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The Quarterdeck Cottage~Boat dockage available directly across the street

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Property grounds
Interior
Living area
Interior
Living area

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 41000 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Bokeelia, FL
  • Place, Goodwins Island
    ‪14 min walk‬
  • Place, Useppa Museum
    ‪20 min walk‬
  • Place, Key West Express
    ‪61 min drive‬
  • Airport, Fort Myers, FL (RSW-Southwest Florida Intl.)
    ‪68 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Bedroom 1

1 King Bed and 1 Double Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Outdoor play area
Garden
Dining area

About this property

The Quarterdeck Cottage~Boat dockage available directly across the street

With dockage (across the street at my privately owned property) and golf carts available for your stay (additional fee)Bring your favorite vinyl records, new record player and vinyls on site to enjoy! Come and visit my home! Once owned by a famous musician, this stunning Pine Island fishing cabin that has been recently remodeled with beautiful details! You will assess in moments Charlotte Harbor, Shell Pass, Pine Island Sound, Boca Grande Pass, Calusa Blueway Paddling Trail. The Calusa Blueway was voted as one of the top ten places to paddle board and/or kayak.

World class tarpon fishing, superb flats fishing for reds, & Snook in the mangroves, Trout in the grass, giant Sharks in the pass, Mackerel in the harbor, Grouper on the wrecks. This cottage has quick access to Shell Pass, Pine Island sound, Charlotte Harbor. There are beautiful sunrises and sunsets, and great kayaking in the area.

Brand New HIGH end quiet split unit air conditioner/heat. With WIFI and full cable, large flat screen wall mounted TV we have all the conveniences of home. A gorgeous gardenesque yard, charming night lighting, across the street from the water with dockage(I must know ahead of time as it is shared dockage with limited space)and trailer parking available, a large property and a beautiful, relaxing atmosphere. There is a king bed in the master bedroom with two door walls and there is also a pull-out sofa. Washer and dryer to keep your items clean. Come and enjoy tropical island life, relax, get some fishing in and just enjoy yourself in the beautiful sunshine. Voted one of the top fishing areas in the country. Tarpon, Redfish, Grouper, Shark, Snapper, Mackerel, Goliath Grouper, Trout, Tilapia and many many more! Several marinas just blocks away to launch your boat or for boat rentals. Charter Captains sprinkle the island and I know the best ones! Bike ride the sidewalk that extends the whole and shopping in beautiful Matlacha. Take ferries or your own boat to Cayo Costa, Sanibel, Boca Grande, Captiva, North Captiva, Useppa, or the legendary Cabbage Key to have lunch or dinner all just minutes away! Don't forget to boat past the Pine Island Sound historic cottages out on the water! Have a romantic dinner at Tarpon Lodge and sip a drink while you watch the best sun set view on the island and within walking distance!
Depending on the time of year, you may be able to enjoy some of the fresh, tropical fruit we have on the property!! Golf carts rental available at local vendors if you’d like to check into that!! So many more things to do and I can help you plan them all!

Boat/golf cart/bike/kayaks available to rent from local resources!

I have several properties all located next to one another for family or friends to vacation together yet have their own space.

All properties have WIFI, locals channels and ROKU.

OTHER PROPERTY ~

The Waterside Cottage Property ID# 7205346 Bokeelia

Please check all four properties! All unique and beautifully decorated!
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Please no inside smoking of any kind.
Recycle goes out on Wednesday/Regular garbage on Friday

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Bokeelia

Bokeelia is home to this cottage. Calusa Heritage Trail and Royal Tee Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Yucca Pens Preserve and Yucca Pens Unit State Wildlife Management Area. Tropical Breeze Fun Park and Bowland Coral Lanes are also worth visiting. Scuba diving and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
View more Cottages in BokeeliaOpens in a new window
Map
Bokeelia, FL

What's nearby

  • Goodwins Island - 14 min walk - 1.2 km
  • Useppa Museum - 20 min walk - 1.7 km
  • Edison Mall - 47 min drive - 46.5 km
  • Lee Health Sports Complex - 60 min drive - 57.7 km
  • Key West Express - 61 min drive - 57.9 km

Getting around

  • Punta Gorda Airport (PGD) - 52 min drive

Restaurants

  • ‪Street Eatz And Ale - ‬13 min drive
  • ‪7-Eleven - ‬13 min drive
  • ‪Circle K - ‬13 min drive
  • ‪Eagles Nest - ‬12 min drive
  • ‪Lazy Flamingo Bokeelia - ‬20 min walk

Frequently asked questions

Does The Quarterdeck Cottage~Boat dockage available directly across the street have a pool?

