Anne's Hideaway: Old Town 2 Bedroom Vacation Property for Rent in Key West Florida with Pool and Rents Monthly

Anne's Hideaway: Old Town 2 Bedroom Vacation Property for Rent in Key West Florida with Pool and Rents Monthly

Key West 2 bedroom monthly vacation rental sleeps 4 with pool and a easy walk to Mallory Square and Duval Street : Anne's Hideaway

Vacation Home in Key West Florida

1000 Southard Street
Bedrooms: 2 Bedrooms • Sleeps 4
Bed Arrangements: 2 Queens, 2 Fulls
Bathrooms: 2 Full Bathrooms
Living Space: 1000 sqft.
Location Setting: Waterfront - Nearby
Beach Access: Near a Beach
Air Conditioning: Yes
Pool: Pool (Private)
Internet: Internet Access
Television: Cable/Dish TV
Washer/Dryer: Yes
Map of Key West

Rates & Availability  
(Displayed in USD)

  • Monthly Rates from $5,000 to $13,000 per month
  • Minimum Stay: 30 Days

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Season Nightly Weekly Monthly
Aug 01, 2022 - Aug 31, 2022
Minimum Stay: 30 Days
n/a n/a $5,000
Sep 01, 2022 - Sep 30, 2022
Minimum Stay: 30 Days
n/a n/a $9,000
Oct 01, 2022 - Oct 31, 2022
Minimum Stay: 30 Days
n/a n/a $7,000
Nov 01, 2022 - Nov 30, 2022
Minimum Stay: 30 Days
n/a n/a $9,500
Dec 01, 2022 - Dec 31, 2022
Minimum Stay: 30 Days
n/a n/a $12,000
Jan 01, 2023 - Jan 30, 2023
Minimum Stay: 30 Days
n/a n/a $13,000
Jan 31, 2023 - Mar 02, 2023
Minimum Stay: 30 Days
n/a n/a $12,000
Mar 03, 2023 - Mar 31, 2023
Minimum Stay: 30 Days
n/a n/a $13,000
Apr 01, 2023 - Apr 30, 2023
Minimum Stay: 30 Days
n/a n/a $9,500
May 01, 2023 - May 31, 2023
Minimum Stay: 30 Days
n/a n/a $8,000
Jun 01, 2023 - Jun 30, 2023
Minimum Stay: 30 Days
n/a n/a $7,000
Jul 01, 2023 - Jul 31, 2023
Minimum Stay: 30 Days
n/a n/a $5,500

Property Description

For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and modern functionality. The pool and deck oasis are private and delightful. Two bedrooms mean you can invite your whole family or some close friends to share your good fortune (but only if you want to).

The first thing you'll probably want to focus on when you arrive is the very spacious back patio area, where you can enjoy sunshine, tropical breezes, and the indulgence of an outside shower. The expansive wooden deck, surrounded by lush foliage, features a heated, L-shaped pool with sparkling coral waterfall. And still there's plenty of room at either end for lounging, eating, and sipping a latté or margarita. Maybe one evening, as the sun sets ceremoniously over the island, you'll be inspired to barbeque some fresh local fish with Caribbean spices. The natural next step is to savor your meal alfresco at the table and chairs nestled under the sea blue market umbrella next to the pool. As if designed with outdoor living in mind (and of course it was), the home has three sets of doors for you to access and make the most of this open-air oasis.

Back out front, from the street view, the home's structure is accented with the tradition and authenticity of Bahama shutters and is partially secluded behind date and coconut palms. Once inside, the open floor plan spreads out beautifully before you: cathedral ceilings, white walls, and natural hardwood floors in matte finish, the rest in shades of grey highlighted by sudden splashes of yellow and red. The accent colors continue in a series of prints called Island Homes. The sense is very contemporary and bright yet relaxing. Standing with the front door behind you, your eyes naturally gravitate to the glass walls in the dining area and the kitchen area that give peeks of the sky, pool, and palms beyond, bringing ambient light and verdant views right into the living space.

Inside to the left is a comfortable conversation area tucked under two large windows. Two couches face each other over a black lacquered coffee table and black and white patterned area rug, making the perfect space for talking or for watching a movie or sports on the wide-screen TV. Of course there is cable and wireless high-speed internet. A white paddle fan whirs above, circulating air and adding a sense of tropical ambience. Contributing to cohesion and harmony, the same fans are included in the décor and functionality of every room in the house. A dining area comes next, delineated by a striking artisan chandelier suspended over a black lacquered table. Should an occasional passing rain shower drive you indoors, you can sit here to have a meal, play board games, or work The New York Times crossword puzzle.

