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Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house

Bedrooms 5
Space 3,000 sq ft
Property type cottage
Minimum Stay 1 - 3 nights
Popular Features
  • Fireplace
  • Barbecue
  • Washing Machine
  • Air Conditioning
  • Internet
  • Parking


About the property

5 bedroom 3 bath house and guest quarters in Boca Grande Historic District.

Available for short or seasonal rental is Little House: a traditional 'Old Florida' cottage with separate guest house set in the historic district of Boca Grande, on Gasparilla Island (Florida Gulf Coast). Great beaches are practically a stone's throw away. (Walk to the beach in under 2 minutes...walk in fact to anything you want in town in 5minutes.) There's no fast food, no chain stores, just a unique and charming slice of bygone Florida ; Florida as it was meant to be, to borrow a tagline from the Gasparilla Inn. Available weekly or monthly. Convenient to golf. This charming property, which has everything you need and nothing you don't consists of two buildings as below:

Main house: master bedroom has (1) queen bed & attached bath; guest bedroom has (1) King bed attached bathroom; living room/dining room; large screened porch with dining table & sitting area (and glass sliding windows if it gets cold); lovely private outdoor courtyard with chairs for dining & relaxing; sunny eat-in kitchen -- easily seats (6); pantry; den with cable TV/DVD; washer & dryer; dishwasher & garbage disposal; grill; central a/c; telephone with answering machine. WIFI of course

Separate guest house (perfect for older children) laid out as follows:

a guest bedroom with (2) twin beds, a second guest bedroom with (2) twin beds, and a third guest bedroom with (1) twin bed. There is one bathroom for all three bedrooms. (Please note, the guest house has no AC.)

A shed contains a 6 bikes available to renters, plus the charcoal grill, etc.

About Boca Grande: Boca Grande is a charming village on 7-mile-long Gasparilla Island, located between Fort Myers and Sarasota. Access to Boca Grande is via a toll bridge which keeps the Island peaceful and quiet. Legend has it that the infamous pirate Jose Gaspar once lived here in grand style. Later discoverers in the early 20th century included Boston Brahmins and other elites from the North-east, who made it a winter playground for some of the nation's most prominent families and their guests. The lure then, as it is now, was the wonderful weather and some of the world's best tarpon fishing. Boca Grande retains unusual character. Its old Florida architecture, and its small town feel (devoid of big box retailers, chain stores, etc.), make it a destination for discerning vacationers. Visitors to Boca Grande enjoy miles of beaches on the island, picnicking, fishing, swimming, shelling and boating, as well as tennis and golf.

Little House was built early in the 20th century as housing for executives of the railroad. It has been in our family continuously since the 1920s.

Note: This is as traditional a ouse as it gets in Boca Grande, in the best part of town. Close enough to everything you want in the village, yet just far enough way to be quiet and restful.

More Details

James Hammond
Member since: 2007
Speaks English, French, Spanish
Response time:
Within 12 hours
Response rate:
Calendar last updated:
18 June, 2018

About James Hammond

We live in the Boston area, and I have been going to Boca Grande since I was a child.

James Hammond purchased this cottage in 1921

Why James Hammond chose Boca Grande

Close to the beach close to town, close to the Boca Grande Community can arrive and never get behind the wheel of a car. The Community Center, where lectures, movies and other notable happenings occur, is just across the street. The village a couple of blocks through the most charming part of Boca Grande. Arguably the best beaches on the island are just a few paces away. You will love the patio complete with its wrought iron gates, brought (it is said) from Cuba by one of Teddy Roosevelt's Rough Riders.

The guest house let's you put the next generation or your guests in their own space. In the shed find you'll find bikes beach chairs, umbrellas etc., all for your use.

What makes this cottage unique

A word of warning. Do not come here if you are looking for large marble bath and Jacuzzis. This is Old Florida not Vero Beach. They did not have those things in the 1920s and we don't have them in Little House now. There are plenty of condos on the island for that sort of thing. Come here if you want to go back to a simpler more relaxed era, and ease into a bit of Florida you never imagined still existed...

Guestbook comments from the owner

We love this island and this house....a blissful week in a very special place.