Yes, this property has a pool.

How much does it cost to stay at The Quarterdeck Cottage~Boat dockage available directly across the street?

As of Apr 12, 2026, prices found for a 1-night stay for 2 adults at The Quarterdeck Cottage~Boat dockage available directly across the street on May 24, 2026 start from $220, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is The Quarterdeck Cottage~Boat dockage available directly across the street pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at The Quarterdeck Cottage~Boat dockage available directly across the street?

Check-in begins at 4:00 PM.

What time is check-out at The Quarterdeck Cottage~Boat dockage available directly across the street?

Check-out is at 10:00 AM.

Where is The Quarterdeck Cottage~Boat dockage available directly across the street located?

Situated in Bokeelia, this cottage is within 1 mi (2 km) of Goodwins Island and Useppa Museum. Calusa Heritage Trail and Randell Research Center are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 51 out of 52 reviews
Rating 8 - Good. 1 out of 52 reviews
Rating 6 - Okay. 0 out of 52 reviews
Rating 4 - Poor. 0 out of 52 reviews
Rating 2 - Terrible. 0 out of 52 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

LEEA S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful quiet cottage…. Very clean and has everything to make your stay comfortable. Great host …. Would stay here again!!!
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Michael W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Darlene’s cozy and comfortable cottage was perfect for us. She is a fantastic host who gave us great advice on how to experience Island life.
Magical at night
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Shari W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. Darleen’s place was perfect. Beautifully decorated. It had everything we needed for our stayVery quiet neighborhood. Close to everything yet private and quaint location. We will be back.
Stayed 10 nights in Feb 2026
Verified

10/10 Excellent

MAGGIE A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at the quarter cottage. Checking in and out was no easy! Darlene is a great host, she was very helpful. The cottage was quaint and clean and had everything we needed. The location was perfect as we have family in Bokeelia. We enjoyed meals at The Lazy Flamingo, Bubbas Low Key Tiki and pizza at the Eagle's Nest.
Sunset at Pineland Pier
Captain Andy
Dolphins on the way to Costa Cayo
Random peacock on. Evening drive
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Nanette M.

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

Cute Cottage

The cottage was adorable, and had everything we needed!
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

James W.

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

Weekend getaway to Bokeelia

We love the cottage. Had an excellent time. It was very clean. Very comfortable place to stay and we won’t hesitate to go back. The host was excellent to deal with and very friendly and helpful.
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

John M.

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

Terrific place! Terrific host! Thank you Darlene! J&J

Wonderfully relaxing!
Stayed 18 nights in Mar 2022
Verified

10/10 Excellent

Benjamin C.

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

Quite and Cozy

We greatly enjoyed our stay, the area is quite and the place is clean and cozy. Really enjoyed sitting outside under the tree out front at night.
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Julie D.

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

Wonderful vacation

We had a great time! The cottage was so quaint and very clean. Darlene was a wonderful host.
Stayed 7 nights in Jan 2023
Verified

10/10 Excellent

Elizabeth M.

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

Lovely cottage with updated amenities.

Loved the property . Very easy to execute the rental., checkin & checkout Convenient location.
Stayed 2 nights in Jan 2023
Verified

10/10 Excellent

David L.

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

Charming, Comfortable House

The cottage is a very comfortable home from which to explore Pine Island's charm and scenic beauty. And be sure to sample the amazing fresh mangos!
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Clayton V.

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

Adorable

Adorable little cottage! Super clean and well appointed.
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Don K.

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

Comfort and style

We had a blast!This is a well taken care of property. The owner us very nice and responds quickly. I would stay here again.
Stayed 5 nights in Jul 2020
Verified

8/10 Good

Michael B.

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

Small but nice

The cottage was great. The owner was very attentive. The only drawback is the boat dock being across the street. The road was very busy due to the Tiki Bar at the far end. Overall it was a great place. We plan to book again at the sister property across the street.
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Samantha M.

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

Cute cottage

Excellent experience. The cottage was very cute and comfortable. We had everything we needed. Loved Pine Island - was very relaxing.
Stayed 3 nights in Feb 2023
Verified

10/10 Excellent

Kari P.

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

Quarterdeck Cottage...picture perfect

We spent five days at Darlene's Quarterdeck Cottage and we couldn't have been happier with the accommodations! Very clean, was equipped with everything we could have asked for AND the decor, mid century modern, was outstanding. We will be back again in February!
Stayed 4 nights in Oct 2023
Verified

10/10 Excellent

Jimmy B.

