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Private Tropical Pine Island Home!

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Last updated: 02/16/2017
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  • Minimum stay:7-10 nights
  • Sleeps:10
  • Bedrooms:5
  • Bathrooms:3
  • Property type:House
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:No

About the Property

Waterfront Luxury 5 bed/3 bath home -private pool, spa, gym & DOCK!

Upscale executive island style home with high end furnishings, a pool, spa and Private Dock! If a waterfront oasis on a quiet Tropical Island is what you are looking for, look no further!

It's one of the largest and more beautiful homes on the entire island. Great for extended family.

Note MONTHLY rates quoted are for 3 month stays or longer.

View of bay from Living Room & Kitchen's great room. In the backyard, this property features a large pool, hot tub, and a PRIVATE dock on a waterway which takes you to the best fishing, shelling and beach combing on the Gulf Coast. The lush, tropical landscape completes your retreat, adding privacy with the many Coconut Palms, Dates, Queens, Areca Palms and a wild Preserve Mangrove Forest bordering the property.

Trailer your boat down or rent one at the nearby marina and dock it behind the house. Behind the home is a 50 foot private dock for the larger yacht and a smaller dock and lift for small bow riders, flats boats or center consoles. Rent a kayak or have them delivered to the home to go explore the Mangrove jungle and back bays which are a little less than 15 minute’s paddle.

If you don't have a boat, you can fish (poles included) right off the dock or crab, or watch the dolphins and manatee that swim in for a visit. Read on for more features of this fantastic property!

The Grand Island Style 3 story Home lures you in with ceilings that soar 25 feet, wood floors and a spiral staircase up to the Skipper’s loft. Sleeps 10 comfortably without the need for sofa beds or futons with 5 bedrooms and 3 bathrooms.

1) Master Bedroom Suite (main floor)- King sleeps 2
2) Guest room 2 (main floor)- Queen sleeps 2
3) Guest room 3 (main floor)- Full sleeps 2 small adults
4) Guest room 4 (top floor loft) - Queen sleeps 2
5) Guest room 5 (bottom floor) - Murphy bed/Full sleeps 2 small adults

A Pak n Play is available in the home.

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. Slip into the Hot Tub after wearing 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 site-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 easy riding bike path that goes from our Southern part of the island all the way to the Northern end.

After a day out fishing, boating, basking in the sun by the pool or biking the bike paths on the island, it’s time to hang out on the dining deck overlooking the pool and waterway with an icy cold 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.

For dinner, 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 which seats 4 more.

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 25 foot ceilings, a 55' True LED Flat Screen SMART HDTV & Bose Surround entertainment system built into the 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 Wi-Fi in the home’s office in a cozy desk and chair.

Pine Island is on the Gulf of Mexico side of Florida, is the biggest and least developed Island on the Floridian Coastline. It's known for world class kayaking because of the many protected waterways, bays, and mangrove jungles that you can paddle through. It's also known for some of the best fishing in the state of Florida. 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 serve as protection from storms or the rare hurricane. The most pristine beaches in the country without the crowds are available to you and only close by- 'by boat'. You can either take a water (boat) taxi available from the island to the many outer islands, rent a boat at the nearby marina, or hire a private charter. Contact us for a list if you are the beach-goer type. We are NOT on the beach or near one unless you have a boat.

St James is the name of the sleepy fishing town on the very southern tip of Pine Island where this home is located and it's 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, a day spa, two gift shoppes, 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 more restaurants, 2 art galleries, a hardware store, a clothing store featuring resort style Florida women's clothing, 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, beautiful golf course 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 of your own to dock just behind the house. The nearest airport is RSW or Southwest International Airport which is about 50 minutes drive time from “The Island Retreat”.

We are a pet friendly property!
Send email


Member since: 2012

Speaks: english
Response time: Within 2 days
Response Rate: 90%
Calendar last updated: 02/16/2017

Property Type

  • House
  • 3880 sq. ft.

