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

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Another angle of the front
Little House lit up at night.
Another angle of Little House at night
Pathway from the patio to one of the bedrooms
The trees on the property are unusual Bonus to the guest who identifies them!

Reviews

8.8 out of 10
Excellent
5 bedrooms3 bathroomsSleeps 6278.7 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Rooms & beds

5 bedrooms (sleeps 6)

Bedroom 1

1 Double Bed

Bedroom 2

1 Double Bed

Bedroom 3

2 Single Beds

Bedroom 4

1 Single Bed

Bedroom 5

1 Single Bed

3 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub or shower · Toilet

Spaces

Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

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

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 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. New in 2021...Air conditioning in the guest house!

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 house 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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
There will be a fee added for pets
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Smoking

Smoking allowed: in designated areas
If coming from the beach please make sure you do not track sand in the house. Wash feet with hose at outside the front porch!
Thursday is trash day. Place garbage and recycling bins placed outside curbside Wednesday evening, as collection is early Thursday morning.

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 not indicated whether there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Boca Grande

Located near the beach, this cottage is in Downtown Boca Grande Historic District, a neighbourhood in Boca Grande. Whidden's Marina and ​Boca Grande Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Gasparilla Island State Park and Don Pedro Island State Park. Discover the area's water adventures with snorkelling, waterskiing and windsurfing nearby, or enjoy the great outdoors with cycling.
View more Cottages in Boca GrandeOpens in a new window
Map
Boca Grande, FL

Getting around

  • Punta Gorda Airport (PGD) - 54 min drive

Restaurants

  • ‪South Beach Bar And Grille - ‬4 min drive
  • ‪The Pink Elephant - ‬14 min walk
  • ‪Smokin Jerry’s - ‬13 min drive
  • ‪Miller's Dockside - ‬8 min walk
  • ‪The Outlet At The Inlett Restaurant - ‬18 min walk

Frequently asked questions

Is Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet. Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house?

As of 7 April 2026, prices found for a 1-night stay for 2 adults at Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house on 12 April 2026 start from NZ$1,599, 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.

How much is parking at Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house?

On-site parking is available at the property.

What time is check-in at Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house?

Check-in begins at 4:00 PM.

What time is check-out at Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house?

Checkout is at 11:00 AM.

Where is Delightful 'Old Florida' Island cottage in Boca Grande with separate guest house located?

Located in Downtown Boca Grande Historic District, this cottage is within a 5-minute walk of Boca Grande Historical Society and Museum, Our Lady of Mercy Catholic Church and Lighthouse United Methodist Church. St Andrews Episcopal Church and Whidden's Marina are also within 10 minutes.

Reviews

8.8

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 18 out of 28 reviews
Rating 8 - Good. 7 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 3 out of 28 reviews

9.2/10

Cleanliness

9.6/10

Check-in

9.4/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Christina C.

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

Boca grande fun

We enjoyed the proximity of this stay to all of the Boca grande spots. Jim was a great host and very easy to communicate with
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

Robert B.

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

Great location!

Two block walk to the beach, 5 minutes to main area of Boca Grande where all the restaurants and shops are, 10 minute walk/short golf cart trip to Millers. Worked great for our family and guests.
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Joanie P.

Comfortable and clean

Very charming and clean, happy house. Wonderful location! Owners very responsive to one question we had.
Stayed 9 nights in Dec 2018
Verified

10/10 Excellent

Kevan M.

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

Perfect getaway in Boca Grande

We loved our stay in the "Little House" in Boca Grande. The house is lovely - great decor, so many fun things to see all over this property. Plus we had everything we needed to cook with and so many fun dishes, glassware, etc. to use. The owner was very helpful and easy to reach. The location is perfect - 1.5 blocks to the beach and about 2 blocks to downtown. Can wait to stay there again!
Stayed 2 nights in Jun 2021
Verified

10/10 Excellent

Michael N.

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

Boca

Main house very nice
Stayed 3 nights in Jun 2023
Verified

8/10 Good

Verified traveller

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

Location Location Location

Very much enjoyed our stay. The location is perfect and within walking distance to the quaint town with restaurants, souvenir shopping, a little grocery store, an ice cream shop and more. Also, only a 2-3 minute walk to the beach. Please keep in mind the house is 100 yrs old but does have TV, WiFi, Washer/Dryer. AC and other modern appliances. All in all, a perfect fit for our family. Will stay again!
Stayed 5 nights in Jul 2022
Verified

10/10 Excellent

Octavia J.

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

Perfect old Florida Cottage

My family and I had the best time here over the holidays. The Hammonds cannot be a nicer host family. the day we arrived the heater in the back house was out and Peter helped find someone to come fix it on Christmas day! His help went far above and beyond!( The new bathroom renovation is lovely). Thank you, we look forward to returning often in the future. Please don't change a thing! Cheers, Octavia
Stayed 6 nights in Dec 2021
Verified

8/10 Good

Robert B.

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

Memorial Day in Boca Grande

We have stayed at this house before. The location is outstanding but if you have a boat, you will need to find another place to keep it, as this house is not on the water but it is a very short walk to beach. Also a very short walk to downtown Boca with many shops, restaurants, etc. There are two marinas close by, can walk but quick golf cart trip, but call way in advance to get a slip. There is little market on the island but would advise a stop at Publix just a few miles before you come over the bridge to the island to stock up on provisions. During warmer months, house definitely warms up despite AC running but it cools down after sun goes down and is very comfortable at night. AC mini splits in guest house rooms work great! Blinds on all the windows in main house would probably help this. Overall the house is a dated but the location is superb and we would definitely stay here again.
Stayed 3 nights in May 2024
Verified

2/10 Terrible

Leslie P.

