Little Bay Cottage

7 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Spa

Looking for the perfect place to call home during your trip to Upper Matecumbe Key? This Apartment offers a comfort and style with top-notch amenities, including Free Parking, Pets allowed and Gym, and more.

9.4 / 10

Outstanding(5 Ratings)

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

6 guests · 3 bedrooms · 3 baths

Looking for a Villa in Upper Matecumbe Key, this Villa for $448 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

10 / 10

Outstanding(4 Ratings)

Charming 2-bedroom open water view home in Islamorada, perfect for 6 guests.

4 guests · 2 bedrooms · 2 baths

This House for $618 in Upper Matecumbe Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

10 / 10

Outstanding(2 Ratings)

Experience the beauty of Islamorada in this 2BR upper-level with stunning water views.

4 guests · 2 bedrooms · 2 baths

This House for $615 in Upper Matecumbe Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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.

9.9 / 10

Outstanding(26 Ratings)

Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!

6 guests · 2 bedrooms · 2 baths

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

10 / 10

Outstanding(16 Ratings)

Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More

Cottage

6 guests · 2 bedrooms · 1 bath

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

You can save with One Key

10 / 10

Outstanding(17 Ratings)

The "Nest" Villa & Marina in the heart of beautiful Islamorada. Pet Friendly!

4 guests · 2 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Upper Matecumbe Key at The "Nest" Villa & Marina in the heart of beautiful Islamorada. Pet Friendly! for $608 for your next trip.

9.4 / 10

Outstanding(5 Ratings)

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

6 guests · 3 bedrooms · 3 baths

Are you ready to indulge in a relaxing getaway? Our Villa in Upper Matecumbe Key has everything you need for a rejuvenating stay. Treat yourself to Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!'s exceptional amenities, such as Family friendly and Non-smoking.

10 / 10

Outstanding(102 Ratings)

Breathtaking ocean views for your Paradise vacations

8 guests · 2 bedrooms · 2 baths

This inviting Apartment in Upper Matecumbe Key can fit your needs for many types of vacations, at $525 per night.

10 / 10

Outstanding(16 Ratings)

Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More

Cottage

6 guests · 2 bedrooms · 1 bath

Looking for a Cottage in Upper Matecumbe Key, this Cottage for $605 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

Little Bay Upper

6 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Spa

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Upper Matecumbe Key, at $549 per night for your next great vacation.

10 / 10

Outstanding(3 Ratings)

New Ground Level Caribbean Cottage

6 guests · 2 bedrooms · 2 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Upper Matecumbe Key at New Ground Level Caribbean Cottage for $533 for your next trip.

10 / 10

Outstanding(2 Ratings)

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

6 guests · 3 bedrooms · 3 baths

This inviting Villa in Upper Matecumbe Key can fit your needs for many types of vacations, at $507 per night.

You can save with One Key

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

18 guests · 6 bedrooms · 5 baths

This House in Upper Matecumbe Key, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

10 / 10

Outstanding(3 Ratings)

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

6 guests · 2 bedrooms · 1 bath

Are you ready to indulge in a relaxing getaway? Our House in Upper Matecumbe Key has everything you need for a rejuvenating stay. Treat yourself to Malayan Palm North 2 Bedrooms, 1 Bath, Garden View's exceptional amenities, such as No pets allowed, Family friendly and Non-smoking.

You can save with One Key

10 / 10

Outstanding(10 Ratings)

Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

6 guests · 3 bedrooms · 3 baths

The best choice in Upper Matecumbe Key for Villa, for $560 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

1 bedroom, 1 bath, full kitchen, 1 queen bed, 1 queen sleeper sofa.

4 guests · 1 bedroom · 1 bath

Looking for a House in Upper Matecumbe Key, this House for $507 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

10 / 10

Outstanding(104 Ratings)

Breathtaking ocean views for your Paradise vacations

8 guests · 2 bedrooms · 2 baths

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

10 / 10

Outstanding(3 Ratings)

New Ground Level Caribbean Cottage

6 guests · 2 bedrooms · 2 baths

Experience vacation in Upper Matecumbe Key with our House, New Ground Level Caribbean Cottage. Enjoy amenities such as No pets allowed, Family friendly and Non-smoking, and more.

Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside

8 guests · 2 bedrooms · 2 baths

Looking to create some memories in Upper Matecumbe Key? Look no further than our House, Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside. Enjoy top-rated amenities including No pets allowed, Family friendly and Non-smoking, and more.

Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location

6 guests · 3 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

This inviting Villa in Upper Matecumbe Key can fit your needs for many types of vacations, at $626 per night.

10 / 10

Outstanding(3 Ratings)

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

6 guests · 2 bedrooms · 1 bath

Experience vacation in Upper Matecumbe Key with our House, Malayan Palm North 2 Bedrooms, 1 Bath, Garden View. Enjoy amenities such as No pets allowed, Family friendly and Non-smoking, and more.

Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out

8 guests · 2 bedrooms · 1 bath

House in Upper Matecumbe Key, for $634 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

1 bedroom, 1 bath, full kitchen, 1 queen bed, 1 queen sleeper sofa.

4 guests · 1 bedroom · 1 bath

Looking for the perfect place to call home during your trip to Upper Matecumbe Key? This House offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside

8 guests · 2 bedrooms · 2 baths

This House in Upper Matecumbe Key, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Princess Palm North 2 Bedrooms, 2 Baths Poolside

8 guests · 2 bedrooms · 2 baths

When traveling to Upper Matecumbe Key, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $634 per night.

Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out

8 guests · 2 bedrooms · 1 bath

This House for $634 in Upper Matecumbe Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

Fish Tail Palm Ocean View 1 Queen Bed, and 1 Pull Out

4 guests · 1 bedroom · 1 bath

Discover the beauty of Upper Matecumbe Key with a stay at Fish Tail Palm Ocean View 1 Queen Bed, and 1 Pull Out, a top rated House with amenities such as No pets allowed, Family friendly and Non-smoking, and more.

Princess Palm North 2 Bedrooms, 2 Baths Poolside

8 guests · 2 bedrooms · 2 baths

Looking for a memorable stay in Upper Matecumbe Key? Our House might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.