Entire home

NEW!! The “WATERSIDE” COTTAGE~With dockage

Example of a golf cart to site-see or take you to dinner.

“Old Florida Cottage “ with modern WIFI and Cable TV! Just Remodeled!

Overview
Amenities
Policies
Location
Host

Exceptional

1 bedroom1 bathroomSleeps 2

Popular amenities

Parking available
Dryer
Pool
Washer
Barbecue grill
Outdoor space

Explore the area

Bokeelia, FL

Useppa Island
Cayo Costa Beaches
Useppa Museum
‪2 min drive‬
Fort Myers, FL (RSW-Southwest Florida Intl.)
‪69 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

MAIN

Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Separate dining area

Dining area

About this property

NEW!! The “WATERSIDE” COTTAGE~With dockage

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. You can catch Sheephead and Mangrove snapper right off the sea wall out behind this cottage. 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.

The golf carts/kayaks/boats/bikes are available to rent through a local resources! Golf cart approved areas make it a fun addition to the trip! Bike ride the entire island and stop for lunch or views! Kayaking this area is voted as one of the top spots and boating and fishing, what can I say.. both amazing off this island!

Wait till you see this freshly done cottage! Ready for your stay, bring your boat or rent one near by to dock here. Or, simply enjoy sitting by the water with a cup of coffee. New mini split a/c just installed to keep you comfortable on even the hottest of days! Lots of history on this beautiful island with fishing you'll be amazed with! Tarpon capital of the world and Charlotte Harbor moments away from the dock! Boca Grande, Cayo Costa, Useppa, North Captive, Sanibel and Cabbage Key, etc. a short boat ride away! The dock is a shared dock. Occasionally, I have guests from other cottages that may need dockage. These guests are asked to load and unload only.

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 properties:

The Lookout Cottage Property ID# 7371979 Bokeelia

The Quarterdeck Cottage Property ID# 4539791 Bokeelia

The Dockside Cottage Property ID# 9462163 St James City

Please check all four properties! All unique and beautifully decorated!

Property manager

Darlene Karl

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Kitchen

Washing machine

Dryer

Air conditioning

Outdoor space

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Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

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

On-site 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 that there is a smoke detector on the property

Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

A car is recommended for transport to and from this property

About the area

Bokeelia

Located in Bokeelia, this holiday home is on the waterfront. Boca Grande Lighthouse Museum and Whidden's Marina are local landmarks, and some of the area's activities can be experienced at Calusa Heritage Trail and Royal Tee Golf Club. Tropical Breeze Fun Park and Bowland Coral Lanes are also worth visiting. Discover the area's water adventures with scuba diving and snorkelling nearby, or enjoy the great outdoors with hiking and cycling.

Bokeelia, FL

What's nearby

Goodwins Island - 15 min walk - 1.3 km
Useppa Museum - 2 min drive - 1.7 km
Sun Splash Water Park - 34 min drive - 30.6 km

Getting around

Punta Gorda Airport (PGD) - 52 min drive

Restaurants

‪Lazy Flamingo 3 - ‬19 min walk
‪Tarpon Lodge - ‬7 min drive
‪Pine Island Pizza - ‬13 min drive
‪Olde Fish House Marina - ‬13 min drive
Cabbage Key Historic Inn & Restaurant

Frequently asked questions

Does NEW!! The “WATERSIDE” COTTAGE~With dockage have a pool?

Yes, this property has a pool.

How much does it cost to stay at NEW!! The “WATERSIDE” COTTAGE~With dockage?

As of 10 August 2025, prices found for a 1-night stay for 2 adults at NEW!! The “WATERSIDE” COTTAGE~With dockage on 11 August 2025 start from NZ$589.72, 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 NEW!! The “WATERSIDE” COTTAGE~With dockage pet-friendly?

No, pets are not allowed at this property.

What time is check-in at NEW!! The “WATERSIDE” COTTAGE~With dockage?

Check-in begins at 4:00 PM.

What time is check-out at NEW!! The “WATERSIDE” COTTAGE~With dockage?

Checkout is at 10:00 AM.

Where is NEW!! The “WATERSIDE” COTTAGE~With dockage located?

Situated on the waterfront, this holiday home is within 1 mile (2 km) of Goodwins Island and Useppa Museum. Calusa Heritage Trail and Randell Research 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

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Ron R.

20 March 2025

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

As Promised

My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly.

