Bay View from Living Room and Living Room BalconyFront of Home

Entire home/apt

10 Guests

5 Bedrooms

5 Beds

Entire home/apt

10 Guests

5 Bedrooms

5 Beds

Please set the number of adults.
Please set the number of children.
Ages 2 - 12
Please set the number of infants.
Under 2
10 guests maximum. Infants don’t count toward the number of guests.
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About this listing

A Waterfront, Executive Island Style Home with 5 bedrooms and 3 bathrooms, Private Pool, Spa, Gym, Study and Dock!

Get ready for a boating and fishing paradise with water access from the backyard from your very own private dock.

The space

A waterfront oasis with private pool, spa, gym and dock! Escape the Typical!

One of the few upscale executive tropical style homes on the island. The Island Retreat is located on a private road with Coastal views and backed up to a waterfront waterway which takes you to the best fishing, shelling and beach combing on the Gulf Coast. A tropical landscape completes your retreat, adding privacy with the many Coconut Palms, Dates, Queen, Areca Palms and a wild Preserve Mangrove Forest to the front side and a smaller one on a quarter of the back side of the property. If a more private waterfront setting is what you seek, the landscape provides this for you.

Trailer your boat down to “Your Island Retreat” or rent one at the nearby marina and dock it behind the house. Behind the home are two private docks, 1 is a 50 foot dock for the larger yacht and a smaller dock and boat lift for small bow riders or center consoles. Or rent a kayak to go explore the Mangrove jungle and back bays which are a little less than 15 minute’s paddle from The Island Retreat.

Not a boater? You can fish (poles included) right off the dock or crab, or watch the dolphins and manatee that often swim in for a visit. Another enticing natural feature of The Island Retreat is the Sea Hawks. Watch these birds of prey fish for their young, observe the lazy Pelican’s crash dive into the water for a fish or two from their perch on the dock’s pilings, or, you could lounge lazily in the shade in the fenced in area which is a great outdoor space for your pets or the kids to play in the shells.

This grand Island Style 3 story Home lures you in with soaring ceilings and wood floors and a spiral staircase up to the Skipper’s loft. With 5 bedrooms and 3 baths, this 5000 square foot Island Retreat Vacation Home sleeps 10 very comfortably without the use of sofa beds or futons.

Master Bedroom Suite- King Sleeps 2
Guestroom 1 (Tropical Green)- King Sleeps 2
Guestroom 2 (Ocean Blue)- Queen Sleeps 2
Guestroom 3 (Skipper's Loft) - Queen Sleeps 2
Guestroom 4 (Buddha's rest) - Murphy bed/Queen Sleeps 2

Take a dip in the large heated pool or sun yourself on the pool deck where you can relax or watch the big game or favorite show from the pool. The pool deck is outfitted with two outdoor flat screen TVs! A dining table and umbrella on the pool deck await you for lunch. There’s also a Hot Tub if you wore yourself out in the fully outfitted Gym with a nice sized selection of free weights, a weight machine and treadmill with flat screen TV and a meditation area for Yoga. If you'd rather sight see while exercising, grab one of the Island Retreat's bicycles for an exhilarating ride all the way to the other the end of the island and back. There is a flat bike path that goes from our Southern part of the island all the way to the Northern end. 16 miles of bike path round trip for your riding pleasure!

After fishing, boating, basking in the sun by the pool or biking the paths on the island, it’s time to relax out on the dining deck overlooking the pool and the water with a cool drink and enjoy the sunset, or for a higher up view, go all the way up to the top deck patio off the Skipper’s Loft.

When it’s time for dinner, you can expect an accommodating kitchen with everything you need to create a gourmet meal. There’s a breakfast bar which seats 3, dining room area open to the kitchen which seats 6 and the dining deck outside and under cover is also adjacent to the kitchen and seats 4 more, comfortably seating 10-13.

After dinner, enjoy a port wine or coffee in front of the fire place or move to the living area open to the kitchen and two decks with 30 foot ceilings, a 55" LED Flat Screen TV with Smart Technology & Bose entertainment system built into wall. Audio speakers are throughout the home, gym and pool deck linking to the home's entertainment system. Or feel free to check your email or surf the net with free Wifi in the home’s office in a cozy desk and chair.

