Oceanfront Home on Summerland Key

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Last updated: 10/24/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:28 nights
  • Sleeps:10
  • Bedrooms:4
  • Bathrooms:3
  • Property type:House
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:N/A

Property description

This breezy island get-a-way, fashioned in the casual style of Key West & The Bahama Islands, is the perfect vacation spot for anyone seeking to rent a peaceful, charming and conveniently located beach cottage. Located on the ocean with its own private dock and beach, Windswept's first floor (unlike most Florida Keys homes on stilts) is ground level allowing easy access to the kitchen, living room, 2 bedrooms, 1 bath and a large screened in porch that stretches the entire waterfront side of the house. The upstairs has 2 bedrooms and 2 adjoining baths. Both upstairs bedrooms have sliding glass doors that open up to a large upstairs balcony with unending water views, a built in sitting area, and an outdoor staircase that leads to the beach.

Bring your boat or rent one and tie up at our new dock. There is also a convenient boat launch on Summerland Key. A vacation to remember for all ages and interests or the perfect hideaway for the artist/writer or fisherman.

Keywords: Beach House

Send email


Member since: 2009

Speaks: english
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 10/24/2016

Property Type

  • House

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Children Welcome
  • Limited Accessibility:

    downstairs living area...moreless

  • Pets Considered:

    Extra pet deposit may be required...moreless

Bedrooms: 4 Bedrooms, Sleeps 10, Beds for 10

Bathrooms: 3 Bathrooms

Other Amenities

  • 3 Kayaks, and 3 Bikes, are available for guest use.


  • Books
  • CD Player
  • DVD Player
  • Games
  • Satellite / Cable:

    (2) We have ComCast Cable...moreless

  • Stereo
  • Television:

    Main Living area has a new Large Screen TV. Each Bedroom, with the exception of the laudry room has their own TV....moreless

  • VCR
  • Video Library:

    TV Series Video's ranging from the Office to Sopranos...moreless


  • Cinemas
  • Health/Beauty Spa
  • Marina
  • Museums
  • Restaurants

Local Services & Businesses

  • ATM/Bank
  • Fitness Center
  • Groceries

Leisure Activities

  • Antiquing
  • Bird Watching
  • Boating
  • Horseshoes
  • Miniature Golf
  • Shelling
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Beachfront:

    Several chaise lounges and beach chairs are available for guests use. Dock has bait station and water hose. Tiki Hut for shade as well....moreless

  • Oceanfront

Sports & Adventure Activities

  • Cycling
  • Deepsea Fishing
  • Fishing
  • Golf
  • Jet Skiing
  • Kayaking
  • Parasailing
  • Pier Fishing
  • Sailing
  • Skiing
  • Snorkeling
  • Snorkeling/Diving
  • Swimming
  • Tennis
  • Water Skiing
  • Wind-Surfing


  • Dining Area


  • Air Conditioning
  • Broadband Access
  • Clothes Dryer
  • Hair Dryer
  • Iron & Board
  • Linens Provided
  • Parking Off Street
  • Parking For RV/Boat/Trailer
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet:

    Can work from the dock (by why would you want to?!)...moreless

  • Wood Fireplace:

    Fire Pit on the Beach...moreless


  • Catering Available
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Refrigerator


  • Balcony
  • Bicycles:

    3 bicycles for guests to use...moreless

  • Deck / Patio
  • Kayak / Canoe:

    3 kayaks for guests to use...moreless



Write a review 5
from 12 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
28 night min stay

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

Additional information about rental rates


  • Pet Fee $100
  • Refundable Damage Deposit $500
  • Tax Rate 17.5%


Per the County of Monroe Code Compliance - the mimimum stay for a renter is 28 days. Checks are the preferred method of payment if possible.

Owner's cancellation policy:

100% refund if canceled at least 30 days before arrival date.

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Last updated: 10/24/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


The turquoise waters offer excellent boating, snorkeling, fishing and all water sports. The end of the dock includes a tiki hut for shade and fish cleaning station. Looe Key, a premier diving reef, is located 6 miles out in the Atlantic and Little Palm Island (an exclusive island resort) is very close and available, by your boat or theirs, for a five star lunch or dinner. Fabulous shopping and dining are 20 minutes away in historic Key West.


Owner info

Year Purchased: 1940

About the owner: Managed by the children and grandchildren of the original owners who purchased the property in the 40's and built the house in the late 50's. House was expanded and renovated in the 90's.

Why the Owner Chose Summerland Key, FL, USA:
Property was inherited from original owners (third generation Conchs). The five owners have many children and grandchildren who occupy the house most of the time. The minimum stay in 28 days per the County of Monroe Code Compliance Department.

The Unique Benefits at this House:
Great area restaurants (Square Grouper, Mangrove Mama's, No-Name Pub) and Cuban cuisine (5 Brothers). Excellent fishing off the dock - with lighting to illuminate water at night!

Contact us

Speaks: english
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 10/24/2016

Send email

Links to more information:



  • Downstairs living area

    Downstairs living area

  • Upstairs Bathroom - Gumbo Limbo

    Upstairs Bathroom - Gumbo Limbo

  • Upstairs Bathroom - Frangi Pani

    Upstairs Bathroom - Frangi Pani

  • Downstairs Master

    Downstairs Master

  • Downstairs Bedroom/Laundry Room

    Downstairs Bedroom/Laundry Room

  • Dock and Beach

    Dock and Beach

  • Stairway


  • Screened porch

    Screened porch

  • Bar on Front Screened Porch

    Bar on Front Screened Porch

  • Beach side of house

    Beach side of house

  • Sunrise at Windswept

    Sunrise at Windswept

  • Storm Approaching....

    Storm Approaching....

  • Upstairs Bedroom - Gumbo Limbo

    Upstairs Bedroom - Gumbo Limbo

  • Upstairs Bedroom - Frangi Pani

    Upstairs Bedroom - Frangi Pani

  • View from upper balcony

    View from upper balcony

  • Updated Downstairs Master

    Updated Downstairs Master

  • Kitchen


  • View towards kitchen

    View towards kitchen

  • Screened porch sitting area

    Screened porch sitting area

  • Comfortable Porch Seating

    Comfortable Porch Seating

  • Porch Bar

    Porch Bar

  • Outdoor Dining

    Outdoor Dining

  • Sunset near Pie Key

    Sunset near Pie Key

  • Nice catch!

    Nice catch!

VRBO #249627

This listing was first published here in 2009.

Date last modified - Wednesday, October 26, 2016

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Oceanfront Home on Summerland Key

Summerland Key, FL, USA #249627

4 BR  3 BA  Sleeps 10

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