Skip to main content
Entire home

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Photo gallery for 5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Outdoor pool, a heated pool - 5 bedroom - Deep Dockage & Heated Pool in Islamorada. (Islamorada)
Property grounds - 5 bedroom - Deep Dockage & Heated Pool in Islamorada. (Islamorada)
Exterior - 5 bedroom - Deep Dockage & Heated Pool in Islamorada. (Islamorada)
Smart TV - 5 bedroom - Deep Dockage & Heated Pool in Islamorada. (Islamorada)
Interior - 5 bedroom - Deep Dockage & Heated Pool in Islamorada. (Islamorada)
In the heart of Islamorada Village, this Bayside house offers a perfect blend of relaxation and adventure. Take a short walk to famous Lorelei Cabana Bar & Restaurant or unwind in the heated pool overlooking partial ocean views.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 102200 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

About this property

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

  • 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

Property amenities

Beach

  • Beach loungers

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchenette
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • No lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In the city centre
  • Near a hospital
  • Near a zoo
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Heated pool
  • Kayak
  • Paddleboard
  • Water sports equipment
  • Birdwatching nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 2,200 square feet

Similar properties

Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort
Matecumbe
  • On private beach
  • Pool
  • Breakfast included
  • Pet-friendly
9.2 out of 10, Wonderful, 1,727 reviews
The price is £191
includes taxes & fees
2 Aug - 3 Aug
Chesapeake Beach Resort
Compare similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Absolutely no smoking

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have any lifts

About the area

Located on the waterfront, this holiday home is in Matecumbe, a neighbourhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. With jet skiing, kayaking and scuba diving nearby, you'll find plenty of adventures in the water. Visit our Islamorada travel guide
View more Holiday homes in Islamorada
Map
Islamorada, FL

What's nearby

  • A church sign with the name Matecumbe United Methodist Church, listing Sunday School and Worship Service times.
    Matecumbe United Methodist Church
    9 min walk - 0.5 miles
  • A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.
    Florida Keys Brewing Co.
    14 min walk - 0.8 miles
  • Islamorada Brewery & Distillery
    6 min walk - 0.4 miles
  • Keys History & Discovery Center
    6 min walk - 0.4 miles
  • beach near Islamorada
    7 min walk - 0.4 miles

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon)
    39 min drive

Restaurants

  • Lorelei Restaurant & Cabana Bar
    2 min walk
  • Wendy's
    3 min walk
  • Islamorada Fish Company
    17 min walk
  • Bayside Gourmet of Islamorada
    12 min walk
  • The Whistle Stop Pub & Grill
    10 min walk

Frequently asked questions

Does 5 bedroom - Deep Dockage & Heated Pool in Islamorada. have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is 5 bedroom - Deep Dockage & Heated Pool in Islamorada. pet-friendly?

No, pets are not allowed at this property.

How much is parking at 5 bedroom - Deep Dockage & Heated Pool in Islamorada.?

On-site parking is available at the property.

What time is check-in at 5 bedroom - Deep Dockage & Heated Pool in Islamorada.?

Check-in begins at 4:00 PM.

What time is check-out at 5 bedroom - Deep Dockage & Heated Pool in Islamorada.?

Checkout is at 10:00 AM.

Where is 5 bedroom - Deep Dockage & Heated Pool in Islamorada. located?

Located in Matecumbe, this holiday home is within a 10-minute walk of Lorelei Restaurant & Cabana Bar, Keys History & Discovery Center and Islamorada Brewery & Distillery. Matecumbe United Methodist Church and Florida Keys Brewing Co. are also within 15 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

5 bedroom - Deep Dockage & Heated Pool in Islamorada. Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 125 out of 128 reviews
Rating 8 - Good. 3 out of 128 reviews
Rating 6 - Okay. 0 out of 128 reviews
Rating 4 - Poor. 0 out of 128 reviews
Rating 2 - Terrible. 0 out of 128 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Linda B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Family Vacay!

