Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach

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Entire home

Entry and Walk Up to Pirate Point Main House

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms5 bathroomsSleeps 103500 sq ft

Popular amenities

Parking available
Air conditioning
Dryer
Pet-friendly
Washer
Pool

Explore the area

Marathon, FL

Coco Plum Beach
‪17 min walk‬
Curry Hammock State Park
‪1 min drive‬
Sombrero Beach
‪17 min drive‬
Marathon, FL (MTH-Florida Keys Marathon)
‪9 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Ahoy Suite

1 King Bed

Blackbeard Suite

1 King Bed

Sea Dog Suite

1 Queen Bed

Shipwreck Suite

1 Queen Bed

Treasure Master Suite

1 King Bed

5 bathrooms

Ahoy Suite

Toilet · Shower only

Blackbeard Suite

Toilet · Shower only

Hall Bathroom

Toilet · Shower only

Seadog House Bathroom

Toilet · Shower only

Treasure Suite

Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Garden

Dining area

About this property

Welcome to Pirate Point – your private slice of paradise. Tucked away at the end of a peaceful canal street on lush, landscaped grounds, this upscale waterfront estate offers the ultimate blend of luxury and comfort. Set on nearly an acre at the corner of Avenue G canal and Coco Plum Bay, the compound boasts expansive bay views, a private dock, and exceptional outdoor living spaces.

The property includes a 3BR/3BA main home, a separate 1BR/1BA apartment, and a detached 1BR suite — offering ideal flexibility for families or groups who crave both connection and a bit of separation. Inside, coastal-chic interiors and a spacious open-plan great room invite you to unwind, while outside you’ll find a sparkling private pool, hammocks, a dockside tiki lounge, and game areas — all designed for relaxation and fun. Guests rave that Pirate Point’s charm can't be captured in photos and how right they are! The soothing waterfront vibe, tropical breezes, and peaceful seclusion create an atmosphere that must be felt to be believed.

Fish from the sea wall, enjoy sunset cocktails by the tiki, or cook up a feast in the fully stocked kitchen or pn the poolside grill. The home is perfect for multi-generational families, couples traveling together, or friends seeking a high-end Keys escape.

Part of the exclusive HappyintheKeys collection of luxury homes, Pirate Point is dog-friendly and proudly managed with care by a family-owned team dedicated to guest comfort.

Please note: For stays longer than one week, special deposit/payment terms apply. Contact us for details.

Property manager

Kim Portner

Premier Host

Languages

English, Spanish

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

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Picturesque views of the Gulf from the pool and hot tub

Pool
Kitchen
Washer
Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 9:30 AM

Children

Children allowed: ages 0–17

Both parents and/or legal guardians of all childre

Events

Events allowed: family gatherings, birthday parties, weddings

Pre approved events only.

Pets

Pets allowed: dogs (limit 2 total)

Certain Dogs Only. The following breeds, and any

Smoking

Smoking is not permitted

Guest must sign rental agreement. A Security Deposit hold (not a charge) of $500 will be placed on your credit card just before your arrival.

Any damage after your departure will be charged against the security deposit hold. No smoking at all.

Maximum occupancy of the property includes adults and children of all ages.

Important information

You need to know

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

Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 20

Note from host: Pre approved events only.

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

We should mention

A car is recommended for transport to and from this property

About the area

Marathon

Located in Marathon, this holiday home is on the waterfront. Captain Hooks Marina and Dive Center and Florida Keys Country Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sombrero Beach and Curry Hammock State Park. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.

Marathon, FL

What's nearby

Coco Plum Beach - 17 min walk - 1.4 km
Curry Hammock State Park - 1 min drive - 0.0 km
Captain Hooks Marina and Dive Center - 6 min drive - 4.0 km
Sunset Park Beach - 7 min drive - 3.4 km
Sombrero Beach - 17 min drive - 13.9 km

Getting around

Marathon, FL (MTH-Florida Keys Marathon) - 8 min drive

Restaurants

‪McDonald's - ‬10 min drive
‪Island Fish Company - ‬5 min drive
‪Wendy's - ‬10 min drive
‪Sparky's Landing Fish and Cocktails - ‬5 min drive
‪Keys Fisheries - ‬12 min drive

Frequently asked questions

Does Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc have a pool?

