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Pine Island Waterfront Condo in Tropical Paradise (506)

Bedrooms 2
Space 1,100 sq ft
Property type condo
Minimum Stay 3 - 30 nights


About the property

2 bedroom, 2 bath fully stocked condo with water views of marina and pool

Welcome to Southwest Florida's beautiful Pine Island, an 18 mile long tropical island paradise , where every morning is magnificent from the sunrises to the sunsets. Pine island has amazing waterfront, small town living, world class fishing and boating, lots of nature and wildlife, and is close proximity to the outer islands in the Gulf of Mexico (Caya Costa, Cabbage Key, Useppa Island and North Captiva).

The island is also tucked between Sanibel and Captiva islands, with Cape Coral on the mainland and the colorful, quaint fishing village of Matlacha at the entrance to the island. The Island has wonderful waterfront restaurants, art galleries and boutique gift shops, as well as a golf course and fantastic live entertainment by many local musicians. You can take fun filled day trips to Ft. Myers Beach and Naples as well.

Welcome to our lovely top floor unit at Four Winds Marina. This exclusive, gated, community has it all - comfort, views, pool, full service marina with boat docks, restaurant and fully stocked ships store.

Our unit (506) is a beautiful single level, top floor corner unit offering the finest in island getaway accommodations. It is a fabulous waterfront condo with a large wrap around, screened-in lanai (ceiling fan on lanai) including three sets of sliding glass doors throughout and cathedral ceilings. The Unit overlooks the marina, boat docks (separate rental through marina), and pool with fantastic views throughout. The unit is light and bright with morning sun and tastefully decorated with an island motive, including the owner's personal professional, nautical photography. It includes two bedrooms, two full bathrooms, and a fully equipped kitchen that provides abundant amenities to round out a relaxing boating / fishing vacation. Kitchen also equipped with a garbage disposal, ice maker and large pantry. The master suite has a king bed, big closet, double sinks and separate commode area with large tiled shower. Master also has a separate entrance to the lanai. Second bedroom includes twin beds (can pull together into a king bed) and full bathroom right outside in hall. There are large closets with plenty of storage.

The unit comes stocked with dishes, utensils, linens, including beach / pool towels and boating / fishing towels, pool noodles, blow dryer, and portable computer desk for your convenience. Enclosed parking for one vehicle, additional guest parking, and 6 X 6 locked storage closet is under the unit right next to the boat docks for you to store your boating / fishing gear. An electric grill, and four plastic chairs are available to barbecue your dinner right under the unit by the docks. The Four Winds complex also has a large, outside locked, heated non-chlorinated pool area with a changing bathroom just steps from unit. The pool area is very private surrounded by tropical foliage.

Four Winds Marina is a full service marina with boat facilities, gas, bait, fully stocked ships store and a wonderful restaurant (The Lazy Flamingo) – just walk your fillets in and they will prepare them to your taste and style for a nominal fee. Cayo Costa State Park, a short 20 minute boat ride across Charlotte Harbor, features 7 miles of pristine, sugar sand beaches. Water taxis are available. Boca Grande and other outer islands are just a boat ride away - The Tarpon Capital of the World. Fishing and kayaking also allowed off the seawall in the Four Winds complex.

Wi Fi, Cable TV (package includes Disney and CNN), and digital music included. TV's in living room and both bedrooms. Blue tooth player and weather radio included. Lots of DVDs, games, puzzles, binoculars, and more to make your stay enjoyable.

You'll love it.

More Details

Diane Gleason
Member since: 2015
Premier Partner

This partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks English
Response time:
Within an hour
Response rate:
Calendar last updated:
19 April, 2018

About Diane Gleason

Happily married to my husband, Tim, of 25 years. We read about Pine Island in the Florida Sportsman magazine in 2004, while living in San Diego, and came out for a vacation. We fell in love with everything about the island and bought a second home in 2005. We flew back and forth across country to visit four times a year for over ten years. After several years, we decided to retire here. Our dream finally came true and as of May, 2015, we live on Pine Island full time. We bought a unit at Four Winds when we got here in May, because over the years we enjoyed the marina so much, loved the private Four Winds Condo community, and wanted access to the fishing and outer islands at the north end of Pine Island. We also wanted a place to rent out to guests, have available for family to stay when visiting, and for Tim and I to use whenever it wasn't occupied.

