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5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Top rated by guests
Exterior
bathroom #4
bathroom #3
Style of Every Shower
panoramic of bedroom #4 - Master Suite
review stars
10Outstanding
(132 Ratings)
"This home was wonderful and offered easy boat access to the Gulf, making it the perfect place for our stay. We really appreciated all of the owners’ personal recommendations for places to shop and eat..."
Josh N.
Don't miss out! Price and availability may change
10 / 10
Outstanding(132 Ratings)

House in Upper Matecumbe Key, FL

10 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental

Deep water dockage & heated pool!

Modern, clean & fresh interiors make this rental perfect.
Manatees visit the dock daily - they are sweet, gentle giants!
Dock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use.

This Bayside house with a gorgeous heated pool and deep water is centrally located in the heart of the Village of Islamorada. The house is walking distance to the most of what makes Islamorada so special. It is only a 1/2 block from famous Lorelei Cabana Bar & Restaurant and 1/2 block from the Casa Morada Hotel. Large open living/dining/ kitchen area overlooking a partial view of open ocean on Bayside. Back Country Fishing is minutes away as the house sits only one property from open ocean. It has 3 master suites with king each, 1 king bedroom and 1 additional bedroom with twin beds.

Modern, clean & fresh interiors make this rental perfect.
Manatees visit the dock daily - they are sweet, gentle giants!
Dock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use. The waterfront pool is heated to 86 degrees.

Plenty of boat trailer parking onsite.

THIS PROPERTY RENTS SATURDAY TO SATURDAY - we might make exceptions but during high season we have Saturday to Saturday bookings only.

Islamorarda has so much to offer, amazing restaurants, aqua blue waters, incredible fishing and boating!
The restaurants within walking distance: Lorelei Restaurant, Islamorada Beer Company, Morada Bay Beach Café, Pierre's Chef Michael's, Kaiyo Grill, Keys Brewery, Bayside Gourmet, Bayside Gourmet, Bitton Bistro and Mangrove Mike’s.


About the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel ; it is exceptionally clean and easy to enjoy.

We privately own a total of 5 boutique vacation rentals in Islamorada:
VRBO listing #1576833 (5 bedroom)
VRBO listing #1054019 (5 bedroom)
VRBO listing #1977457 (7 bedroom)
VRBO listing #689629 (5 bedroom)

LICENSE #: 26-0278 - Islamorada

Amenities at 5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Non-smoking
No pets allowed
Family friendly

Map of Upper Matecumbe Key, FL

city location on map

Ratings and reviews

10 / 10
Outstanding(132 Ratings)
10 / 10Outstanding·Jun 2026
This home was wonderful and offered easy boat access to the Gulf, making it the perfect place for our stay. We really appreciated all of the owners’ personal recommendations for places to shop and eat. They made exploring the area even more enjoyable.We loved fishing from the dock, where we were treated to several manatee visits, and had a great time using the kayaks and paddleboards that were provided. After long days out on the water, the pool was the perfect place to unwind. We had a fantastic stay and would gladly return!
10 / 10Outstanding·Jun 2026
2nd time I have rented this property. Fantastic property as well as the host. Will definitely rent again and recommend. Thanks for a great week.
10 / 10Outstanding·Jun 2026
We’ve stayed here in the past, and hope to continue in the future - clean, comfortable, in the perfect Islamorada location on a protected cove, with a tremendous host! Bring the boat, fishing & dive gear, and the house has everything else, to include a great pool & outside area, plenty of parking, a short walk to restaurants & bars, and even a deep freezer for bait, etc. Thank you Chausey for another fantastic family vacation!
10 / 10Outstanding·Mar 2026
⸻We had an amazing week at this property! The house and grounds were exactly as described—clean, well-maintained, and beautifully situated with stunning bay views.The heated pool was perfect, and the kayaks and fire pit were a huge hit with our group. We especially loved being able to fish right off the dock, and it was incredibly easy getting our rental boat in and out.The location couldn’t have been better—close to great restaurants, a brewery, and Publix—yet still quiet and private. It truly offered the best of both convenience and relaxation.We thoroughly enjoyed our stay and are already looking forward to renting again!
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at 5 bedroom - Deep Dockage & Heated Pool in Islamorada.. 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 5 bedroom - Deep Dockage & Heated Pool in Islamorada. pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at 5 bedroom - Deep Dockage & Heated Pool in Islamorada.?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.