Our family all thought this was the perfect spot for our famuly vacation
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Kate T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Spot

Great house, have booked a couple times now. Always has a new improvement. Fabulous location. Willl be back!
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Peter O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed at this property over the Christmas holidays (2025) and cannot say how happy we were with the house, owner, and location.Location: We explored other Keys but found this location to be perfect. Near Publix, restaurants (although we ate in most nights), Lorelei was just down the block, and less than a two hour drive from Miami International. House: very clean and spacious. Plenty of bedrooms that fit our family (my wife and I, four grown children and two significant others). The kitchen was well equipped (with additional items added by the owner after we inquired). We used the pool everyday and our kids fished off the dock everyday (and we also saw a mother and baby manatee).Owner: Chausey was great. She was extremely responsive and added items upon inquiry (Christmas tree, roasting pan). Thanks Chausey!It was such a hit with our family, we hope to stay here again next year!
Stayed 10 nights in Dec 2025
Verified

10/10 Excellent

Keith C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada paradise

Great place to stay awesome location for a boat 42 freeman was able to dock!!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Michelle M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Property was excellent

House was clean , great location and homeowner was fantastic
Stayed 7 nights in Jan 2024
Verified

10/10 Excellent

Jeff P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Host, Absolutely Perfect Property for my Family!!

Beautiful bay views, manatees galore, fishing off the sea wall, enough dockage for our 22 & 18 ft boats. 3 excellent master suites with great bathroom showers. Kitchen, dining room and family room all open to each other and great for gathering. Perfect pool, waterside chairs & firepit.Highly recommend!!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Julie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular Spring Break

We had an awesome stay at this property. The location of the house is amazing and walkable to many bars and restaurants. We used the kayaks and paddleboards daily and were visited by manatees a few times during our week. The pool was the perfect temp! The property manager was very responsive to questions before & during our stay. Highly recommend!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Rae S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Favorite Place to Stay

We have rented this house twice now. We loved it so much, we referred friends to stay. The house has the perfect location on the island to walk or bike places including stores, restaurants, and shopping. The house itself along with the pool and dock offers everything you need to relax and enjoy Islamorada! Only a 1 minute walk to Lorelei which we love! Staying again next year!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Karen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Getaway

Our weeklong stay here was perfect. We enjoyed the ocean view and a visit from a manatee. The pool area and bonfire were a great way to enjoy the day and evening. We also rented a boat for the week to do some sightseeing and fishing so this place worked perfectly for this activity. The paddle boats and kayaks were a hit too. Thanks for sharing your beautiful home.
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Lindsay S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Return to Paradise

This is our 2nd stay at this amazing home. Everything was perfect! This vacation rental has everything you could need for a fabulous stay in Islamorada!!! Excellent location for dining and well as a quick boat ride out to the sandbar. Our teens spent hours catching fish from the dock! Periodic visits from the local manatees was spectacular. We can’t wait to return to paradise next year!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Rich L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and location

Perfect home for family. Loved the location. The pool was terrific! We caught fish off the dock, saw the manatees each day, kayaked and paddle boarded. Overall an outstanding experience.
Stayed 7 nights in Dec 2023
Verified

10/10 Excellent

LORI W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect 3 Family Home

With 3 master suites plus 2 bdrms, this house is perfect for our entire family! Spacious main living area- beautiful water view! Deep water dockage & easy access are great. Another beautiful family vacay ! Owner very responsive.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Erica L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

We spent my 50th birthday and celebrated our son’s high school graduation. The house was perfect for 2 families with teenagers as everyone had their own space. It accommodated our boat and need to be in the middle of all the action as well as access to the water. The pool was an added bonus! Will definitely recommend this property and come back.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Brian S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding in the Keys