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

Is Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc?

Check-in begins at 4:00 PM.

What time is check-out at Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc?

Checkout is at 9:30 AM.

Where is Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc located?

Situated on the waterfront, this holiday home is 0.8 mi (1.2 km) from Coco Plum Beach and within 3 miles (5 km) of Curry Hammock State Park and Marathon Visitor Center. San Pablo Catholic Church and Captain Hooks Marina and Dive Center are also within 3 miles (5 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

10/10 Excellent

Renee M.

15 Mar, 2025

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

Excellent family house!

Beautiful property, fenced in pool and with 2 baby gates we kept 3 toddlers contained on a great patio. Every question was answered within minutes and we couldn’t have asked for a better big family gathering place

Stayed 14 nights in Mar 2025

10/10 Excellent

Robert E.

16 Dec, 2024

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

Awesome property

This is a beautiful property inside and out! Plenty of room to enjoy with friends and family and room to enjoy time alone. The owners were very easy to work with and very quick to respond to any questions. We would definitely stay again!

Stayed 7 nights in Nov 2024

10/10 Excellent

Sherry D.

5 Aug, 2024

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

Amazing

We loved this home it was very spacious and the property was beautiful. The owners were very helpful and if we had a question very prompt to get to us. Would come back again.

Stayed 14 nights in Jul 2024

10/10 Excellent

Amber C.

23 Apr, 2024

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

Beautiful stay

The property was beautiful. We all had a wonderful stay. The staff was amazing and very communicative.

Stayed 7 nights in Apr 2024

10/10 Excellent

Marcie K.

15 Mar, 2024

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

Great keys experience!

The property was very large and had room for the 8 adults to spread out and still come together. Having a boat is a must for this property although we saw manatee and dolphins almost daily. beautiful sunrises and sunsets and biking around the neighborhood was great as well. The pool is nice but the beach nearby was full of seaweed and not a place we spent time which is why the boat is very important if you want to be out on the water. The 4 king rooms all have an en suite bathroom which is great for 4 couples. Linens were not great quality but kitchen is very well stocked.Overall a wonderful experience and great property!

Stayed 7 nights in Mar 2024

10/10 Excellent

Dee N.

5 Mar, 2024

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

Fun in the sun

The accommodations were as described and the environment was welcoming and comfortable. The kitchen was well stocked with all of the cooking, dining and utensils needed. Management was very responsive to any questions or issues we had, which were minimal, mainly getting familiar with features of the home. Would definitely stay there again and would recommend it to our friends. One of the most beautiful rentals we have ever had from our travels.

Stayed 7 nights in Feb 2024

10/10 Excellent

don m.

20 Feb, 2024

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

Old folks boggie

Great resort like house and surroundings for fun time with friends and family.

Stayed 7 nights in Feb 2024

10/10 Excellent

Veronica B., Virginia Beach

9 Jan, 2024

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

We loved being on one level!

This property is perfection! You could tell that the designers were definitely into details ~ everything was decorated with up to date furnishings, cookware, towels and bed linens. I saw some of the cutest throw pillows I've ever seen!! We even had Christmas decorations and a lighted palm tree near our dining table!! We rented a large pontoon boat that we all enjoyed. The pool was very warm and clean. Our bedrooms had plenty of space to spread out and a huge kitchen/great room plus a game room that the grandkids loved! The sunsets were amazing every single day!! Highly recommend!!

Stayed 7 nights in Dec 2023

10/10 Excellent

Betsey A., Holland, MI

25 Nov, 2023

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

Amazing!! Rent this Place, you will not regret it!