Stayed 3 nights in Mar 2025

10/10 Excellent

Wendy H.

16 March 2025

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

A lovely cottage

We enjoyed our stay very much. We knew the area very well and we're sorry to see that Captain Con restaurant had been destroyed by a hurricane. But enjoyed the Lazy Flamingo and loved Tarpon Lodge, as always. I went kayaking at Carmen's Kayaks. They were super helpful. Darlene, our host, was great. She was always available.

Stayed 3 nights in Mar 2025

10/10 Excellent

Jody R.

10 February 2025

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

Wonderful Stay!

We loved our stay here! Quaint, clean and a great location. Walking distance to Jug Creek Marina where there is live music until 8pm every day. There is also a bike path that runs the entire length of the island and easily accessible from the home. Check in was super simple and the host replied quickly to any questions and was very gracious. Fast access to the water if you have a boat. We will definitely be back!

Stayed 14 nights in Jan 2025

10/10 Excellent

Cheryl H.

16 March 2021

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

Dreamy Island Cottage

We had the best, relaxing time in this adorable waterside cottage. The host is the best!! We loved everything about this vacation spot.

Stayed 8 nights in Mar 2021

10/10 Excellent

Ramona "Sam" and Mike H.

9 November 2024

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

Coziest Little Cottage!!

My husband and I couldn’t have been more pleased with The Waterside Cottage! It exceeded our expectations and Darlene was the perfect host…made the entire process easy and was always responsive to questions, etc. The cottage was spotless and well stocked. We boated over from the East Coast of Florida and it was so condiment having the boat docked right out back. The cottage was so comfortable with such a great vibe we turned down dinner invites to grill and stay at the Cottage. We will definitely return!

Stayed 2 nights in Oct 2024

10/10 Excellent

Mike a.

9 August 2024

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

Mike and Val

Very nice

Stayed 2 nights in May 2024

10/10 Excellent

Terese P.

7 July 2019

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

Adorable cottage with great service!

The experience from booking to checking in was excellent! The owners responded to any questions immediately. The cottage itself is adorable and very clean. It really makes you feel at home. Location is good for things to do in both Bokeelia and Matlacha. Will definitely book this sweet cottage again!

Stayed 2 nights in Jul 2019

10/10 Excellent

Kierstan K.

16 August 2020

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

Cute cottage

Very impressed with this great little cottage. Extremely clean and prepped for any type of guest. Great backyard area with beach sand and water access, perfect to relax on the dock. Very responsive, kind property manager. Would definitely recommend!!

Stayed 2 nights in Aug 2020

10/10 Excellent

Chelsea H.

28 January 2021

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

Waterfront Bliss

We are return-renters of this host, and we cannot say enough good things about all of her properties that we have stayed in. We know the island well, and this little spot is a romantic getaway. We enjoyed our time on the back porch, over looking the water with a bottle of wine. 10/10 recommend!

Stayed 3 nights in Jan 2021

10/10 Excellent

Kelly D., naples fl

23 March 2022

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

weekend away

We had nice time in Bokeelia meeting up with some friends for a long weekend. The cottage is exactly as pictured. The kitchen was well stocked and we found we had everything we needed. The towels and linens were of nice quality which is appreciated. We had fun kayaking and fishing. My husband caught a few snapper right off the dock. The cafe lights out back made for a nice spot down by the water for a night cap.

Stayed 3 nights in Mar 2022

10/10 Excellent

Chris S.

21 April 2021

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

Wonderful Place to Recharge

Everything was wonderful. Space is bright and airy and very clean. Darlene was a joy to work with. She took care of everything. Perfectly. Would absolutely recommend this property for anyone wanting some peace and quiet to recharge their batteries. Would definitely stay here again. Thank you Darlene.

Stayed 4 nights in Apr 2021

10/10 Excellent

Lauren M.

14 April 2023

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

Special spot in secluded paradise!

This tiny house was exactly what my husband and I needed to celebrate a special anniversary. It’s rare for us to get a full weekend away, just the two of us, sans kiddos. We brought our 24 foot boat and had plenty of space to keep it at the dock and had ample space for our trailer. The neighborhood boat launch was also a major bonus. This sweet house is well-equipped and provides access to some of the state’s most beautiful beaches, perfect for island hopping and shelling. Thanks for the great stay and the wonderful memories!