Amy Woodcox
Nov 2007
  • 1 of 1


Accommodation and facilities for this holiday cottage in the Boca Grande in the Lee County

Property Type:
  • cottage (detached)
  • Self-catering
Floor Area:
  • 3000 sq ft
House Rules:
  • Max. occupancy: 9
  • pets considered
  • children welcome
Location Type:
  • beach
  • near the sea
  • town
  • village
  • Family
  • Sports & Activities
  • Air Conditioning
  • Broadband Access ...
  • Fireplace
  • Garage
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Parking
  • Telephone ...
  • Towels Provided
  • Tumble Dryer
  • Washing Machine
  • 4 Ring Stove
  • Coffee Maker ...
  • Dishwasher
  • Freezer ...
  • Grill
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Toaster
  • Dining Area
  • seating for 6 people
  • 3 Bathrooms
  • Bathroom 1 - Toilet , Shower Enclosure , En suite with bedroom
    Bathroom 2 - Toilet , Bath with Shower , En suite with bedroom
    Bathroom 3 - Toilet , Bath with Shower , Shared with 3 bedrooms in dependency
  • 5 Bedrooms, Sleeps 9
  • Bedroom 3 - 2 Single Bed , Detached dependency
    Bedroom 4 - 1 Double Bed , Detached dependency
    Bedroom 5 - 1 Single Bed , Detached dependency
    Bedroom 2 - 1 Large Double Bed
    Bedroom 1 - 1 Large Double Bed
  • In the main house, one bedroom with full-size bed has a door to the backyard and en suite bath; the other bedroom has a queen bed and en suite bath. In the detached dependency, there are three bedrooms with one bathroom. This is a great place to put guests, or older kids, as they'll have the option of staying out of your way.
  • Books ...
  • DVD Player
  • Satellite / Cable
  • Television
  • Video Library ...
  • Balcony
  • Bicycles ...
  • Boat ...
  • Golf ...
  • Garden ...
  • Barbecue
  • Tennis ...
  • Terrace
  • 4 bicycles
  • 6 garden chairs
  • Long-term Renters Welcome
  • suitable for elderly or infirm
  • wheelchair inaccessible
  • botanical garden
  • churches
  • library
  • marina
  • recreation centre
  • restaurants
Leisure Activities:
  • beachcombing
  • bird watching
  • paddle boating
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • pier fishing
  • roller blading
  • sailing
  • snorkelling
  • bay fishing
  • surf fishing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Public tennis courts are in 3 minutes walking distance, and the ocean is 2 blocks away. Cottage and guest house cannot be rented separately.


Good! 3.9/5 -
(9 traveller reviews)

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22% Complete
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Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house
average rating of 3.8888888 based on 10 reviews

Great location to town and beach.

  • 4 of 5

We had a lovely time at this quaint little cottage. It’s location is perfect for walking into town and to the beach. It was clean with a washer and dryer. If you enjoy older homes with historic value, this is the place for you. The front porch was a morning favorite to enjoy our coffee and tea. I highly recommend this property. Owners very connected and easily accessible. They were very attentive.

  • Review Submitted: 05-Jan-2018
  • Date of Stay: December 2017
  • Source: HomeAway
Owner's Response: I am so glad you all came and stayed in our house, and got a chance to enjoy Boca Gande. Thank you for being such excellent guests. You will always be welcome at Little House...thanks again!
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Beyond exceptional - nowhere on Boca Grande we would rather stay.

  • 5 of 5

You don't have to be a sucker for historic cottages to love this property because the comforts of modern day living surround you in every ;picture perfect room. I want to take the time to review this home because of how grateful we are for the experience of a home that required the kind of care the owner took to love and preserve the most important elements of Florida's past. Our grown sons immediately took to the lovely sleeping porch replete with rocking chairs and a large dining table for their post fishing cocktail hour. The beautifully appointed rooms are separated by a charming butlers pantry, a long living room with nooks and cozy reading areas initiating privacy at every turn. Two bedrooms in the main house are sizable with comfy queen size beds and each have their own updated bathrooms (The linens are lovely, the towels are luxurious). A separate room that serves as a den is another private setting with a tv. The kitchen is a well stocked eat-in affair that was updated just enough to leave you with a little sense of how we once lived.

The outdoor areas conjure up images of gracious soirees- porches and porticos, glorious ancient fruit trees and a preserved remade servants quarters that serves as a guest house.

We want to thank the owners again for their attentiveness to all our needs as guests and as stewards of home for the ages.

  • Review Submitted: 30-Sep-2017
  • Date of Stay: June 2016
  • Source: VRBO, from HomeAway
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1 0

Magical property

  • 5 of 5

This was the second time that we stayed in this house and on this property. Generic it is not. It always feels like we are in Rome when we stay here and the location can't be beat. The inside of the house is charming and the gardens are very old school. This is a true southern property with all the charm and history. It's right in town so you can walk or ride your bike to a late dinner and then ice cream with the kids. Everyone can run back and forth to the beach which is spectacular. If you are looking for a managed property with generic tile floor and a balcony with stain-proof flowered furniture and a community pool then this isn't the place for you. But if you want a unique experience that feels like Nantucket moved to the south then there isn't much like it.