Pirates Point was an incredible rental! We spent a week at pirates point and celebrated our parents 50th anniversary over Thanksgiving. We had 11 people in our party and it was the perfect space for us. There was ample seating for all of our meals in the open kitchen/great room. The kitchen was very well stocked with cooking utensils, pots/pans, mixing bowls, casserole dishes and everything you need for getting those hard-to-get crab-bites out of their shells. They even did a special delivery of extra things we might need for our Thanksgiving meal. Every space and all bedrooms were beautifully decorated, the beds were very comfortable. The bathrooms are stocked with plenty of towels and washcloths for everyone. They had a giant basket of beach/pool towels for everyone. We loved the huge sectional couch in the living room that was big enough for all of us to relax and unwind each evening together. There was also a huge outdoor sectional on the back deck and plenty of comfortable deck chairs off the living room. The home is also expansive enough that if you wanted solitude from others, it was easy to find! It was great to have a space where those that wanted to sit in the sun could and those that wanted shade could find it and both spaces have incredible views. As a collective group of 11, we couldn’t think of one thing that this property lacked! The hosts truly thought of everything. Rent this place, you will not regret it!

Stayed 8 nights in Nov 2023

10/10 Excellent

Stephanie H.

13 Aug, 2023

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

Keys getaway

We had family and friends stay together for our week at Pirates Point. The kitchen and living room were a great gathering place weather it was morning or evening and the view to the water is gorgeous! Sunsets are stunning. We love family game night so we thoroughly enjoyed using the card table to play together. AC worked great for such a hot time of year. The pool was a bit warm but that’s the time of year for anywhere in Florida. Having the 2 extra “bungalow” rooms were a bonus for family members who wanted to stay with us but have their own quiet space outside of the main house. The sea wall had plenty of boat parking and was very easy to take the boat out from the house. Overall we loved this house and would definitely stay again!

Stayed 7 nights in Aug 2023

10/10 Excellent

Jason B.

5 Aug, 2023

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

Private Oasis

Our family and friends really enjoyed Pirates Point! The beautiful private property is well kept and very accommodating for a group of 10. We all had plenty of space and privacy. The views where spectacular, the property has many amenities and is the perfect place to unwind and enjoy all the keys have to offer. Would definitely recommend.

Stayed 7 nights in Jul 2023

10/10 Excellent

Shawn M.

19 Jul, 2023

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

Great house!

We came to the area to do a bit of scuba diving and enjoyed the house so much we cancelled a few boat trips and just enjoyed hanging out together around the pool. The layout was great for us and it was by far the most thorough communication we have ever had with a house rental. Highly recommended rental property!

Stayed 7 nights in Jul 2023

10/10 Excellent

jennifer s.

8 Jun, 2023

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

Paradise in the Keys!

It was amazing. The house, the staff, the location, the views…..simply incredible!!!

Stayed 7 nights in May 2023

10/10 Excellent

Charlie P.

5 Apr, 2023

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

Wish we had just a few more days!

Best word to describe the experience was PERFECT! Happy In The Keys was the most professional, detail oriented, and serving group/individual I have ever rented from. Any question I had before or during the trip was addressed promptly, accurately, and most of all with a smile. As a business owner, it was obvious that the “experience” and customer service was priority for them. Simply put, I felt like I had my own concierge with Happy In The Keys. The house was absolutely perfect! It was a traditional Keys home with beautiful renovations. The house was SUPER clean even being pet friendly (we don’t have animals and we wouldn’t have known otherwise). Floor plan was expansive and gave our two families more from than we needed to have our own spaces. The location was ideal and the views surrounded by water were excellent. Ample outdoor area to hangout, fish, and keep your boat docked all week. This property made the vacation a vacation…super laid back and easy! The week went by way too fast, and I can usually say let’s try something different next year, but Pirate Point only left us wanting more. From start to finish, it was the perfect family vacation. It’s tough to find repeat customers, but I can say Happy In The Keys accomplished just that!

Stayed 7 nights in Mar 2023

10/10 Excellent

JESSICA W.

3 Apr, 2023

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

Beautiful and relaxing property

The property is just as amazing as the pictures. It is quiet and private, we felt like we had our own little paradise. We had two families of 4 for the week and we had plenty of space for everyone. Everything in the house was perfect (and clean), the pool was very relaxing and we saw a lot of wildlife in the canal (jellyfish, sharks, dolphins, manatee) We had a boat and enjoyed the sandbar and exploring restaurants. The surrounding area has great food and easy access to groceries as well. Very highlight recommend!!