House Rules

  • Max. occupancy 10
  • Minimum Age Limit For Renters:

    Over 40...moreless

  • Children Welcome
  • Non Smoking Only
  • Pets Considered

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Long-Term Renters Welcome
  • Wheelchair Inaccessible

Bedrooms: 5 Bedrooms, Sleeps 10, Beds for 10

  • Bali Master Suite: 1 king


  • Ocean Blue Guest Room: 1 double


  • The Skipper's Loft Guest Room: 1 queen


  • Tropical Palm Guest Room: 1 queen


  • Budha's Rest Guest Bedroom: 1 double

    Pull down Murphy in the yoga area of the very large gym...moreless

  • All linens are included and made up before guest check in

Bathrooms: 3 Bathrooms

  • Main Floor Guest Bath: toilet, combination tub/shower

    Common area-main floor...moreless

  • Master Bath: toilet, shower

    In Suite-main floor...moreless

  • Pool Bath: toilet, shower

    bottom floor...moreless

  • Each bathroom is beautifully appointed with fresh towels and comes with check in amenities....moreless

Other Amenities

  • On the Water with Dock, Pool, Hot Tub, Wi-fi, Gym, Large Flat Screen TV with Bose Surround and whole house audio system. ...moreless


  • Books
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • Video Library


  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions


  • Bay/Sound
  • Botanical Garden
  • Churches
  • Cinemas
  • Festivals
  • Library
  • Live Theater
  • Marina
  • Museums
  • Playground
  • Recreation Center
  • Reefs
  • Restaurants
  • Ruins
  • Synagogues
  • Theme Parks
  • Water Parks

Local Services & Businesses

  • ATM/Bank
  • Babysitter
  • Fitness Center
  • Groceries
  • Hospital
  • Laundromat
  • Massage Therapist
  • Medical Services

Leisure Activities

  • Antiquing
  • Bird Watching
  • Eco Tourism
  • Paddle Boating
  • Photography
  • Scenic Drives
  • Sight Seeing
  • Walking

Location Type

  • Ocean View:

    Gulf of Mexico's intra coastal also known as San Carlos Bay...moreless

  • Rural:

    The least populated island off the coast of Florida....moreless

  • Water View:

    Views of water from back deck, side deck, backyard and sideyard. ...moreless

  • Waterfront:

    On water- dock and boat lift immediately behind the house and pool. Fish or take your boat to the beach or the 'fishingest' grounds in the country!...moreless

  • Waterfront:

    Waterway and canal behind home that you can boat or kayak into both a back back, intra coastal waterway to all the islands and the Gulf of Mexixo....moreless

Sports & Adventure Activities

  • Cycling
  • Deepsea Fishing
  • Fishing
  • Fly Fishing
  • Freshwater Fishing
  • Golf
  • Hiking
  • Jet Skiing
  • Pier Fishing
  • Roller Blading
  • Sailing
  • Scuba Diving Or Snorkeling
  • Skiing
  • Snorkeling
  • Sound/Bay Fishing
  • Surf Fishing
  • Swimming
  • Tennis
  • Water Skiing
  • Water Tubing
  • Wind-Surfing


  • Dining:

    6 at dining table, 4 on dining deck that adjoins and 63at breakfast bar that adjoins...moreless

  • Dining Area
  • Seating for 9 people


  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Fitness Room / Equipment
  • Garage
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine


  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster


  • Balcony
  • Bicycles
  • Deck / Patio
  • Lanai / Gazebo
  • Lawn / Garden
  • Outdoor Grill

Pool / Spa

  • Hot Tub
  • Private Pool


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Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Winter Season
Jan 2 - Apr 30, 2017
7 night min stay

$5,000 $10,000

Rates are based on 8 guests; add $25 per night, per additional guest

Nov 20 - Nov 27, 2017
7 night min stay

Christmas Break
Dec 22 - Jan 1, 2018
10 night min stay

My Standard Rate
7 night min stay

$4,000 $10,000

Rates are based on 6 guests; add $25 per night, per additional guest

* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates


  • Minimum Out Clean Fee $500
  • Pet Fee $250
  • Tax Rate 11%


-Please email to confirm your rate.

-The monthly rate shown is for seasonal stays only.

-Property has a 10 guest maximum.

-Pets are permitted with an additional $250 pet fee.

Owner's cancellation policy:

100% refund for cancellations more than 60 days before check-in date.

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Last updated: 02/16/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


  • Woody's Waterside

    "Full bar- outside by water and inside eating spaces. You can dock your boat and eat too!"

  • Ragged Ass Saloon

    "This is now called The Ragged Ass Saloon. Bar, eatery, waterfront dining, live entertainmen..."

  • Monroe Canal Marina

    "Boat Rentals, Kayak Rentals, Gas Dock, Bait Shop and Boat Ramp with lots of parking"

  • Kayak Voyagers

    "Enjoy the great blue way kayak trails around the islands. Pine Island's are not just open w..."

  • Tropic Star of Pine Island Inc

    "Dophin watching, Sunset Cruises and water taxi service to outer islands"

  • Alden Pines Country Club

    "Golf in Paradise!"