I am active, adventurous woman who loves the outdoors and island lifestyle. My favorite activities are biking, kayaking, fishing, boating and swimming. I'm passionate about traveling all over the world and love to meet people from various places and to learn about diverse cultures. I enjoy eating local ethnic foods. My favorite countries are the Caribbean islands, Europe, Fiji, Bali, Thailand. And of course, my favorite place and home - Pine Island, FL.

Diane Gleason purchased this condo in 2015

Why Diane Gleason chose Four Winds Marina Condominiums

Incredible location, both the island and the rental unit. Fabulous fishing and natural setting with fantastic wildlife. Great water views. Your boat can be viewed from unit at all times since unit overlooks the marina and boat docks. Unit is top floor, large, bright and spacious with morning sunrises. Fully accessorized. Owner lives locally and is personally accessible during your stay.

What makes this condo unique

Pine Island is for the nature and wildlife lovers and avid boaters and fishing enthusiasts. To see PI is to fall in love with a place that is supremely it's own. Tim and I flew into Ft. Myers and then drove out to Pine Island in 2004 after reading about it in a magazine, and we knew we had to buy a condo right away and live here full time one day. Our 4 Winds unit is located in a full service marina with a fantastic restaurant and ships store. It's so close to incredible fishing and beaches and the people are wonderful. Out unit gets morning sun so window coverings can be open to the views all day without the arduous sun baking in. You can also see your boat from our unit if you rent a dock at Four Winds Marina. We know you'll love it here as much as we do.


Accommodation and facilities for this holiday condo in Four Winds Marina Condominiums in Bokeelia

Property Type:
  • condo
  • floor 2
Building Type:
  • building
  • Self-catering
Floor Area:
  • 1100 sq ft
House Rules:
  • Check-in: 15:00 / Check-out: 11:00
  • Max. occupancy: 4
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Water View
  • Waterfront
  • Away From It All
  • Family
  • Sports & Activities
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Hob
  • Toaster
  • Dining ...
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 - Toilet , Shower Enclosure , Large tiled shower with glass sliding door
    Bathroom 2 - Toilet , Bath with Shower , Tub and shower combination
  • 2 Bedrooms, Sleeps 4
  • Bedroom 2 - 2 Single Bed
    Bedroom 1 - 1 Extra Lg. Double Bed
  • Large closets Double Sink in Master Suite with separate commode area Remote Controlled Ceiling Fans
  • Books
  • DVD Player
  • Music Library
  • Satellite / Cable
  • Television
  • Video Library
  • Lanai / Gazebo ...
  • Barbecue
  • Long-term Renters Welcome
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool
  • Heated Pool
  • churches
  • festivals
  • Health/Beauty Spa
  • library
  • marina
  • restaurants
Leisure Activities:
  • beachcombing
  • bird watching
  • Boating
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • Shelling
  • sight seeing
  • walking
  • whale watching
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • jet skiing
  • Kayaking
  • pier fishing
  • sailing
  • snorkelling
  • bay fishing
  • surf fishing
  • swimming
  • tennis


Wonderful! 4.9/5 -
(10 traveller reviews)

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Pine Island Waterfront Condo in Tropical Paradise (506)
average rating of 4.9 based on 10 reviews

Perfect Vacation Get Away

  • 5 of 5

We had a wonderful time on Pine Island. The condo was beautifully decorated and so relaxing. Every morning we would have coffee on the waterfront balcony overlooking the marina. The owner provides you with information on dining, entertainment, fishing and golfing. We have never stayed at a place where there was such attention to detail! We have been to Pine Island several times and were happy to find a place at Four Winds Marina. We will definitely be going back for another stay!