Stayed 7 nights in Mar 2023

6/10 Okay

Dana F.

14 Mar, 2023

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

Excellent house!!

Beautiful location and beautiful place we had a great time and would definitely come back. We had 5 couples and rented a boat it was perfect close to the sand bar!

Stayed 7 nights in Mar 2023

10/10 Excellent

Lisa H.

28 Jan, 2023

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

Wonderful property for a large group

We were 5 couples, really enjoyed the house and especially the common and outdoor areas. There are 2 large gathering rooms, and we dubbed one “The Hallmark Room” when the other room had football on most of the weekend. We cooked in a fair bit, the kitchen had what we needed, and more gadgets than we used. The pool area is spacious with seating for both sun and shade available most of the afternoon. The neighborhood was easy for walking in the mornings, not a lot of traffic. Property management was attentive.

Stayed 7 nights in Jan 2023

10/10 Excellent

Colleen K.

23 Jan, 2023

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

Excellent family vacation. Truly the best.

Pirates Pointe exceeded our expectations. Property was very well maintained. Pool and docks were beautiful. We brought our boat down and enjoyed the waterways and ocean. This, by far was our best family vacation. Everything was perfect. Many memories made during our two week stay. I highly recommend this property for family’s.

Stayed 14 nights in Jan 2023

2/10 Terrible

Jeff B.

9 Jan, 2023

Liked: Check-in, location

Disliked: Cleanliness, communication, listing accuracy

Renters Beware - Don't be fooled by the pictures

House is not as advertised and is old with many issues. Cockroaches running through the house nightly and a rat dropped out of the attic access in master suite closet. Rat ran around the master suite bedroom and bathroom the entire last night. Rat traps are positioned around the exterior of the house. The wood deck and steps leading to boat well are rotten and a safety issue. "Treasure Suite" had no hot water when we arrived. There are air conditioning units on all sides of the house making it hard to hold conversations when they are running. The AC did not cool the majority of the main house. The bed frame in the apartment was broken and we got blamed for it at the end of our stay. Glass in one of the exterior doors was shattered. Exposed electrical wires in pantry. Non of these things were mentioned to us before we arrived. I don't usually write reviews but thought any future renters should know what they are getting into. Extremely disappointing experience to say the least.

Stayed 7 nights in Dec 2022

10/10 Excellent

Roy S., Cincinnati, Ohio

24 Dec, 2022

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

Pirates point

Great property. Perfect for boating. Tip lot with great views of boats going up and down canal. Only about 10 minutes to open water. Plenty of room to spread out.

Stayed 7 nights in Dec 2022

10/10 Excellent

Greg S., Lakeway, Texas

20 Dec, 2022

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

Marathon Vaca

Great Property with everything you need. Highly recommended if you have 4 couples. Good location for all the restaurants and places to visit in Marathon

Stayed 7 nights in Dec 2022

10/10 Excellent

Michael E.

3 Dec, 2022

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

Fantastic family and friend house

Pirate Pointe is hands down one of our favorite locations. We had 5 kids ranging from 13-6. They loved every moment here. The kitchen was well stocked. The beds were incredibly comfortable and the space was large enough for us to stretch out but still provided ample room to spend time together playing games. The pool is warm and inviting. My kids enjoyed swimming all day. The management team was very responsive and checked in with us throughout our stay. We would absolutely stay here again. Thank you happiness in the keys. You have a very well organized team and we enjoyed every minute.

Stayed 7 nights in Nov 2022

10/10 Excellent

Jolene B.

13 Nov, 2022

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

Lovely getaway!

This getaway was just what we were looking for. Appreciate the responsiveness of the host/property manager. Thanks for helping us have a memorable week.

Stayed 7 nights in Oct 2022

10/10 Excellent

James T., Rineyville

8 Oct, 2022

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

Paradise

We come to the Keys every year for 5 years now. This property is the best by far. The management is top notch!!!

