Title: Beach Vacations in Islamorada 2026 | Expedia.ca

![](https://images.trvl-media.com/place/10768/fc4588ee-e7f3-44af-8fce-e7aa6a494cda.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Islamorada Beach Vacations

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Flight and Beach hotel deals in Islamorada

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

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $1,379

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (108 reviews)

Spotless room, friendly staff, excellent food

Reviewed on Feb 6, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $1,744

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.

Reviewed on Feb 9, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $3,240

per person

Mar 13 - Mar 20

found 13 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 2026

![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Islander Resort

Matecumbe

CA $2,841

per person

Apr 21 - Apr 26

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

Great room facing ocean..sweet sitting area out front

Reviewed on Feb 10, 2026

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Amara Cay Resort

Matecumbe

CA $3,001

per person

Mar 13 - Mar 20

found 13 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,252 reviews)

Great staff, good view from room and breakfast was superb. Thanks.

Reviewed on Feb 10, 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/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Beach holidays in Islamorada

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $1,744

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.

Reviewed on Feb 9, 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/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Beach holidays in Islamorada

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

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $1,379

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (108 reviews)

Spotless room, friendly staff, excellent food

Reviewed on Feb 6, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $1,744

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.

Reviewed on Feb 9, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $1,615

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 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/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Beach holidays in Islamorada

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

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

CA $1,211

per person

Mar 17 - Mar 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $3,181

per person

Mar 17 - Mar 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.

Reviewed on Feb 9, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

CA $1,455

per person

Apr 20 - Apr 24

found 16 hours ago

Roundtrip non-stop flight included

Windsor (YQG) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

excellent location very nice simple breakfast close to liz’s of activities great poool

Reviewed on Feb 2, 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/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Find the best beach vacations in Islamorada

####  What are some benefits when booking beach vacations in Islamorada? 

When you travel to the beach in Islamorada, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. 
  
####  How can I book the best beach vacations in Islamorada? 

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Islamorada trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. 

####  Can I book cheap beach vacations in Islamorada? 

There are quite a few things you can do to get cheap beach vacations in Islamorada. Prices range from CA $1,211, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. 

####  Can I book beach packages? 

Yes, and you'll find quite a few beach packages available in Islamorada. These package deals let you save by booking your accommodation and your flight together with savings of up to 22\. 

####  Why should I book family beach vacations? 

When you're travelling with the family to Islamorada, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. 

####  How can I find a beachfront vacation in Islamorada? 

It's easy to find a beachfront vacation accommodation in Islamorada using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

####  How can I book last-minute beach vacations? 

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Islamorada as your destination and see what's available. 

####  Can I find all-inclusive beach vacations ? 

Yes, all you have to do to find all-inclusive beach vacations in Islamorada is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. 

####  Can I book a beach trip that's fully refundable? 

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Florida. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

####  Why should I book beach vacations with Expedia? 

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

## Beach 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! (1,675 reviews)

Nice stay

Reviewed on Feb 10, 2026

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

- 8 min drive from Theater of the Sea

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,296 reviews)

Paradise away from Home!! Thank you!

Reviewed on Feb 7, 2026

[](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

84001 Overseas Hwy Islamorada FL

- 10 min walk from Theater of the Sea

Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (143 reviews)

Spotless room, friendly staff, excellent food

Reviewed on Feb 6, 2026

[](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information)

[See all 2,218 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.

## More vacations you might like

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Top Beach Vacation Destinations

> - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach)
> - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach)
> - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida)
> - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados)
> - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach)
> - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach)
> - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach)
> - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach)
> - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach)
> - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India)
> - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach)
> - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario)
> - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada)
> - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona)
> - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach)
> - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal)
> - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy)
> - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand)
> - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France)

## 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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app