Title: Cheap Vacations in Islamorada 2026 | Expedia.ca

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# Islamorada Cheap Vacations

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## Flight and Cheap hotel deals in Islamorada

Price found within the past 48 hours. Click for updated prices.

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $905

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

We had a enjoyable stay here and would come back again if we were ever in the area.

Reviewed on Mar 24, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $2,081

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

They should have had a newsletter with activities.

Reviewed on Mar 23, 2026

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

CA $1,445

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (165 reviews)

Very, very good architectural design and construction. And a well-maintained facility.

Reviewed on Mar 23, 2026

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Amara Cay Resort

Matecumbe

CA $1,121

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,268 reviews)

Had a great stay, our second tone at this property. If have kids that want to play on the beach this Ain't the place. Water access is with stairs and during low tide its not very deep. For me and my wife just looking to relax, it was awesome

Reviewed on Mar 26, 2026

![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Islander Resort

Matecumbe

CA $1,133

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,014 reviews)

We been staying at the Islander since the early 90’s. When it was family owned. It has always been a favorite place to stay for my wife and I. Since hurricane Irma destroyed it, and it has basically been rebuilt. It was always a beautiful place, but now the landscaping foliage and updates have made the place unbelievably perfect. It offers mini golf, bocce ball, PickleBall, volleyball, shuffle board.Bikes and Kayaks our available. So there is plenty to do if you’re an active person. However, if you want to just relax there are plenty of private areas to just sit back and enjoy the ocean views on the most comfortable outdoor furniture Imaginable, that sits among the beautiful palm trees and foliage. It’s inclusive, so you never have to leave the property for your entire stay.

Reviewed on Mar 26, 2026

Don't see what you're looking for?

See all available trips from Columbus to Islamorada

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $2,081

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

They should have had a newsletter with activities.

Reviewed on Mar 23, 2026

Don't see what you're looking for?

See all available trips from Columbus to Islamorada

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $905

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

We had a enjoyable stay here and would come back again if we were ever in the area.

Reviewed on Mar 24, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $1,672

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

They should have had a newsletter with activities.

Reviewed on Mar 23, 2026

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

CA $1,445

per person

Apr 26 - Apr 29

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (165 reviews)

Very, very good architectural design and construction. And a well-maintained facility.

Reviewed on Mar 23, 2026

Don't see what you're looking for?

See all available trips from Columbus to Islamorada

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

CA $1,175

per person

May 13 - May 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

7.8/10 Good! (1,027 reviews)

Hotel is 2 separate buildings, one down the street which we were in but not notified about prior. This building appears to be under renovation without a pool or water view. All rooms are along busy, loud A1A. AC barely work and water pressure is minimal.

Reviewed on Mar 25, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $1,685

per person

Apr 30 - May 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

We had a enjoyable stay here and would come back again if we were ever in the area.

Reviewed on Mar 24, 2026

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

CA $1,729

per person

Apr 30 - May 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9/10 Wonderful! (165 reviews)

Very, very good architectural design and construction. And a well-maintained facility.

Reviewed on Mar 23, 2026

Don't see what you're looking for?

See all available trips from Columbus to Islamorada

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Cheap Hotels in Islamorada

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

- 22 min walk from Theater of the Sea

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (1,669 reviews)

Every aspect of our stay was awesome for our first time visiting The Keys. Everyone in the front office, to the people that maintained the property and guest rooms, and especially to the two gentlemen making made to order omelettes were wonderful. We loved our room and the view of the ocean was spectacular ...

Reviewed on Mar 26, 2026

[](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

[See all 2,210 properties in Islamorada](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=10768)

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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## More Vacations Ideas

[Flights to Islamorada

](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[

Islamorada Hotels

](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[

Islamorada Vacation Rentals

](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[

Islamorada Car Rentals

](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[

Islamorada Vacations

](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides)[

Things to do in Islamorada

](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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