budget-friendly Holiday Homes in Islamorada

Find Fantastic yet Cheap Lettings

Condo Islamorada
from £211 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped pleasant flat with barbeque & terrace

5.0
Outstanding(29 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from £325 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with terrace, barbeque & hot tub

3.0
(1 rating)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from £263 per night
House ∙ 8 guests ∙ 2 bedrooms

House with barbeque, private pool & terrace

5.0
Outstanding(82 ratings)
Islamorada, Monroe County, Florida, United States
View deal

Top-Rated Lettings and Properties in Islamorada

Book Holiday Letting Offers with the Highest User Rating

House Islamorada
from £1,337 per night
House ∙ 16 guests ∙ 5 bedrooms

Children-friendly beautiful holiday home with barbecue, garden & terrace | Good for workation

4.8
Outstanding(100 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from £462 per night
House ∙ 12 guests ∙ 5 bedrooms

House with terrace, garden & private pool

5.0
Outstanding(82 ratings)
Islamorada, Monroe County, Florida, United States
View deal
Condo Islamorada
from £166 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with BBQ, jacuzzi & terrace

4.9
Outstanding(64 ratings)
Islamorada, Monroe County, Florida, United States
View deal

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Spend your budget exactly as planned by comparing thousands of providers.

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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Islamorada

  • Pool (1,537)
  • Air conditioning (1,815)
  • WiFi (1,779)
  • Kitchen (1,341)
  • Fishing (1,279)
  • Grill (1,083)
  • Balcony/patio (939)
  • TV (1,700)
  • Washing machine (923)
  • Microwave (1,313)
  • Pet-friendly (756)
  • No smoking (1,786)

Many holidaymakers would like to find a holiday home with a pool. Most of the accommodation options in Islamorada have this feature. Hotel room with pools in Islamorada are a fantastic option for groups of 6 and usually cost around £539 a night. In Islamorada, more than half of the rentals with a pool are situated close to the water.

Price and Availability Index for Islamorada

Click on any bar to see price and availability information

Holiday Letting Price Information in Islamorada

This graph displays average prices of the holiday cottages and holiday apartments located in Islamorada. The most expensive week during the next 12 months is in December (26/12 – 02/01), when nightly prices hit an average of £797. Conversely, the cheapest average prices are in one week of October (17/10 – 24/10).

Rental availability information in Islamorada

Have a look at the graph above to see the availability of rentals in Islamorada. The week with the highest booking rate is in May (01/05 – 08/05). Only 19 of the rentals are still available. Conversely, it is in August (29/08 – 05/09) that the highest percentage of rentals are available.

Enjoy an idylic beach holiday at your Islamorada holiday accommodation

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 holiday accommodation to see what's in store.

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 holiday letting 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 lettings 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 Theatre of the Sea marine mammal park.

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 holiday 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 holiday letting .

Legendary authors such as Ernest Hemingway have been inspired right here in Islamorada! Come over with the family and book your holiday letting 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.

Theatre of the Sea

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

Information about holiday rentals in Islamorada

🏡 Holiday homes available 1,827 rentals
🌙 Nightly prices from £88
⭐ Popular amenities Pool, Air conditioning and Internet
🐾 Pet friendly rentals 763 properties
🏊 Holiday rentals with pools 1,492 properties

Frequently Asked Questions

What is the price per night for a holiday rental in Islamorada?

The average starting price for a holiday cottage or rental in Islamorada is £88 per night. Prices vary depending on the type of holiday let, season, and amenities. Check HomeToGo to see current rates and discounts.

How many holiday lettings are available to rent in Islamorada? And what are the most popular types of holiday lets?

There are currently 1,827 holiday apartments from 17 different providers on offer in Islamorada. More than half of holiday rentals in Islamorada are house rentals, making them a top pick among travellers. They’re ideal whether you’re planning a romantic escape or a group getaway. Discover the most booked options quickly with HomeToGo’s smart filters.

What is the most searched holiday rental amenity in Islamorada?

Travellers planning trips to Islamorada usually search for Pool, Air conditioning, and Internet when it comes to holiday rental amenities.

Do you offer holiday homes with a swimming pool in Islamorada?

Yes, 82% of holiday homes in Islamorada come with a swimming pool. With 1,492 properties available, it’s a popular choice for those looking to unwind or entertain. Find your perfect poolside getaway on HomeToGo.

Are there any pet-friendly holiday cottages in Islamorada?

Absolutely! Pet-friendly holiday rentals in Islamorada are widely available. So your furry friend doesn’t have to miss out on the adventure. Use HomeToGo’s filters to find the perfect pet-friendly stay.

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

Sun lovers should visit Islamorada in July and August to enjoy the warmest weather.

Where can I see discounts on holiday accommmodation in Islamorada?

You can get great value holiday rentals in Islamorada with prices for a letting beginning at £88 - and HomeToGo has launched plenty of features that mean it's a piece of cake to see the top deals. When considering different dates for your break, search with HomeToGo's flexible dates technology to easily look for lower cost date options and see discounts of up to 10%. Moreover, HomeToGo's 'distance from' filter makes it easy to uncover hidden treasure holiday rentals in great value, lesser-known locales that are just as close to the area of your choice, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Start your search as soon as possible to get the best of the greatest variety of options and low prices - and do so without worries by ticking HomeToGo's 'free cancellation' filter when searching for holiday accommodation.

What are the advantages of choosing a holiday letting in Islamorada with HomeToGo?

From increased privacy away from the crowds to more space in which to chill out with your family, friends or partner, holiday lets in Islamorada provide plenty of benefits. HomeToGo shows you genuine ratings from verified visitors, and searching is secure, easy, and stress-free - so with 1,827 lettings from 17 providers in the area, you're sure to locate the right place to stay with all of the amenities you need in Islamorada.

Do you offer holiday accommodation for couples in Islamorada?

There are lovely holiday homes in Islamorada designed with couples in mind. Enjoy a romantic retreat with just the right amount of space and charm. HomeToGo helps you discover the best spots for two.

Can I book a waterfront holiday rental in Islamorada?

Yes, there are 1817 waterfront holiday lets available in Islamorada. Staying close to the water is ideal for scenic views and a relaxing atmosphere. Use HomeToGo’s "Near the water" filter to find your perfect waterfront holiday let.

Why should I book my holiday rental with HomeToGo?

From seaside cottages to city apartments, HomeToGo has the best holiday rentals out there. You’ll enjoy a simple booking process, local expertise, and top prices from trusted providers. Your next great stay is just a few clicks away.

Can I find family-friendly holiday lettings in Islamorada?

You’ll find family-ready holiday rentals in Islamorada that cater to groups. You’ll find options for every budget and family size. Use HomeToGo to explore family-friendly holiday cottages with ease.

Can I cancel my holiday rental booking for free?

Worried about changes? Plenty of holiday rentals listed on HomeToGo come with free cancellation options. Look for rentals with free cancellation to keep things stress-free.

Is it possible to rent a holiday home for a weekend getaway in Islamorada?

Yes, weekend breaks are easy to plan with flexible holiday rentals in Islamorada. Many homes offer short stays without long commitments. Find yours easily on HomeToGo.

Are there any last-minute holiday rental deals in Islamorada?

There are plenty of last-minute holiday homes in Islamorada available at reduced prices. With HomeToGo, you can find great value — and save up to 10%, even at short notice. Use HomeToGo’s filters to see what’s available right now.

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