  • Review Submitted: 22-Oct-2017
  • Date of Stay: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you ,Lisa. Lisa and her husband were the perfect guests. They were friendly, appreciative, and left my unit in perfect condition. Went over and beyond. I hope to see them again soon.
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Would Definitely Recommend!

  • 5 of 5

What a beautiful place to stay! The condo was amazing with all the comforts of home. We also loved that the island was so quiet. When we went other places, like Sanibel, the traffic was crazy but Pine Island is laid back. We would definitely book again!

  • Review Submitted: 01-Jan-2018
  • Date of Stay: December 2017
  • Source: VRBO, from HomeAway
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Bokeelia Vacation

  • 5 of 5

I wasn't able to make it to Bokeelia, Florida. I was admitted to the Eglin Hospital on the 17th September and I am still a patient in the hospital on 30 September 2017.

  • Review Submitted: 30-Sep-2017
  • Date of Stay: September 2017
  • Source: VRBO, from HomeAway
Owner's Response: I’m so sorry Jack and his lovely wife was not able to stay at my condo this time. I hope Jack is feeling better and they will be able to in the near future. I am happy to give him a 10 percent discount off the standard rates at that time. All the best. Diane
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Lake Wales, FL

Views you can not beat!

  • 5 of 5

We stay in Bokeelia every summer. This is our first time staying at Four Winds and the first time using Diane's condo! Everything about the condo was top notch! Diane met my 3 year old son and I, which she brought cookies for him that made his day, and went over many things in the condo! Which Im happy she did because if I came in on my own I would have many questions on what keys to use and so on. The condo has a wrap around porch so you can view the marina and the other side has a perfect view of the pool.

If you are bringing your own boat you do have to get a slip through the Marina and not with Diane. We were fortunate enough to get a slip right in front of our condo. If you are staying in Diane's condo, be sure to ask for slip 21!

I have nothing negative to say about Diane or the condo! Diane is so easy to work with and responds very quickly to any email/texts. I highly recommend this condo!

  • Review Submitted: 01-Jun-2017
  • Date of Stay: May 2017
  • Source: HomeAway
Owner's Response: Nicole and her family were a pleasure to host. They left my place immaculate and were gracious and friendly. I look forward to them returning in July and I hope they become regular guests to my rental.
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Beautiful Condo and Marina

  • 4 of 5

Our Stay over Christmas 2016 was wonderful and the weather was perfect.

The owner Diane met us at the Four Winds Condo to let us in, she went over everything in and out side the condo.

The stay was very comfortable and we would rent it again.

The Four Winds Marina has a boat rental available and we had a wonderful day on a 25' Grady White.

The Pool was very clean and the water was comfortable temp 85*. The surrounding landscape is beautiful ,very tropical. It's like going to the Keys but more peaceful. The Pink Flamingo is a good place to get something to eat and have a beer or glass of wine, located at the Four Winds Marina. Thanks Again Diane for letting our family stay in your Lovely Condo

  • Review Submitted: 09-Jan-2017
  • Date of Stay: December 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks Sonia. Would like to know what I could have done better in order to gain a 5 star? I've never gotten less than that before so it would be helpful to gain feedback on how to improve my renters experience. It was nice having a fellow CA on Pine Island. Hope you'll come again. Thanks, Diane
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Our incredibly magical stay in island Paradise, at the Four Winds Marina, Bokeelia, FL!!!!!

  • 5 of 5

My family and I had the best vacation, ever! The very clean condo was stocked with everything a person could want, need or think of… videos, puzzles… washer and dryer… action views, on-site boat rentals and a restaurant with $1.75 beers! There are 3 great restaurants, 2 marinas, golf course and convenient store, within a 2 mile radius of the condo.

