See all properties

Best location in downtown Islamorada. 2 Houses with Beach access!

Living area

Living area

Living area

Private kitchen

Private kitchen

Don't miss out! Price and availability may change

House in Upper Matecumbe Key, FL

18 guests · 6 bedrooms · 5 baths

Reasons to book

Great for petsBring all your friends and family, even the furry ones

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. This listing is for 2 houses - 1 property. The 2 homes are right next to each other offering plenty of space for your group getaway. Walk to the beach and walk or bike to great restaurants, marinas and shopping. The beach is a 2 minute walk down the street as well as the famous Islamorada Brewing Co! The home comfortably sleeps 10 people. We are a local family who is happy to help with your Island Getaway!

Amenities

Non-smoking

Pets allowed

Family friendly

Map of Upper Matecumbe Key, FL

city location on map

Nearby attractions

Everglades National Park

Everglades Alligator Farm

Florida Keys Aquarium Encounters

Theater of the Sea

$$$$

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Best location in downtown Islamorada. 2 Houses with Beach access!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Best location in downtown Islamorada. 2 Houses with Beach access! pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Best location in downtown Islamorada. 2 Houses with Beach access!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.

Explore similar stays in Upper Matecumbe Key

Explore all stays

9.8 / 10

Outstanding(9 Ratings)

Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!

6 guests · 3 bedrooms · 3 baths

Villa in Upper Matecumbe Key, for $760 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

You can save with One Key

Relaxing Garden Suite With Pool @Islamorada- Sea Turtle Suite

3 guests · 1 bedroom · 1 bath

Business stays, family stays, couples stay, getaway vacation, and rental in Upper Matecumbe Key at Relaxing Garden Suite With Pool @Islamorada- Sea Turtle Suite for $2,415 for your next trip.

8.7 / 10

Excellent(1,507 Ratings)

Sunset Inn

2 guests · 1 bedroom · 1 bath

Free WiFi/internet · Air conditioning · Pool

The best choice in Upper Matecumbe Key for Hotel, for $549 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Relaxing Garden Suite With Pool @Islamorada- Sea Turtle Suite

3 guests · 1 bedroom · 1 bath

Looking for a memorable stay in Upper Matecumbe Key? Our Hotel might just be what you're looking for. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more during your stay.

8.6 / 10

Excellent(670 Ratings)

Sunset Inn

Hotel

in Islamorada

3star

2 guests · 1 bedroom · 1 bath

Free WiFi/internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our Hotel in Upper Matecumbe Key has everything you need for a rejuvenating stay. Treat yourself to Sunset Inn's exceptional amenities, such as Free Parking, Pool and Garden.

10 / 10

Outstanding(2 Ratings)

Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only

6 guests · 3 bedrooms · 3 baths

Looking for the perfect place to call home during your trip to Upper Matecumbe Key? This Villa offers a comfort and style with top-notch amenities, including Pets allowed, Family friendly and Non-smoking, and more.

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

3 guests · 1 bedroom · 1 bath

Looking for the perfect place to call home during your trip to Upper Matecumbe Key? This Hotel offers a comfort and style with top-notch amenities, including Pets allowed, Family friendly and Non-smoking, and more.

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

3 guests · 1 bedroom · 1 bath

Soak up the beauty of Upper Matecumbe Key in our Hotel, Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite. With a range of amenities such as Pets allowed, Family friendly and Non-smoking, you'll feel right at home.

Upper Matecumbe Key travel inspiration

The Best American Lake Town Awards 2026: Where Shoreline Meets Soul

America’s Best Hidden Beach Towns (2026 Awards)

Best Small Towns for Spring Getaways (2026)

The Ultimate Packing List For Your Vacation (2026)

Where Everyone Knows Your Name: America’s Most Welcoming Small Towns (2026)

35 Road Trip Necessities for the Perfect Journey

How to Pack a Suitcase: 12 Steps to Perfect Packing

Top 25 Packing Tips for 2026 (Smarter, Lighter, Stress-Free Travel)

Keep exploring