About “The Island Retreat’s” location- Pine Island, on the Gulf of Mexico side of Florida, is the biggest and least developed Island on the Floridian Coastline. The nearest metro area is 20-30 miles away on the mainland which is the Cape Coral/Ft Myers area. Pine Island enjoys Sanibel and Captiva as barrier islands which serves as protection from storms or the rare (website hidden) James is the name of the sleepy fishing town on the very southern tip of Pine Island where “The Island Retreat” is located and is immediately off the Southwest Coast of Florida and connected by bridge through Matlacha (pronounced: mat-lah-SHAY) to Cape Coral. Though sleepy and quaint, St James features 4 restaurants, 2 bars, a marina, a general store, and a fish house with fresh fish, shrimp, clams and crab brought in daily wholesale all within a short walk or bike ride. An 8 minute drive will bring you to the middle of the island (which the locals call “the center”), where there is a major grocery store, liquor store, 3 restaurants, hardware store, gas station, pizza place and Subway sandwich shop. A further 10 minute drive and a right at the center onto “little Pine Island” will take you to Matlacha, which features up to 18 different art galleries all in a row, a coffee shop, 4 restaurants, and other gift shops that are worth a visit. If you visit the Northern part of the island called Bokeelia, you can expect more restaurants, art galleries and a historic Indian burial mound and park, along with water taxi service to the outer islands if you don’t rent a boat or trailer your own boat to the dock just behind the house. There is a marina with a boat ramp 3 minutes from the retreat to get your boat in the water, then you can navigate around to dock it behind The Island Retreat. There is a 10,000 boat lift next to a 50 foot dock behind the home.

The nearest airport is RSW or Southwest International Airport which is about 45 minutes away from “The Island Retreat”.

A pet friendly property.

Guest access

The whole home and garden is private, so the pool, gym, spa and dock are for only you and your family to enjoy. Guests have access to the Gulf of Mexico through a waterway that is directly behind the home. There's a public park playground for the kids just a block away. Also, a Fish monger 2 blocks away. Bars, restaurants, general store, bait shop, and marina all within a half mile from the home.

Interaction with guests

We maintain contact from reservation creation to check in via email. While on property, property manager available to you by phone.

Other things to note

A specific Island Retreat vacation rental agreement is required to be signed to confirm your booking for this property.

The space
Bathrooms: 3
Bedrooms: 5
Beds: 5
Check In: 3PM - 8PM
Check Out: 10AM
Room type: Entire home/apt


Extra people: $50 / night after 8 guests
Cleaning Fee: $385
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House Rules
No smoking
Check in time is 3PM - 8PM

House rules and Manual is on the coffee table and is a party to your agreement.

-No Smoking inside the Home.
-Children who cannot swim or are under the age of 10 are not allowed on the pool deck or on the upper Skipper's Deck without adult supervision.
-Pets must relieve themselves in the gated play yard. Please be sure you pick up after your pets on the Island Retreat's Grounds.
-If using any of the homes tools in the garage, fishing gear, bikes etc, make absolutely sure they are put exactly where you found them. If we can't find them on check out, your deposit will be debited.
-Use only the towels designated for boating and fishing (in the downstairs pantry). House towels which are in the bathrooms are not permitted off the property or may be used for cleaning up spills or for fishing & boating. The towels in the downstairs pantry are clean but already stained or bleached. USE THESE TOWELS for anything other than drying yourself off.
-Garbage day is Tuesday. Although there are many big cans in the garage please put them curbside early Tuesday morning. You don't want a stinky house!
-Boat trailer cannot be parked in driveway or the HOA will fine you. It must either be parked in the garage or be parked behind the fence all the way behind the property.



Cancel up to 7 days before your trip and get a 50% refund plus service fees back.

Safety features
First aid kit
Smoke detector
Fire extinguisher

10 nights minimum stay.
From May 1 - Nov 18, 2017 the minimum stay is 7 nights.

4 Reviews

Check In
Trista User Profile
February 2016
Amazing place, just what we were looking for. Highly recommend it.

Mary User Profile
August 2015
Yes, Kevin was very gracious! At first I thought "wow, we are so far from everything" but actually it was a blessing, we enjoyed the pool and boating (a boat is a must) every was so relaxing!! The house is beautiful and comfortable, it had everything we needed. We watched the sunset and dolphins every night by boat out by the mangroves, so awesome.

Peter User Profile
January 2014
We spent a week @ Island Retreat over NY's and the house was exactly what we had hoped for - well furnished, clean spacious and ideal for our extended family. Appreciated the info left regarding things to do in the area - John, who came to houe to orientate us to the home was very accomadating.

Suzanne User Profile
February 2013
The Island Retreat is absolutely lovely, with lush tropical landscaping and a spacious, beautifully appointed home featuring art and artifacts from around the world. It really feels like home, restful, lovely and inviting. We enjoyed the quiet, all the different decks and balconies, the grill (used for delicious grouper, crab claws and shrimp) after a visit to the fishmonger, just a few short blocks away. The bikes were great, the spa and pool a daily favorite, although we would have liked the pool to be warmer. Island can't beat it!

This host has 24 reviews for other properties.

View other reviews

Florida, United States · Joined in October 2011
Kevin User ProfileKevin is a superhost.

We are meticulous about our properties. Every detail is kept just how we'd want it if we were on vacation. My wife goes OCD on the details, so if you find something that may be missing we'd be thrilled to hear about it during or after your stay.

Both my wife and I are in the entertainment business and have chosen properties that are quiet, secluded and absolutely gorgeous to retreat away to.

Response rate: 100%
(last 10 contacts)
Response time: within a day
Exact location information is provided after a booking is confirmed.