Stayed 3 nights in Mar 2023

10/10 Excellent

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25 June 2021

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

The Waterside Cottage offers Old Florida feel with modern update and comfort.

This comfortable cottage is full of Old Florida charm. Perfect size for the two of us with all the kitchen necessities. Plus, nice linens, ample towels and great lighting throughout. Real comfy sofa too! We’ll definitely return with our boat when the weather is a little cooler so we can use the dock & backyard deck. Thank you again Darlene for answering all of our questions and being such a gracious hostess. PS - loved exploring the entire island - very unique - the rows of all the varieties of palm trees was amazing!

Stayed 2 nights in Jun 2021

10/10 Excellent

TomCheryl M., Bellingham, Washington

6 March 2022

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

Florida adventure 2022!

The Waterside Cottage and Pine Island is a Florida hidden gem! Upon entering the cottage we were in awe by all the thought put into the little touches to make this a destination memory. Waterside Cottage is even more beautiful than the pictures display. Darlene has done an excellent job of restoring and furnishing this vacation home. The cottage was well maintained and super clean. The living/dining area was tastefully and uniquely decorated. Well stocked kitchen with everything one would need. The bed was super comfy and the bathroom and shower were so unique. We loved the nickel flooring and lost count of how many nickels it took to complete that project! Watching the sunrise while enjoying our coffee on the back dock was a treat, especially when the resident manatee floated by. Wish we had morning doves in Washington, so peaceful to listen to. And those pelicans!! So fun to watch as they followed the fishing boats in the canal. The sunsets from the Bokeelia Pier were incredibly awesome! The pier is just a short venture from the cottage and worth the drive. Midnight star gazing from the dock is another plus! Exploring Pine Island was so peaceful. A very relaxing and laid back feeling. And oh my, Matlacha!! So fun!! Darlene was a delight to work with and an amazing host! A very kind and responsive owner. I only wish is that we could have stayed longer. Hopefully we can return again soon

Stayed 3 nights in Mar 2022

10/10 Excellent

Tessica E.

7 July 2025

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

Perfect!

Stayed 3 nights in Jul 2025

10/10 Excellent

Roger J.

29 January 2023

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

Amazing Cottage!

This awesome little cottage was wonderfully deceptive! It looks small as you pull up, but then you walk in to vaulted ceilings, and modern amenities - while still maintaining that gorgeous nautical feel! Little things like hidden ledge lighting, the bathroom floor's artistic and surprising material, and the gorgeous "propeller" ceiling fan, are just the cherry on top of such a wonderful, modern cottage! We loved it so much, my wife said on multiple occasions, said: "I'd live here!!!" Quick and thoroughly helpful communication with the proprieter, Darlene, helped make this brief get-a-way, way too short!!! #LovedThisPlace!!!

Stayed 1 night in Jan 2023

10/10 Excellent

Kimberly K.

18 August 2022

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

Quaint Cottage

The property was great! We enjoyed exploring other areas of Florida. Communication with the host was ver easy and responsive.

Stayed 3 nights in Aug 2022

10/10 Excellent

Terry G.

24 March 2022

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

Nested in on Pine Island

Quiet neighborhood, lovely home on a small island. Two small beach access points which is kept as a "secret". Nice place to escape to if you want to fish and not be around malls and franchise restaurants.

Stayed 2 nights in Mar 2022

10/10 Excellent

Stephen B., Bradenton, FL.

15 March 2022

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

Nice stay

Charming place

Stayed 2 nights in Mar 2022

10/10 Excellent

Phyllis F., Mobile, AL

15 March 2022

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

Cozy cottage

The waterside cottage is a jewel! It’s immaculately clean and superbly decorated. There’s a very nice boat launch a few blocks away, if you are a boater. You can also dock your boat in the backyard canal. We give this property an A+. I would highly recommend this property for a anyone wanting to get away and relax.

Stayed 3 nights in Mar 2022

10/10 Excellent

Terasa L.

16 January 2022

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

Absolutely Loved!!

Adorable cottage that is decorated so cute! Everything we needed included a boat slip and a very close boat ramp. Will definitely be back.

Stayed 3 nights in Jan 2022

10/10 Excellent

Jane W.

31 December 2021

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

Everything We Needed and More!