Stayed 7 nights in Oct 2022

10/10 Excellent

Kim L.

22 Sept, 2022

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

Awesome Home!!

I have to say this was one of the best homes we've ever rented! The property is exceptional, as is the response time from the owners, Not that we had problems, but they checked in with us and the communication was seamless through the entire process and while we were there. I would HIGHLY recommend this home, and if not this home they have others in Marathon. I can't wait to go back!!

Stayed 7 nights in Sep 2022

About the host

Hosted by Kim Portner

We first visited the Florida Keys in 2009 — and it was love at first sight. The vibrant blue waters, laid-back island charm, and natural beauty captured our hearts in a way no other place had. That one trip sparked a dream: to not only put down roots here, but to create something we could share with others.

That dream became HappyintheKeys — a family-owned lifestyle brand and boutique collection of carefully curated, upscale vacation homes. What started with one home quickly grew into a small portfolio of unique, luxury residences designed for travelers who want more than just a place to stay — they want an experience.

Each of our properties reflects the spirit of the Keys: relaxing, welcoming, and full of coastal character. We take pride in thoughtful design, top-tier amenities, and the kind of attention to detail that turns a trip into a treasured memory. From the moment guests arrive, we want them to feel at home — and like they’ve discovered a slice of paradise they’ll never forget.

We're deeply involved in every home and every guest experience. When you stay at one of our HappyintheKeys properties, you’re not just booking a vacation rental — you’re joining a community of guests who return year after year for the comfort, quality, and care we’re known for.

We’re so glad you found us — and we can’t wait to share the Keys with you.

Why they chose this property

When we discovered this property, we immediately saw its potential — a rare, expansive lot with stunning water views, nestled at the end of a peaceful canal street. The land was perfect for creating unforgettable vacation experiences. But the home itself? Outdated, worn down, and in serious need of love.

So, we rolled up our sleeves and got to work. We stripped everything down to the studs and reimagined the entire space from the ground up. Every inch has been thoughtfully renovated to meet our highest standards — blending comfort, style, and functionality to create something truly special.

The result is Pirate Point: a fresh, modern retreat that honors the Keys' laid-back charm while delivering an elevated, luxurious experience. Whether you're gathering with family, reconnecting with friends, or simply escaping the everyday, this home is designed to help you unwind, recharge, and make memories that last a lifetime.

What makes this property unique

What makes Pirate Point truly stand out is its rare combination of privacy, space, and waterfront beauty — all wrapped in laid-back island luxury.

Tucked at the quiet end of a canal street, this property offers unmatched privacy and peace. With the home perched on a large corner lot surrounded by water on two sides, you're treated to expansive views of Coco Plum Bay and mangrove-lined canals — a constant connection to nature. Watch boats glide past from the windows and porches, or enjoy the soothing sway of palm trees from the hammocks at the corner of the grassy yard — a rare luxury in the Keys.

The outdoor space is a dream for both relaxation and recreation. There's plenty of decking and seating for sunbathing, dining, or sunset cocktails. The tiki hut with its cozy bench is a guest favorite — perfect for morning coffee, evening toasts, or watching dolphins and manatees pass by in the canal.

Families and groups love the thoughtful layout: large communal areas for gathering and celebration, plus quiet nooks where kids can play or adults can enjoy a moment of peace.

Fishing enthusiasts will love the extensive seawall — just grab a rod and cast off from your own backyard.

Pirate Point isn’t just a place to stay — it’s a destination. Whether you’re seeking fun-filled family adventures or peaceful tropical solitude, this home delivers a uniquely Florida Keys experience in every sense.

Languages:

English, Spanish

Premier Host

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Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach

Photo gallery for Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach

Reviews

Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 10)

Ahoy Suite

Blackbeard Suite

Sea Dog Suite

Shipwreck Suite

Treasure Master Suite

5 bathrooms

Ahoy Suite

Blackbeard Suite

Hall Bathroom

Seadog House Bathroom

Treasure Suite

Spaces

About this property