  • Giddyup Fishing Charters

  • Sun Splash Family Waterpark

  • Pine Island Flatwoods Preserve

    "Nature up close and personal"

  • Cape Coral Yacht & Racquet

    "Beach, Fishing Pier, Racquet Ball and Tennis Courts, Snack Bar, boat ramp"

  • Lakes Regional Park

    "Beaches, Mini Golf and many other family activities"

  • Shell Factory Nature Park

    "Oddities, amusements, bumper boats, gift shops, etc"

  • Broadway Palm Dinner Theatre

    "If you are in the mood for it is!"

  • Edison & Ford Winter Estates

    "Learn about the history of Thomas Edison and Henry Ford- neighboring estates, workshops, bot..."

  • Public Beach and Pier

    "The most crowded beach on the SW Coast is Ft Myers Beach. This is a spring break hang out. ..."

  • Lighthouse Park Beach Sanibel

    "Expensive- pay a $6 toll to get on this island, then pay $6 in parking to enjoy the Beach . ..."

  • Cayo Costa State Park

    "Best Secluded Beach in Southwest Florida. No way onto this island by by boat which keeps th..."

  • Sanibel Causeway

    "Skinny beach....but long.....must pay a 6 toll to get on causeway to park."

  • Lovegrove Gallery & Gardens

    "Gallery looks like the Wizard of Oz on the water. Paint a coconut to take home....she suppl..."

  • Four Mile Cove Ecological Preserve

    "Hiking & Trails- close to the heart of Cape Coral- but when you are in the preserve you'll f..."

  • Mike Greenwell's Family Fun Park

    "Arcade, Go Carts, Batting Cages, family amusement"

  • Randell Research Center

    "Indian Burial Mound, Park, Hiking Trail and archaelogical site"

  • Pine Island Paradise Paddling

    "Kayak The Blue Water WAY!"

  • Southwest Florida International Airport

    "New, clean airport"

  • Four Winds Marina

    "Boat Rentals & Water Taxis"

  • Big "M" Casino Cruise

    "Closest Gambling....while you enjoy a cruise. The ship departs from Estero Island which is..."

  • Murder Mystery Dinner Train

    "Enjoy a train ride, gourmet food and a show."

  • Cabbage Key Inn and Restaurant

    "Eat at this restaurant- can only get there by boat"

  • Barnacle Phils

    "Barnacle Phil's on Captiva Island- great place to visit and eat."

  • Kingfisher Aerial Sightseeing Tours

    "See ALL the islands by air tour!"

  • Red's Fresh Seafood House -- CLOSED

    "Huge Menu- Lots of delicious choices, the specials are great."

  • J. N. "Ding" Darling National Wildlife Refuge

    "You can see Alligators in the wild here and many, many, many bird species."

  • Cayo Costa State Park

    "Most Beautiful Beach in Southwest Florida. Take a water taxi or boat out to this pristine be..."

  • Belle's Secret Island Spa

    "Massages, manicures, pedicures, facials, & special island treatments."

42 Miles
Nearest Airport
Southwest Florida International Airport
0.5 Miles
Nearest Barpub
Low Key Tiki Bar & Woody's Waterside Cafe
12 Miles
Nearest Ferry
Water Taxi to outer islands- Tropic Star
13 Miles
Nearest Golf
Alden Pine Country Club
29 Miles
Nearest Train
Seminole Gulf Railway - Dinner Train
30 Miles
Nearest Motorway
Interstate 75
0.8 Miles
Nearest Restaurant
The Waterfront Restaurant & Marina
1600 Miles
Nearest Ski
Visit our Winter Retreat at VRBO 365599
3 Miles
Nearest Beach
Lighthouse Point Beach - by boat

Car: Recommended

a tropical island and Fisherman's paradise, without the high rise over development that most coastlines in the US have.

Pine Island's secluded and unspoiled location is home to exotic wildlife which can be seen in their natural habitat being most of this area and surrounding islands are protected preserves. Area waterways hold endangered manatees, bald eagles and dolphins. The waters are rich with marine life, among them tarpon, redfish, mullet, snook, and more.


-no traffic lights

- kayaking (rentals within walking distance)

-Belle's Island Day Spa within walking/biking distance.

- swimming in the pool or in the gulf

- boating (rent boats at nearby marina or bring yours & dock it behind the house)

- 8 miles of biking trails- (bikes on property or rent) at St Jude Harbour you can hike or bicycle through the woods and wetlands to the waters of Matlacha Pass over ground and over wood decking to see the native flora and fauna along this half-mile trail.