Darlene - highly responsive to all correspondence and requests. Savvy, loves her place in all the best ways. Cabin - pristine, bright, well-equipped (especially appreciated W/D unit, toaster, deck out back 10 steps from canal), calming, private. I slept on the sofa (2 nights) - admittedly a little bit of a trick since it's not a sofa-bed, but great recliner :) for an average-sized female. Surrounding area - perfectly quaint; great for folks seeking a glimpse into a bygone time. Loved kayaking (Carmen's Kayaks accommodated us on the fly and were sensitive to our unique needs); unbelievably good breakfast at Nick B's; WynDixie - impressive for such a small island; Learning about the Calusa (spelling?) Indians - humbling; Vietnamese restaurant in Matlacha - great take-out. We probably should have taken the ferry over to ritzy islands, but I couldn't make myself leave Pine Key. Maybe next time. December is a great time to visit this area. No bugs. No heat.

Stayed 2 nights in Dec 2021

10/10 Excellent

Gina B., Bradenton, USA

22 November 2021

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

Gorgeous Property!

This property was adorable! My husband and I had such a peaceful retreat! The cottage was impeccably clean, and Darlene, our hostess, was so easy to communicate with. We enjoyed sitting outside on the canal with our morning coffee, throwing a line in for Mangrove Snapper and Snook. The neighborhood was peaceful and quiet, but also close to anything you'd dream of doing. We were so grateful for such a restorative weekend here!! We can't wait to come back again!

Stayed 2 nights in Nov 2021

10/10 Excellent

Michelle X.

18 November 2021

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

Professional decorated with every amenity

Very clean and well appointed. The decor is next level. I’d stay there again.

Stayed 2 nights in Nov 2021

10/10 Excellent

Kurt O.

18 July 2021

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

Insta worthy cottage

Really cute Instagram worthy cottage. Authentic retro style meets cottage chic.

Stayed 2 nights in Jul 2021

About the host

Hosted by Darlene Karl

Thank you for your interest in my home. 7 years ago, I myself, vacationed here in Bokeelia, FL. I came here knowing that it was a beautiful barrier island, and to my amazement, it was SO much more. I couldn't believe the abundant wildlife, tranquil settings, nature trails and sights there are on this beautiful island. I came here for many of the same reasons you will be coming here for. The fishing, sun, boating, kayaking, nightlife, unique shopping (Downtown Matlacha) and some rest & relaxation. You will enjoy all of that and more, and I would be glad to be a part of making that possible....

Kind reqards,

Darlene

Why they chose this property

Cozy and cute, but most importantly clean. This romantic cottage will give you the full kitchen with setting areas outside to enjoy your coffee or watch your spouse clean his or her catch of the day. Old Florida life style is yours to enjoy!
I have several properties all located next to one another for family or friends to vacation together yet have their own space.
Other properties:
The Lookout Cottage Property ID# 7371979
The Quarterdeck Cottage Property ID# 4539791
The Dockside Cottage Property ID#
Please check all four properties! All unique and beautifully decorated!

What makes this property unique

Walk in shower, real nickel floors, vaulted ceilings with rope lighting for romantic lighting!

Languages:

English

Premier Host

They consistently provide great experiences for their guests

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NEW!! The “WATERSIDE” COTTAGE~With dockage

Photo gallery for NEW!! The “WATERSIDE” COTTAGE~With dockage

Reviews

Popular amenities

Explore the area

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 bathroom

MAIN

Spaces

About this property

NEW!! The “WATERSIDE” COTTAGE~With dockage

Property manager

Languages

Add dates for prices

Amenities

Have a question?

Similar properties

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

House Rules

Children

Events

Pets

Smoking

Important information

You need to know

We should mention

About the area

Bokeelia

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

10/10

10/10

10/10

10/10

10/10

10/10

10/10

Reviews

10/10 Excellent

Ron R.

As Promised

Ron R.

10/10 Excellent

Wendy H.

A lovely cottage

Wendy H.

10/10 Excellent

Jody R.

Wonderful Stay!

Jody R.

10/10 Excellent

Cheryl H.

Dreamy Island Cottage

Cheryl H.

10/10 Excellent

Ramona "Sam" and Mike H.

Coziest Little Cottage!!

Ramona "Sam" and Mike H.

10/10 Excellent

Mike a.

Mike and Val

Mike a.

10/10 Excellent

Terese P.

Adorable cottage with great service!

Terese P.

10/10 Excellent

Kierstan K.

Cute cottage

Kierstan K.

10/10 Excellent

Chelsea H.

Waterfront Bliss