To the right, two doorways lead to two bright, airy, and peaceful queen bedrooms. The beds are firm yet comfortable and piled with soft pillows that promise a great night's sleep. Adjacent to the first bedroom is a washer/dryer closet, linen shelves, and a full bath cleanly done in glass mosaic tiles. The second bedroom is the master with queen bed, en suite full bath, and glass door opening to the deck oasis. Both bedrooms feature ample closets for hanging clothes and dressers for folded articles, making it easy to move right in. Both have TVs for entertainment and paddle-style ceiling fans with lights, providing airflow and great illumination.

The kitchen features all the chrome appliances you'd want plus plenty of cupboard and counter space to accommodate meal preparation. And still there's room for a coffee bar with two tall red chairs. Sunlight pours through a double window while evening lighting is supplied by a surprising trio of metal pendant lights, two in grey and one in a striking yellow. The professional design rule here is the same as elsewhere: simplicity, functionality, delight.

Once you've explored your accommodations and put on suntan lotion, it's time to get to know your neighborhood and the rest of Key West. The Historic Seaport is only three streets over. There you'll find impressive tall ships like the Schooner Western Union, the official flagship of Key West and the State of Florida. She's one of the oldest wooden schooners in the United States. Her sister ships in the harbor offer day and sunset cruises where you can sip local spirits and munch hors d'oeuvres as your vessel carries you into sunsets like you've never seen before. Or you can walk the seaport boardwalk to Mallory Square to experience sunset from the shore. This is where crowds of visitors and locals alike gather daily to witness the sun sinking into the horizon. Be sure to applaud as the last round edge of fiery orange disappears at the horizon. Then hang around for the party as artists and street performers entertain the crowd.

From Mallory Square, the famous Duval Street is within two blocks in case you're interested in tours, museums, shopping, over two hundred restaurants, bars, and the Key West Aquarium where you can pet a shark if you dare. If less intimidating animals seem more appealing, try the Butterfly & Nature Conservatory.

To know what's going on from day to day, check out Historic Hideaways' informative Events page at Other information on the current music scene, movies, plays, gallery openings, and charitable events can be found at (calendar section) or in the print publication Paradise, which is available at various locations around town every Thursday.

Activities and Special Interests

This property provides access to the following activities and special interests:

» Beach
» Biking
» Boating
» Canoeing
» Fishing
» Deep Sea Fishing
» Golfing
» Honeymoon
» State National Parks
» Ocean
» Sailing
» Scuba Diving
» Surfing
» Fly Fishing
» Wind Surfing
» Hiking
» Kayaking

Featured Amenities

» Air Conditioning
» Cable/Dish TV
» Dishwasher
» Grill
» Internet Access
» Pool (Private)
» Washer/Dryer

Property Features

» Ceiling Fan(s)
» Coffee Maker
» Deck/Patio/Porch
» Dishes/Utensils
» Filtered Water
» Freezer
» Full Kitchen
» Ice Maker
» Microwave
» Oven
» Parking
» Refrigerator
» Towels/Linens

Other Property Amenities

  • Beach Distance: Biking
  • Bed Size 1st/Master: Queen
  • Bed Size 2nd Rm: Queen
  • Patio: Yes
  • Square Footage, Est.: 1,000
  • Air Conditioned: Central
  • Number of Baths: 2 Full
  • Outdoor Shower: Yes


The house was well equipped, very Key West!
—Patsy A.
July 2020
The house was well equipped, very Key West! It was clean. The large umbrella outside was a lifesaver. It rained a lot at the end of month while we were there. It is very close distance to Duval Street. Southard Street runs directly into it. Loved the outside shower!
Excellent location
—Rosalyn G.
February 2017
Excellent locationBeautifully furnished Very clean and comfortable. A better set of pots and pans would be useful.
The unit was pretty good overall...
—Michael M.
February 2016
The unit was pretty good overall and the service we got from Historic Hideaways (Tim) meant we booked for next year via you in an alternative property as the one were in as not available.
Guest Survey Has Been Completed
—Betty J.
January 2016
How would you rate this rental on:The quality of our website, ExcellentReservation Staff and Booking process? ExcellentEase of Check In? ExcellentValue of the Home? ExcellentLocation of the Home? ExcellentCleanliness of the Home? ExcellentComfort of the Home? ExcellentEase of Check-Out? ExcellentOverall Satisfaction with the Home? ExcellentOverall Satisfaction with Historic Hideaways? Excellent
The off street parking was very good.
—Kevin C.
January 2015
The location, next to 5 brothers, was very noisy early in the morning which was not good for us. The off street parking was very good.

  • anne's hideaway (30 night minimum) key west florida
  • anne's hideaway (30 night minimum) key west area
  • 2 bedroom home
  • sleeps 4
  • 2 bedroom vacation rental
  • florida vacation places to stay