-visit the Calusa Indian Heritage Trail and Park, plus the Museum of the Islands

- fishing/crabbing & charters (deep sea or fly fish in the mangroves)

- there's an island golf course & tennis courts

- hike the many preserves on the island

-take a short ferry ride or water taxi to our barrier island Cayo Costa State Park with 9 miles of secluded beaches. It's not crowded because you can only get there by boat!

- scuba dive (dive boats go out from the many marinas on island)

- The Island Retreat is within walking distance (within a mile) to a bait & tackle shop, 5 restaurants, 3 bars, general store, marina, fish house, a day spa, a gift shop, and a playground/park.

- all within 8 miles by car- 12 restaurants, 8 art galleries, 3 gift shops, major super market.

- For you boaters, a gas dock is within a mile of the home or you can call Gulf Coast Fuel to fuel up you are 'The Island Retreat's' dock.

-For the kids, Sun Splash Family water park is 35 miles away.



Owner info

Year Purchased: 2001

About the owner: We come from the entertainment industry and still work in it full time. We are happy to share our Island Home with you.

Why the Owner Chose Saint James City, FL, USA:
We've always been attracted to quiet, unique, quaint and away from it all properties and environments that have a big emphasis on nature and adventure with little to no traffic or crowds and Pine Island definitely delivers big in that respect. Quiet, natural settings are very rare on Florida's coastlines. We are also avid Boaters and this island has the best access to at least 50 islands within 5-30 miles that you can get to only by boat, again leaving crowds way behind.

The Unique Benefits at this House:
This is NOT your standard, every day ordinary vacation rental. This is one of the most unique properties on the island with lots of entertaining space for family get-togethers. The olde Florida style architecture feels tropical, open and bright. The pool, hot tub, boat dock, tropical trees, widow's walk, gym, huge pantry space, and the fact that The Island Retreat is immediately across from a mangrove preserve that will never be built upon, along with it being on the most upscale street on the island as far as beauty of the homes really made it extremely desirable to us.

Contact us

Speaks: english
Response time: Within 2 days
Response Rate: 90%
Calendar last updated: 02/16/2017

Send email

Guestbook comments from the owner

1 of 1


  • Front of house

    Front of house

  • Pool & Spa combination with Teak Patio Dining and Umbrella

    Pool & Spa combination with Teak Patio Dining and Umbrella

  • Firepit


  • Private Gym-free weights, bench, treadmill, rack and flat screen TV.

    Private Gym-free weights, bench, treadmill, rack and flat screen TV.

  • Dining deck is great for breakfast out in the tropics. Also the BBQ deck.

    Dining deck is great for breakfast out in the tropics. Also the BBQ deck.

  • Office for checking email, surfing the net, & printing your boarding passes

    Office for checking email, surfing the net, & printing your boarding passes

  • Master Bedroom Suite.. Guest Bedroom 1 with ensuite beautiful bath

    Master Bedroom Suite.. Guest Bedroom 1 with ensuite beautiful bath

  • Huge Travertine Master Shower- gorgeous!

    Huge Travertine Master Shower- gorgeous!

  • Guest Room 2- Queen 'Skipper's Loft'

    Guest Room 2- Queen 'Skipper's Loft'

  • Skipper's Loft has it's own screened lanai & balcony

    Skipper's Loft has it's own screened lanai & balcony

  • Guest Room 3- Double with Walk in closet

    Guest Room 3- Double with Walk in closet

  • Guest Bedroom 5 with Double on bottom floor adjacent to Pool Bath

    Guest Bedroom 5 with Double on bottom floor adjacent to Pool Bath

  • View from Living Room and Living room Balcony

    View from Living Room and Living room Balcony

  • Docks and Boat lift- there is also a longer third dock not pictured

    Docks and Boat lift- there is also a longer third dock not pictured

  • Private pool big enough for swimming laps!

    Private pool big enough for swimming laps!

  • Jump in the Hot tub after working out in your private gym.

    Jump in the Hot tub after working out in your private gym.

  • Fireplace for chilly nights or just atmosphere.

    Fireplace for chilly nights or just atmosphere.

  • Kitchen is open to dining, living and deck area.

    Kitchen is open to dining, living and deck area.

  • Master has it's own balcony with water views and walk in closet

    Master has it's own balcony with water views and walk in closet

  • Master Bath is 'in' suite with lighted make up vanity & dual pedestal sinks

    Master Bath is 'in' suite with lighted make up vanity & dual pedestal sinks

  • Skipper's Loft....Guest Bedroom 2....

    Skipper's Loft....Guest Bedroom 2....

  • Guest Bedroom 3- Queen

    Guest Bedroom 3- Queen

  • Full Bath on Main Floor

    Full Bath on Main Floor

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Minimum stay 7-10 nights
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