We went by boat several times to a gorgeous 8 mile long beach, called Cayo Costa. It is a Federal Preserve. We went shelling and snorkeling. My EX(cellent) sister-in-law and sis found a humongous conch shell (it was dead, of course). It was 11” long and weighed approx. 3 lbs.! After a day at the secluded beach, we boated to 2 area restaurants. One was called the Bubble Room (awesome crab chowder and ambiance). The other was the unique Cabbage Key, on another Island. The entire ceiling was strewn with dollar bills signed by patrons, such as Clint Eastwood and Jimmy Buffet (locals say Buffet’s famous “Hamburger in Paradise” song was inspired by his visit to this eatery).

We also visited the Calusa Heritage Trail. It is only 2 miles from the condo. The Calusa Indian Cemetery and active archeological ‘dig” is sponsored by the University of Florida. The Calusa Indians lived on a nearby island, Useppa, before the 1st pyramid was ever built! When we were standing on a 20 foot high burial site, we were so engrossed in the readings about the Mound, we forgot to stand in silence, in memory of the thousands of Indians beneath our feet. The mounds were covered in conch shell, by the Indians. You can still see a few, on the surface. The Indians were driven off by the Spaniards and later absconded by the English, to be used as slaves. The most beautiful burial ground overlooks Pine Island Sound. You can make out fish houses way off in the distance, too.

Golfing was a must. The course fee was around $30. The place was a literal wildlife preserve. There are many Ibis, 6 types of herons, sandpipers, ahingas, cormorants, osprey nests and even an Eagle nest, too! The ponds are all inter-connected flowing with the tide in and out to Pine Island Sound. There are many fish and even crabs can be spotted. It also serves as a protective fishery for the baby fish, which abound, thus the heavy bird presence We also had a delicioso breakfast sandwich at the clubhouse. The have hot dogs and sausages, too.

This was the coolest vacation ever!

  • Review Submitted: 20-Nov-2016
  • Date of Stay: November 2016
  • Source: VRBO, from HomeAway
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Nearest Airport
40 Miles
Regional Southwest - RSW
Nearest Barpub
Lazy Flamingo
Nearest Ferry
Four Winds Marina
Nearest Golf
2 Miles
Alden Pines
Nearest Motorway
20 Miles
Nearest Restaurant
Lazy Flamingo
Nearest Beach
30 Miles
Sanibel Island
Car: recommended

Guide Fishing

Boat Rentals

Boating to Outer Islands

Shopping - art galleries and local gift shops

Great Restaurants



Prices & Availability

Prices for this holiday condo in Four Winds Marina Condominiums, Pine Island

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
May / June
1 May 2018 - 30 Jun 2018
4 night minimum stay
for 4 nights
1 Jul 2018 - 31 Jul 2018
3 night minimum stay
for 3 nights
Notes: Rates are based on 2 guests; add £8 per night, per additional guest
August / October
1 Aug 2018 - 31 Oct 2018
3 night minimum stay
for 3 nights
Notes: Rates are based on 2 guests; add £8 per night, per additional guest
November / December 2017
1 Nov 2018 - 31 Dec 2018
4 night minimum stay
for 4 nights
Notes: Rates are based on 2 guests; add £12 per night, per additional guest
2019 Season
1 Jan 2019 - 31 Mar 2019
30 night minimum stay
for 30 nights
My Standard Rate
3 night minimum stay
for 3 nights
Notes: Rates are based on 2 guests; add £8 per night, per additional guest

Additional pricing information

Additonal Guests Over 2 £7.1
Property Damage Protection £41.9
Cleaning £88.78
Tax Rate 11.0%

Rates are subject to change until reservation is confirmed.
Either $59 damage protection or $500 refundable security deposit (renter's choice)
Rates are based on double occupancy. Owner reserves the right to add up to $10 per night for each additional occupant.
Seasonal Rentals deposits are nonrefundable

Owner's Cancellation Policy

  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Owner a Question

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