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

All the comforts of home.

This rental had all the comforts of home with lots of charm. It is an easy drive to St James, Matlacha, Fort Meyer, or even Sanibel Island. Or just hang out at Bookelia and enjoy a meal down at Captain Con’s on the marina. We had a wonderful stay and definitely look forward to booking again.
Stayed 5 nights in Mar 2023
Verified

10/10 Excellent

Eric A.

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

FUN IN THE SUN WITH MY SON

This was our first time to Pine Island. We had a blast fishing, riding bikes,, and using the golf cart. The house was very comfortable, and made a good place to rest and escape from the heat. Just what the doctor ordered for a long weekend.
Stayed 3 nights in Sep 2020
Verified

10/10 Excellent

Janis T.

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

Bright and cozy

We had a relaxing week at Darlene’s cottage. It was a great place, clean and well equipped and an awesome location, near the canal. The bed is comfortable, living area is spacious, kitchen is remodeled. Nice to come home to this cute place after our adventurous days. We kayaked almost every day and enjoyed the dolphins, pelicans, fishing, and beauty of this special island.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Nicole Z.

Amazing stay!!!

All we can say is wow! This was such a pleasant stay. From the welcoming hospitality to the zen house vibes, and everything you could possibly need. This place was right up our alley! We loved this little cottage, the golf cart, brand new kayaks, bikes and a cozy little screened in porch to relax out back and breathe in the fresh island air. Thanks for providing us with a great stay! We will definitely be in touch next year! Cheers!
Stayed 8 nights in Apr 2019
Verified

10/10 Excellent

joyce m.

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

Peace and Quiet

When friends and family asked “where are you staying in Florida,” we answered, on Pine Island. “Where is that?” was the frequent response. THAT was the reason we chose this location! The Quarterdeck was very comfortable, very well decorated (to our liking) and certainly made us feel welcome and at home. We LOVED the serenity of the island which allowed us to do as much as we desired, or to do nothing at all. Darlene was a great host—incredibly responsive to any of our questions! We would surely return to this area and this house as we are neither fans of high rises nor crowded streets and restaurants. All the “locals” we met were very friendly and genuine—we had some great conversations with all of these folks. Be sure to feed the large tortoise which lives in Darlene’s yard and say hello to “Uno” the injured dolphin which lives in the marina at the end of the street. I could easily go on and on about this house and this area but you will have to discover all that on your own—safe travels!
Stayed 10 nights in Mar 2025
Verified

10/10 Excellent

Brian R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Darlene was an exceptional host and was very attentive to our needs. She communicates extremely well regarding and questions or concerns.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

craig g.

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

Amazing!

Best rental I've ever had!
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

Kati M.

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

Great Place to make memories

Second time staying here and we had a wonderful time! Will definitely stay again!
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Kat K.

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

A terrific place and location for fishing!

What a find! Highly recommend. Great location, very well-appointed, clean and comfortable place with everything you need. I planned this trip very last minute and Darlene was available immediately to answer several questions I had about bringing a boat. The place easily accommodated truck and trailer and another car. We also has access to her dock across the street at NO extra charge which was about as convenient as it gets to hop on and off easily. There is also a VERY nice boat ramp around the corner called Lavender’s Landing. You literally can not be in a better spot to reach great fishing. Boca Grande Pass, Captiva, Pine Island Sound, etc. Thank you Darlene, it was a wonderful stay. We will definitely return!!
Stayed 4 nights in Jun 2022

About the host

Hosted by Darlene Karl

Host profile image
Originally from Clarkston Michigan, I grew up enjoying the water where I once lived on a lake. Outdoor beauty is therapeutic for me as well and just important as indoor atmosphere. Light and cleanliness of an indoor space can bring me much satisfaction​. I hope if you choose to stay you will see the beauty not only inside but also outside with the landscaping and night lighting...

Why they chose this property

Many recent updates and attention to detail, however still leaving the character of an old Florida cottage. This cottage was once a home of fishermen who would come out for weekend fishing tournaments and such and then later owned by a famous musician. Come enjoy and see what brought them out years ago!

What makes this property unique

Upscale interior with old Florida look and comforts. High end a/c both quiet and includes heat. Location is unbelievable with just a monents walk to fresh seafood market and boat launch! Beautiful area to explore for kayakers fishermen or just plain beach goers, with Boca, Cayo, Capitva, Cabbage Key, Useppa and many more area just mins away by boat!

Languages:

English

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