Hemingway Cottage Sunsets Await Your Arrival!

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Last updated: 08/01/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:6 nights
  • Internet:Yes
  • Pets considered:Ask Owner
  • Wheel chair accessible:No

Property description


If you like Captiva ... you will love Useppa & Hemingway Cottage -- a small, exclusive island just north of Captiva where one steps back in time.

History: The developer of South Sea Plantation decided he did not want to reside at South Sea. As beautiful as it was , the thought of living with 900 time share owners started him looking at near by islands where he found Useppa. Useppa is home to 100 plus lucky island cottage owners and guest with resort facilities like The Barron Collier Inn -- a large club house, spa, & health Club.

The island used to be totally private and 50 years ago did not allow kids. Today, that has all changed and families are the norm. The Lady Chadwick leaves daily from South Sea Plantation for Useppa Island with a load of Captiva tourist ---sadly they must leave after lunch and a quick tour of the island's famous musium.

The best way to get there is to take a prearranged Mom & Pop Van service from the Airport (RSW) to the island's private ferry- port out of Pine Island. Check with the owner for details and Ferry schedules. It leaves 4-5 times a day but water taxies are available if you arrive late. No need to rent a car.

The island is not for everyone but if you like Captiva you will love Useppa. Some say, it is like having all of the best of Captiva on your very own plantation. For others, it is a step back in History when Florida living was at its finest.

There are 3 restaurants, pool, hot tubs, free fishing tournaments on most Sundays for kids, Clay tennis courts and English wicket (couquet) for adults. Just bring your whites.

Fishing off the docks can not be beat and the Ferry Captains will bring you shrimp daily for the asking. There is a ships store for those oft forgotten and can't do without items like wine and cheese. Yes, one can still stay in touch with the world and purchase a US Today or local paper along with a cup of coffee and conversation at the ships store every morning.

There are no cars or crowds so walking, biking, golf carting is the normal mode of transportation. You can rent bikes, kyaks and golf carts on the island.

There are plenty of island staff when you arrive and they will get you setteled. They will meet the ferry and take you to Little Hemingway Cottage. There are no better sun sets than looking over the intercoastal while sail boats are setting anchor for the evening. The sun sets from Hemingway are historic as one views the sun set over these barrier islands as the Calusa Indians did 10,000 years ago.

Keywords: Hemingway, Cottage, Waterfront, Sunsets, Tropical, Island Time, Ferry boats, Privacy, Guilded, Tarpon bar, Snails Pace.

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Property Type

  • Cottage

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Non Smoking Only
  • Not Suitable For Children
  • Wheelchair Inaccessible

Bedrooms: 2 Bedrooms, Sleeps 6, Beds for 4-6

  • Bedroom 1


  • Convertible bed(s)

    Hemingway Trundel in pvt lock off Bonus Room -- sleeps 2...moreless

  • Bedroom 2: 1 queen

    Quensize adult This end up -- lower bunk -- sleeps 2...moreless

  • King size bed (1), -- master - sleeps 2 Queen size adult This ENd Up Bunk Bed BR # 2 - sleeps 2 + 1 Hemingway Trundle Couch -- sleeps 2...moreless

Bathrooms: 2 Bathrooms, 1 Half Bathroom


  • Satellite / Cable
  • Stereo
  • Television:

    one for each Bed Room Total 3...moreless

  • Video Games
  • Video Library


  • Museums
  • Restaurants

Local Services & Businesses

  • Fitness Center

Leisure Activities

  • Boating
  • Shelling
  • Wildlife Viewing

Location Type

  • Oceanfront:

    Hemingway Cottage over looks the Gulf and the Intercoastal waterway which is always funn to think about where the big ships so close to you are heading. The views are fantastic. See photos...moreless

Sports & Adventure Activities

  • Basketball Court
  • Cycling
  • Fishing
  • Swimming
  • Tennis


  • Dining:

    18 century Spanish pine table from Spain...moreless

  • Dining Area
  • Seating for 6 people


  • Air Conditioning:

    3 ton plus supplemental A/C & heat for Master B/R. ...moreless

  • Clothes Dryer
  • Fireplace:

    3 hour fire logs only...moreless

  • Fitness Room / Equipment:

    Separate facility is available -- no extra cost....moreless

  • Hair Dryer
  • Heating:


  • Internet:

    Available near by. Highly suggest bringing a "hot spot" for now,....moreless

  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking:

    Parking on Mainland provided. Golf cart provided at home....moreless

  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet:

    Highly suggest bring a "Hot Spot" from your tele carrier until Island gets WIFI Tower completed. ...moreless


  • Catering Available
  • Coffee Maker:


  • Cooking Utensils
  • Dishes & Utensils:

    Fully Stocked...moreless


  • Balcony
  • Bicycles:

    Available to rent on Island ...moreless

  • Boat:

    Available for rent at Four Winds Marina...moreless

  • Deck / Patio
  • Kayak / Canoe:

    Available for rent at Club...moreless

  • Outdoor Grill
  • Tennis:

    Available -at Club - No charge -- Clay Courts oly Must have proper attire for clay couirt. ...moreless

Pool / Spa

  • Communal Pool
  • Shared Hot Tub:

    Communal _ First Class -Out Door Facility...moreless



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Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
6 night min stay
$2,800 $8,000
* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates


  • Refundable Damage Deposit $1,000


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Last updated: 08/01/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates

Owner info

Year Purchased: 1996

About the owner: Retired Airline Captain. Adopted 5 older kids from Russia.

Why the Owner Chose Captiva, FL, USA:
Wanted to find a place where people from Florida went to 'get away.'

The Unique Benefits at this Cottage:
THe Last of Old Florida! Visiting Useppa is a step back into time --- possably a better time. You will get to decide.

Contact us

Speaks: english




  • Waterfront Master Bed Room

    Waterfront Master Bed Room

  • Waterfront dining

    Waterfront dining

  • Sunsets from Hemingway Dock

    Sunsets from Hemingway Dock

  • Sandy Beaches of Useppa

    Sandy Beaches of Useppa

  • The Historic Barron Collier Inn

    The Historic Barron Collier Inn

  • Massive waterfront view from Little Hemingway!

    Massive waterfront view from Little Hemingway!

  • Elegant homes line the beach on Useppa Island.

    Elegant homes line the beach on Useppa Island.

  • Fully equiped  Kitchen

    Fully equiped Kitchen

  • Lady Chaddwick arriving Useppa Docks daily from Captiva Island

    Lady Chaddwick arriving Useppa Docks daily from Captiva Island

  • Chushed pink conk shell paths run thru out the island with trophy
Banyan trees

    Chushed pink conk shell paths run thru out the island with trophy Banyan trees

  • Waterfront & poolside dining at the Collier Inn

    Waterfront & poolside dining at the Collier Inn



VRBO #387529

This listing was first published here in 2011.

Date last modified - Monday, August 22, 2016

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Member since: 2011
Speaks: english
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  • Response time Within 12 hours
  • Response rate 100%
  • Calendar last updated 08/01/2016
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Hemingway Cottage Sunsets Await Your Arrival!

Captiva, FL, USA #387529

2 BR  2.5 BA  Sleeps 6

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