My daughter got married in Islamorada (Destination wedding) and we needed a large home to accommodate family. This place was perfect. We had a boat and 2 jet skis and the dock accommodated all very easy. The house is well stocked and had paddle boards and sea kayaks. The young people loved them. We saw Manatees everyday at the dock, dolphins even came in one day. Beautiful home made for a grand wedding and vacation. Thank you!
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Sam P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great host, perfect location, & amazing stay in Islamorada

We had an amazing week at Manatee Bayside Dock House! The home was impeccably clean and linens were fresh and new. The views are unbeatable, and the boat dock was a major perk, as we trailered our own boat. We spent the week enjoying boating, fishing, paddle boarding, kayaking and dipping in the pool. We walked everywhere- restaurants and local shops- the location cannot be beat! We met some local friends too- manatees, sharks, and iguanas. We are looking forward to our next adventure with @SwaySouth rentals! Thanks for an amazing week.
Stayed 7 nights in Nov 2024
Verified

10/10 Excellent

Scott W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another Amazing Stay!

This is our 2nd year in a row staying in one of Chausey’s properties, and like last year, it was once again perfect! From booking, to check-in through check out, Chausey’s communication & support was on point, ensuring we had everything for an amazing stay. The house is immaculate & fully stocked, and whether fishing, diving, relaxing, or catching happy hour or dinner at one of the nearby restaurants & breweries, the location cannot be beat! And for the boaters - the basin is deep, protected, with a great dock, cleaning station, and shed with deep freezer for all the gear. The host & house has our highest recommendation…..we will absolutely be booking again!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Lindsay S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Villa Paradise

This home is one of the best places we have rented in Islamorada. The location is right in the middle of everything. The view is spectacular with easy access to the bay. We were able to keep our 36' Pursuit right our front. The canal has an amazing family of manatee that we saw every day as well as the kids had a blast catch/release fishing from the dock. The home is very well appointed and had everything we needed for an amazing week. Very clean and neat! We will returning next year!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Marian F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay

We had an amazing stay with our annual family vacation! There was a total of 10 of us, kids included. We have plenty of room for all of us. The house had very nice water views. We trailed our 27’ boat and the dock area was perfect! Deep enough area to get the boat in/out of without worrying about the tides. The kids kept occupied with the kayaks and paddle boards. Manatee visited several times during the week! The house is conveniently located to restaurants and the local Publix! The beds were very comfortable. Our check-in/check-out was flawless. We will definitely stay there again!!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

cary c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing VRBO!

I cannot say enough good things about this house. I had my family and friends down this past week, and we had a wonderful vacation. The house was very nice, and the amenities were terrific. It is set up perfectly to host a large group in Islamorada. They thought of everything you would need. If you like to fish this is the PERFECT place to stay. Washdown equipment, floating dock, and large freezer- if you need it, this place has it. And the location is perfect. Need to stop at Bass Pro in the am? No problem, it's a 5 min idle. We will definitely be staying here again. Lastly, Chausey, the manager, is amazing. Super responsive and professional in all respects. It's expensive, but like most things in life, you get what you pay for, and this place delivers.
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Pam F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
⸻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!
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Diana W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing stay in the House. Everything was perfect, the owner was very nice and helpful.
Stayed 9 nights in Oct 2025
Verified

10/10 Excellent

Elizabeth H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic house and property! Wonderful location! Would definitely stay here again.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Keith M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Karen Ann B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved everything about our stay, especially the details our host Chausey helped us with. The pool was cozy warm for old and young, our kids fished off the dock of plenty. Groupers, angel fish, nurse sharks, mud sharks, they just kept coming. The local shopping, music, bars, just the best location! Chausey made sure our group had enough paddle boards and kayaks. We made alot of good memories!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Gary M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is great and location couldn’t be better. Very close to a lot of restaurants, breweries and easy in and out with the boat. 5bdrms 4 bath was perfect for us. Got to meet an adult manatee and a juvenile manatee as well. Owners are awesome, got to meet them as well and communication prior to and during trip was great.
Stayed 7 nights in Aug 2025