Liked: Location
Disliked: Cleanliness, communication, listing accuracy

German Roach INFESTED property- Beware of Owner

*the house smells very badly *Very hot house that did not cool down. Air repair came twice and said it should cool down by the morning. Several floor fans but they only moved around the hot air and a few were broken *German roaches alive found on bed, bathroom, and kitchen floor *owner told me I could leave and he would give us a refund but there were no other properties available. When I asked to compromise and bring down the very hefty price for two nights down he called me names and threatened to call the Sherriff. *house was not cleaned properly and old food was left in kitchen *owner was extremely rude and said I was harassing him about the roaches and the air *Owner claims that I had 10 people with a reservation for 4 which I did not. I asked the owner if there was parking in advance of coming to Boca so that my adult children could come by and he said no problem there was plenty of parking * We saw 2 live cockroaches and several German Cockroaches which were running around the dishwasher and bed linens. I have photos and videos of everything. We were unable to leave since we had paid for a boating excursion all day Saturday and we couldn't recover our expenses. The owner says neighbors complained but that's impossible since we were gone the entire time except to sleep. We had 3 other families staying close by in different locations and we spent 90% of our time there. *the owner was responsive until he resorted to name calling, threats, and false allegations. He said I was harassing him but for what we paid I would expect much better. * We did have adult age children visiting other friends on the island and they stopped by which I asked about beforehand!
Stayed 2 nights in Jun 2022
Verified

8/10 Good

Bill L.

Liked: Cleanliness, communication, location, listing accuracy

Gasparilla Island Charm.

Great stay. Perfect location for walkable access to all of Gasparilla Islands laid back charm. Plenty of kitchen, living space and 2 comfortable BRs in main house. Guest house with 5 single beds in 3 rooms with one bathroom would probably work best for children. Initial hiccup on check in timing efficiently remedied by accessible and responsive owner.
Stayed 4 nights in May 2022
Verified

10/10 Excellent

Anthony T.

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

The perfect suite

This house fit our group perfectly. I would recommend.
Stayed 3 nights in Jun 2021
Verified

10/10 Excellent

Peyton P.

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

This is a great house in a fantastic location. We walked to beach, town, dinner, and boat docks.

Owner was great to work with and set the proper expectations beforehand. Highly recommend
Stayed 3 nights in Jun 2021
Verified

10/10 Excellent

Jo Ellen M.

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

Charming Vintage Home

Our small group stayed at this charming house during our tarpon fishing experience. The house is well stocked, perfectly located to town and beach and comfortable. It truly is vintage and reminded us of being at our grandparents' home - great memories. Our host Jim was easy to work with and answered our questions promptly. Hope to return in the future...
Stayed 2 nights in Apr 2021
Verified

8/10 Good

Erwin M.

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

Excellent location

Terrific location and responsive owners. A little dated but owner was upfront about that prior to booking. Bake setting on oven did not work but owner responded immediately regarding that. We really enjoyed our stay.
Stayed 7 nights in Mar 2021
Verified

10/10 Excellent

Henry T.

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

Boca Grande

Excellent unit. Would stay again next time I go if available
Stayed 2 nights in Sep 2020
Verified

8/10 Good

Gary D.

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

Great weekend

Close to beach and town great escape
Stayed 3 nights in Sep 2020
Verified

10/10 Excellent

sue d.

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

July 4th gathering

Enjoyed the historical feeling of the house, from the furniture to the pictures on the walls. Location was a short walk to the beach...we all had a great time!!!
Verified

10/10 Excellent

JR S.

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

Charming house

Clean classic bg look and feel. Courtyard was a beautiful surprise. Really enjoyed our stay.
Stayed 2 nights in May 2019
Verified

10/10 Excellent

margarita d.

Our stay at this lovely house was great. The house was just as we wanted clean, nice and confortable

The house is very well located, close to the beach and close to the town center and that is very helpful and nice. We had a wonderful time and hopefully we will come back soon to this lovely house. It has everything we needed in very good condition. The owner was very nice with us and I would love to tell him we had a very good time there and that the house is great. The location is great very close to other interesting towns and to nice shopping centers. We were able to walk, swim, eat at very good restaurants, we also went fishing and many other activities we like.
Stayed 14 nights in Jul 2016
Verified

8/10 Good

jill s.

Great location to town and beach.

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.
Stayed 10 nights in Dec 2017
Archival

10/10 Excellent

allison j.

Beyond exceptional - nowhere on Boca Grande we would rather stay.

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.
Stayed 1 night in Jun 2016
Archival

10/10 Excellent

Gian C.

Magical property

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.
Stayed 7 nights in Apr 2017
Archival

2/10 Terrible

Jennifer B.

It's a dump

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...
Stayed 3 nights in May 2017
Archival

10/10 Excellent

Leslie H.

Old-style Florida house in perfect location

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. Leslie
Archival

2/10 Terrible

Bayne S.

Cute, but overall very, very disappointing

The cottage was occupied by our guests, a group of Dartmouth College professionals. Their were numerous problems. First, The promised wifi did not work. Secondly, there was no television service. The shower did not drain properly and because of a lack of adequate hot water, all of our guests used the showers at the Gasparilla Beach Club. The house had a significant ant population. The back cottage was unusable; upon entry, we were greeted by three large Iguanas, between two and three feet long. No one dared stay in the "back" cottage. I rented additional rooms. There was an inadequate supply of linens; our guest purchased additional linens. The cottage was left in very good shape. The cleaning service of the owners claimed that it was a disaster and required 8 hours of cleaning. Of course, the owner is an absentee and refused to return the security deposit. I can verify all of the above statements. Bayne Stevenson

About the host

Hosted by James Hammond

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

Why they chose this property

Close to the beach close to town, close to the Boca Grande Community center....you 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 property 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...

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