  • Review Submitted: 26-Sep-2017
  • Date of Stay: April 2017
  • Source: HomeAway
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It's a dump

  • 1 of 5

This place is a dump... pictures are outdated and the furniture and rugs are all filled with stains and the guest house.... I have no words to describe...

  • Review Submitted: 01-Jun-2017
  • Date of Stay: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: A dump? Gee, thanks. Tell us how you really feel.... In fairness, we should not have rented to the reviewer, not then. The house was in the middle of significant capital projects (rebuilding the original wooden windows, installation of a new roof on the guest house, painting of the exterior and the porch.) It clearly was not clean enough, and yes, the carpets, subjected to the heavy heals of workmen, will have to be replaced. That said, there was full disclosure and the rate was reduced (we assented to less than the minimum stay as there was not availability on the island, the renter having booked all the rooms at the Inn.) The renter was fully refunded, including the ordinarily non- refundable deposit. The house will have updated furniture for the Autumn. As work is finished, we will update photographs.
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7 0

Old-style Florida house in perfect location

  • 5 of 5

Our annual stay at Little House in March is what gets me through the New England winter. It is a charming, easy, authentic old Florida house that is perfectly located in the historic district. Within a couples minutes walk you can either be at the beach or in the quaint village. Now that I am back in the gray of the north and a spring that doesn’t want to arrive, I am missing our bike rides around the island, the wonderful shelling and walks on the beach and swimming, and my all-time favorite reading spots on the sunny porch or the very private patio on a chaise longue. The house is very comfortable and well equipped, and you will want to keep coming back.


  • Review Submitted: 06-Apr-2017
  • Date of Stay: March 2017
  • Source: HomeAway
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  • 5 of 5

Grand View Cottage is beautiful in ways that we don't often have an opportunity to experience unless you remember the Florida we all loved as children. The home is beautifully appointed and tastefully updated in a warm and welcoming style. The two ensuite baths are lovely, the views to the garden and the grounds from most rooms of the house are peaceful and pretty. It is stocked for culinary excellence or boiling up the shrimp we picked up at the dock as the boat arrived at the end of the block. The owners are delightful and accommodating. We would love to call this our true home.

  • Review Submitted: 12-Dec-2016
  • Date of Stay: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: I am so glad you had a good stay and hope you come back again. (We call it Little House though!) Thanks for taking such good care of our property, you were dream visitors.
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Nearest Airport
54 Miles
Ft Myers
Nearest Train
54 Miles
Ft. Myers
Nearest Motorway
20 Miles
Intestate 75
Nearest Beach
100 Metres
Gasparilla Beaches
Car: recommended

Gasparilla Island is famous for tarpon fishing. The town of Boca Grande itself is a jewel of off the beaten track and preserved piece of old Florida. Bicycle, run, walk or roller blade past cottages like ours, or the houses of fabled American families, who have made this island a special place since the early 20th century. Use Boca Grande as a base to explore Sarasota where the Ringling Museum affords an excellent outing, or Ft. Myers, where the house of Thomas Edison preserves his laboratory (and is sited right next to Henry Ford's!) If you feel you must, Disney World is in striking distance, if you don't mind driving for a couple of hours each way.

Gasparilla Island caters to a well heeled but discrete clientele...a bit of an antidote to the East Coast's resorts. It's more Old Yankee than flashy New York. You'll be amazed a place like this still exists.


Prices & Availability

Prices for this holiday cottage in the Boca Grande, Florida

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Off Season
1 Apr 2018 - 31 Oct 2018
Changeover Day: Saturday
1 night minimum stay
for 1 night
Notes: Rates are based on 5 guests; add £81 per night, per additional guest
2019 Season
1 Nov 2018 - 31 May 2019
Changeover Day: Saturday
3 night minimum stay
for 3 nights
Notes: Rates are based on 5 guests; add £81 per night, per additional guest

Additional pricing information

Cleaning Fee £225.87
Pet Fee £225.87 + Tax
Refundable Damage Deposit £376.45
Stay tax 7.0% per night. This amount will be due to the owner upon arrival.

Please inquire directly with the owner for longer term rental rates.

Additional security deposit required: 500USD for weekly rentals, 1500USD for monthly rentals. Any term over one week will include an additional 500 USD fee for maid service per week period. Pets are permitted. (An additional fee may apply on a discretionary basis depending on the kind of pet.)
No smoking allowed inside the house.
Cottage and guest house cannot be rented separately.

Owner's Cancellation Policy

100% refund for cancellations more than 90 days before check-in date.
Ask Owner a Question