Title: Windley Key Pet-friendly Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windley Key Pet-friendly Vacations

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## Top Pet-friendly vacation packages in Windley Key

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

![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Solé Miami, A Noble House Resort

Ocean Four

Save 100% on your flight

$577

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,935 reviews)

Staff were nice. There's just not much in the area and have to uber everywhere

Reviewed on Feb 22, 2026

![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/f8e7300f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### W South Beach

South Beach

$3,317

per person

May 1 - May 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

Room was Amazing very clean! Staff everywhere was welcoming and friendly

Reviewed on Feb 8, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,115

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/7ff98ba1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Miami Beach

Mid Beach

$907

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,120 reviews)

Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on Feb 19, 2026

![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pelican Hotel

South Beach

Save 100% on your flight

$680

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

Great cozy old hotel, location is very good, the restaurant and foods awesome, they made a mix up in our first included breakfast and took me a long time of argument with the hotel manager to convince him for their lack of information and to get my money back, that and 40 minutes waiting to get my car back from valet are the only reason to give them 4 stars otherwise the stay was pleasant

Reviewed on Feb 24, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Pet-friendly vacations in Windley Key

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

![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### EAST Miami Residences

Brickell

$1,316

per person

May 15 - May 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (84 reviews)

Es la 3 vez que me hospedo y es excelente el trato, la hubicacion y las fascilidades.

Reviewed on Jan 26, 2026

![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/f8e7300f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### W South Beach

South Beach

$3,317

per person

May 1 - May 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

Room was Amazing very clean! Staff everywhere was welcoming and friendly

Reviewed on Feb 8, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,115

per person

May 10 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly vacations in Windley Key

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/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$528

per person

May 6 - May 9

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Our favorite part was the Rum Runner boat taxi. Captain Jen and Mate Bruce weee wonderful.

Reviewed on Feb 21, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,772

per person

Apr 4 - Apr 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/7ff98ba1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$651

per person

Apr 4 - Apr 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,120 reviews)

Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on Feb 19, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly vacations in Windley Key

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

$502

per person

May 12 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Room was small but clean.

Reviewed on Feb 26, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

$1,939

per person

May 18 - May 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (311 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/f8e7300f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### W South Beach

South Beach

$3,317

per person

May 1 - May 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

Room was Amazing very clean! Staff everywhere was welcoming and friendly

Reviewed on Feb 8, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Top Pet-friendly Windley Key Hotels

![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

This family-friendly, oceanfront resort welcomes dogs (fees apply) with pet-friendly perks such as food and water bowls. While you're here, explore nearby hiking ...

9/10 Wonderful! (157 reviews)

All was fantastic. Very nice staff. Clean room. Highly recommended

Reviewed on Feb 23, 2026

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

![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

- 6 min walk from Theater of the Sea

Dogs are welcome to join you (fees apply) for a pet-friendly getaway at this family-friendly, oceanfront motel.

8.4/10 Very Good! (1,001 reviews)

The room was spacious and clean with a nice view of the ocean. Unfortunately, our weeks stay was marred by the arctic freeze up and down the east coast. We were unable to access the "heated pool" nor go into the ocean. The clerk at the desk is very friendly. The pillows in our unit were dead. There ...

Reviewed on Feb 25, 2026

[](https://expedia.com/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information)

![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL

- 8 min walk from Theater of the Sea

Hiking and biking trails are ready for you to explore near this oceanfront hotel, where dogs can stay for an additional fee.

8.8/10 Excellent! (1,000 reviews)

My stay at Drop Harbor was excellent. The room was spotless and the location couldn’t have been better. I opened my door and the water was right there — absolutely beautiful. The front desk staff was very friendly and welcoming. Overall, a fantastic experience!

Reviewed on Feb 24, 2026

[](https://expedia.com/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information)

[See all 2,741 properties in Windley Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976197663)

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 Vacation Ideas

[Flights to Windley Key

](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[

Windley Key Hotels

](https://expedia.com/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[

Vacation Rentals in Windley Key

](https://expedia.com/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[

Car Rentals in Windley Key

](https://expedia.com/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[

Windley Key Vacations

](https://expedia.com/Windley-Key.d553248635976197663.Destination-Travel-Guides)[

Things to do in Windley Key

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