Islamorada Beach Holidays

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Top flight + Beach hotel deals in Islamorada

Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Cheeca Lodge & Spa
Islander Resort
La Siesta Resort & Villas
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5* Beach holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
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See all available trips from New York to Islamorada
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3 Night Beach holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Cheeca Lodge & Spa
Islander Resort
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See all available trips from New York to Islamorada
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Find your perfect Islamorada beach holiday

How can I book the best beach holidays in Islamorada?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Islamorada beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in Islamorada?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Islamorada beach holidays, which start from £386. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in Islamorada?

Enjoy out-of-season seclusion on a beach holiday to Islamorada during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in Islamorada with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a Islamorada beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute Islamorada beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in Islamorada. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find Islamorada beach holidays which are all inclusive?

A beach holiday to Islamorada is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a Islamorada beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a Islamorada beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in Islamorada on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

Top Beach Islamorada Hotels

Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
  • 7 min drive from Theater of the Sea
Stay at this 4-star beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their ...
9/10 Wonderful! (1,001 reviews)

Travellers like: on the beach, cabanas, beach bars, beach towels

Travellers say...
"Everything is as described. Great environment and beautiful staying places."

Reviewed on 3 Jul 2025

Islander Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
  • 12 min drive from Theater of the Sea
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the bar in their reviews. ...
8.8/10 Excellent! (1,223 reviews)

Travellers like: on the beach, beach towels, outdoor pool

Travellers say...
"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."

Reviewed on 30 Jun 2025

Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
  • 10 min walk from Theater of the Sea
Stay at this 3.5-star beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (46 reviews)

Travellers like: on the beach, sunloungers, beach bars, beach towels

Great, but eat off property
"Property and service were great. Food was not great. Very difficult to find options for a picky eater. Had to DoorDash Wendy’s several times."

Reviewed on 2 Jul 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.