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Experience the Ultimate Getaway at Anchors Away - 3 Bedroom Vacation House

Home Rental in Key West Florida

Discover your private oasis at Anchors Away - a spacious 3 bedroom vacation house that offers the ultimate Key West getaway.

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Historic Hideaways
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Rates from
$143 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Anchor's Away is a 3-bedroom, 2-bath home in Old Town Key West, Florida Keys, sleeping up to 6 guests in about 1,400 square feet. Set in a town/village setting near a beach, it pairs a restored conch-cottage layout with a private outdoor focus, including a heated pool with a waterfall feature and an outdoor shower. The home is dog-friendly with stated restrictions and an additional pet fee.

Inside, the main level includes an open kitchen and dining area with granite counters, a breakfast bar, and seating for six, plus a living room with a large HD flat-screen TV and Wi‑Fi. Two queen bedrooms are on the first floor alongside a full bath, while the second-floor primary suite offers a king bed, its own full bath, and closet space. Outdoor living centers on a deck and garden area with French-door access, a gas grill, and space for meals outside.

Good fit for
Pet-friendly stays
Heated Pool Waterfall Heated pool includes a waterfall feature in the outdoor deck and garden area.
Sleeps Six Three bedrooms sleep up to 6 guests with 1 king bed and 2 queen beds.
Dog Friendly Dogs are allowed with restrictions and an additional $200 pet fee.
Outdoor Shower Outdoor shower is provided for rinsing off after pool time.
Open Kitchen Dining Open kitchen/dining area includes granite counters, breakfast bar, and seating for six.
At a glance

Property Highlights

Town / VillageLocation Setting
Near a BeachBeach Access
3 BedroomsBedrooms
2 Full BathroomsBathrooms
Sleeps 6Guest Capacity
1400 sq. ft.Living Space
PoolPool
Internet AccessInternet
TelevisionTelevision
YesPet Friendly
YesWasher / Dryer
Key West Florida
Location & nearby Explore the Area

Located in Old Town Key West, Anchor's Away sits on White Street near the intersection with Southard Street. The listing notes the home is near a beach and places you within the town/village setting of Key West. White Street runs across the island from the Gulf of Mexico to a fishing pier on the Atlantic side, and the description references nearby everyday conveniences such as art galleries, grocery options, fitness and yoga studios, and other local businesses along these corridors.

Plan your stay

Rates & Availability (USD)

Rates from
$143 per night
30-day minimum stay
Check current rates & availability

Live booking details are maintained by Historic Hideaways.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
Season Nightly Weekly Monthly
Oct 01, 2026 - Oct 31, 2026
Minimum Stay: 30 Days
$143 $1,001 $4,290
Nov 01, 2026 - Nov 30, 2026
Minimum Stay: 30 Days
$167 $1,169 $5,010
Dec 01, 2026 - Dec 31, 2026
Minimum Stay: 30 Days
$250 $1,750 $7,500
Jan 01, 2027 - Jan 30, 2027
Minimum Stay: 30 Days
$533 $3,731 $15,990
Jan 31, 2027 - Mar 02, 2027
Minimum Stay: 30 Days
$567 $3,969 $17,010
Mar 03, 2027 - Mar 31, 2027
Minimum Stay: 30 Days
$533 $3,731 $15,824
Mar 03, 2027 - Mar 31, 2027
Minimum Stay: 30 Days
$533 $3,731 $15,824
Apr 01, 2027 - Apr 30, 2027
Minimum Stay: 30 Days
$367 $2,569 $11,010
Apr 01, 2027 - Apr 30, 2027
Minimum Stay: 30 Days
$367 $2,569 $11,010
May 01, 2027 - May 31, 2027
Minimum Stay: 30 Days
$167 $1,169 $5,010
Jun 01, 2027 - Jun 30, 2027
Minimum Stay: 30 Days
$167 $1,169 $5,010
Jun 01, 2027 - Jun 30, 2027
Minimum Stay: 30 Days
$167 $1,169 $5,010
Jul 01, 2027 - Jul 31, 2027
Minimum Stay: 30 Days
$167 $1,169 $5,010
Jul 01, 2027 - Jul 31, 2027
Minimum Stay: 30 Days
$167 $1,169 $5,010
Aug 01, 2027 - Aug 31, 2027
Minimum Stay: 30 Days
$150 $1,050 $4,500
Sep 01, 2027 - Sep 30, 2027
Minimum Stay: 30 Days
$150 $1,050 $4,500
About this rental

About This Rental

Anchor's Away is a restored three-bedroom, two-full-bath home in Old Town Key West that sleeps up to six guests. The property is in a town/village setting and is listed as near a beach. With approximately 1,400 square feet of living space, it combines indoor comfort with a dedicated outdoor area built around a heated pool and waterfall feature.

The backyard is arranged for time outside, with French doors opening to a deck, garden, and pool area. Amenities include a gas grill for outdoor cooking and an outdoor shower for rinsing off after time in the pool or out for the day. The home also includes parking, internet access, and a washer/dryer.

Indoors, the kitchen and dining area are designed as an open-flow space. The remodeled kitchen includes granite countertops, a dishwasher, microwave, and other appliances, along with a breakfast bar. The dining table seats six. The living room provides a large HD flat-screen TV and Wi‑Fi for downtime between outings.

Sleeping is arranged as 1 king and 2 queens. Two queen bedrooms are located on the first floor near a full bath. Upstairs, the primary suite includes a king bed and a private full bath. Dogs are allowed with restrictions (including limits on number/size and breed exclusions) and an additional pet fee of $200.

Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom, two-full-bath conch cottage in Old Town Key West. Recently restored and updated to include amenities such as a heated pool with rainforest waterfall, granite counter tops, and hardwood floors, you'll find plenty of comfortable living space here.

The back of Anchors Away, named with a nod and wink to the seafaring history of the Southernmost City, opens through French doors onto a secluded deck, garden, and pool area ringed by lush tropical vegetation that adds design, color, shade, and privacy. Refresh here with a swim or relax on one of the chaise lounges to the meditative sound of the waterfall or music from the outside speakers. Afterwards rinse off in the outdoor shower. Maybe the tropical climate will tempt you to grill some local black fin tuna or burgers at the gas barbecue and then enjoy your meal alfresco at the teak table and chairs overlooking this plethora of natural beauty and creature comforts. There's even an intimate lighting feature for your evening enjoyment.

Back through the French doors, you enter the open-flow dining and kitchen area highlighted by highly polished hardwood floors. The dining table easily seats six and offers a lovely view of the pool, so you feel you're eating in the open air even when you're not. The remodeled kitchen features new appliances in onyx that dramatically offset white cabinets. The natural granite counter curves around to end in a breakfast bar complete with stool chairs. It's a great place to enjoy a frothy latte or even a whole meal if you've already cluttered the dining table with beach coral or magazines or computer gear.

The first floor also provides two bedrooms. Walk through the door of the back one and you'll see a queen bed highlighted in coastal colors. French doors bathe the room in ambient light and give a lovely view of the garden and pool, not to mention easy access to the outside area. A Casablanca-type ceiling fixture provides a distinctive touch as it lights and cools the space.

Conveniently located next to the bedroom is a full bath done in natural stone wall tiles and smaller mosaic floor tiles. A generous window lets in light and, if you choose to open it, tropical air as well. Next to this bath, you'll find the carpeted staircase to the second floor, which leads you to a master bedroom suite with king bed, full bath, ceiling fan/light, and ample closet space. The wall-to-wall carpeting will delight your bare feet. The bedroom, like the kitchen, is done in a crisp white and dramatic black color scheme. Surrounding the bed are storage shelves and drawers for your vacation clothes and gear like flip-flops, cell phone, pedometer, camera, computer, hat, and sunglasses. The closet offers a spacious place to hang clothes and more shelf space above. The bedroom windows look out on White Street and the bath windows offer a pool and garden vista.

Back downstairs, the living room highlight is a large, overstuffed onyx leather couch great for serious cozying down. Sit here for conversation or to watch TV or a movie on the large HD flat screen or enjoy other aspects of the entertainment center, including cable, Wi-Fi, and TIVO. A whimsical red, tan, cream, and black area rug adds color and accents the red cube coffee table, which doubles as an ottoman.

The front bedroom, off the living room, also features a queen bed. The space is decorated in wicker and restful tones perfect for a tranquil night's sleep. Ample windows let daylight in and lamps and a ceiling fan/light illuminate the evening.

You'll be immensely pleased with the living space at Anchors Away. You'll be even more pleased by its location. You're near the intersection of two convenient corridors. The first is your street, White Street, which runs the fourteen-block width of the island from the Gulf of Mexico to a fishing pier jutting out into the wide Atlantic Ocean. On White you'll find art galleries, Faustos Food Palace, convenience stores, the Island Gym, yoga studios and yummy cupcakes at Key West Cakes, to name a few.

The second corridor is Southard Street, which takes you through a leafy residential neighborhood and past 5 Brothers Grocery and Sandwich Shop, a mom and pop establishment frequented by locals for breakfast and lunch. Five more blocks brings you to Duval Street, the central artery of entertainment. There you'll find what Key West is famous and infamous for: tours, beaches, museums, Mallory Square at sunset, water sports, shopping, bars, and over two hundred restaurants, many with open-air seating, some right on the water.This home is Pet (Dog) Friendly**(please see below or our FAQ page for rules and restrictions)

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

**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.
Things to enjoy

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
Pet Friendly
Sailing
Scuba Diving
Surfing
Theatre
Fly Fishing
Wind Surfing
Family Vacations
Kayaking
What's included

Property Amenities

Featured Amenities

Dishwasher
Grill
Internet Access
Pets Allowed
Television
Washer/Dryer
Pool

Property Features

Ceiling Fan(s)
Microwave
Parking

Other Property Amenities

Bed Size 1st/Master: King
Bed Size 2nd Rm: Queen
Bed Size 3rd Rm: Queen
Number of Baths: 2 Full
Square Footage, Est.: 1400
Patio
Stereo System
Air Conditioned: Split Systems
Outdoor Shower
Beach Distance: Biking
Dog: w/ restrictions - see FAQs
Helpful details

Frequently Asked Questions

Anchor's Away is located in Key West, Florida.

Anchor's Away accommodates up to 6 guests.

3 Bedrooms and 2 Full Bathrooms.

The listed beach access for Anchor's Away is Near a Beach.

Yes. The property lists Pool.

Yes. Anchor's Away is listed as pet friendly. Review the manager's policies for any pet restrictions or fees.
Local management

Professionally Managed By

Historic Hideaways
In business since 1996
View Manager Profile

Questions about this rental?

Connect directly with Historic Hideaways for current rates, availability, and local assistance.

Contact Reservations and Guest Services at Historic Hideaways
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Property reference
#123662 · Anchor's Away
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