Nightly Vacation Rentals

Nightly Vacation Rentals

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Key West Nightly Vacation Rentals

1 Bedroom | 2 Bedroom | 3 Bedroom | 4+ Bedroom


One Bedroom Nightly Vacation Rentals


Key West Nightly Vacation Rentals

1 BR / 1 BA, Sleeps Up to 4

Island Style – Vacation Suite

Resort style accommodations at an affordable price! Island Style is one of our most popular properties, a conch cottage nestled among lush tropical landscaping and a shared oasis style heated pool. Two fabulously funky sisters decorated the one-bedroom, one-bath condo, bringing to life the bright Caribbean colors and charm of Key West with art and hand-made furniture from Key West galleries.

$228 to $478

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1 BR / 1 BA, Sleeps Up to 6

Orchid Suite – A Relaxing Retreat

Orchid Suite is a two-level condo decorated in rich contemporary style. The bedroom is upstairs with a large bookcase divider that separates two sleeping areas, each with a queen bed. The upstairs bath has a tiled shower with glass door, hair-dryer and linens. Large beach towels also are provided for use at the shared pool, which is just a few steps away through a cute courtyard with a fountain.

$228 to $418

Hidden Oasis Vacation Rental

1 BR / 1 BA, Sleeps Up to 4

Hidden Oasis – Two Blocks from Duval St.

Tucked among a colony of Conch cottages, amidst lush tropical landscaping, you will find Hidden Oasis. The one-bedroom, one-bath property features a full kitchen, living room with queen sleeper sofa, cable TV, WiFi, DVD, gas BBQ grill and shaded private deck with outdoor dining. Just steps away is a shared oasis-style, heated pool — all at a great nightly rate. Hidden Oasis is on a quiet street, but also just two short blocks from world famous Duval Street. Off Street parking is available.

$228 to $478

nightly key west vacation rentals

1 BR / 1 BA, Sleeps Up to 4

Bella Vita – Vacation Suite

Located half a block from infamous Duval St, this beautiful 1 bedroom, one bathroom property is perfect for an island getaway. There are plenty of shops and restaurants well within walking distance, or if you prefer making meals yourself, it comes with a fully equipped kitchen.

$188 to $388

nightly key west vacation rentals

1 BR / 1 BA, Sleeps Up to 4

La Dolce Vita – Vacation Suite

Located half a block from infamous Duval St, this beautiful 1 bedroom, one bathroom property is perfect for an island getaway. There are plenty of shops and restaurants well within walking distance, or if you prefer making meals yourself, it comes with a fully equipped kitchen.

$188 to $388

La Casa Cubana

1 BR / 1 BA, Sleeps Up to 6

La Casa Cubana – Vacation Suite

Just steps around the corner from world renowned Duval Street, this spacious 1-bedroom property was built in 1917 as a “club” for Cuban cigar makers. It is so relaxing and beautiful, that you will never want to leave! The breezy private balcony is a great place to sit and soak up the rising sun with a cup of coffee as Duval Street buzzes with morning activity. The bedroom upstairs features two comfortable queen beds, a 32-inch flat screen TV, two large closets and a shared nightstand with a reading lamp.

$208 to $395

1 BR / 1.5 BA, Sleeps Up to 6

Bonaire Suite

The Bonaire Suite  is a bi-level suite decorated in a rich contemporary palm tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door.

$228 to $418

1 BR / 1 BA, Sleeps Up to 2

La Casa de Luna – A Getaway By Duval

Located in the heart of historic Old Town Key West, just steps away from world renowned Duval Street, La Casa de Luna is a  ground level, one-bedroom, one-bathroom condo that is part of a large house with a relaxing veranda. The master bedroom features a king bed, flat screen TV and two nightstands with reading lamps. The living room has comfortable island-style seating and flat screen TV.

$198 to $299

Island Pearl

1 BR / 1 BA, Sleeps Up to 2

Island Pearl – Perfect Key West Getaway

This charming cottage is your perfect Key West getaway.
When you enter through the gate you are greeted by the big shared pool and tropical foliage. The cozy cottage offers a a kitchenette and a trundle bed in the living room. There is a full bath downstairs and a queen size bed in the loft.

$248 to $558

Starr's Suite

1 BR / 1 BA, Sleeps Up to 2

Starr’s Suite – Abbey Road Collection

Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner JennAir cook top, dishwasher, under counter refrigerator, microwave and everything you need to prepare meals. Your private, gated courtyard has table and chairs and wonderful mood lighting and a top-of-the-line Solana 2 person Hot Tub with back and foot massagers.

$298 to $598

Abbey Road McCartney's Manor

1 BR / 1 BA, Sleeps Up to 2

McCartney’s Manor – Abbey Road Collection

Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner JennAir cook top, dishwasher, under counter refrigerator, microwave and everything you need to prepare meals. Your private, gated courtyard has table and chairs and wonderful mood lighting and a top-of-the-line Solana 2 person Hot Tub with back and foot massagers.

$298 to $598

Honeymoon Hideaway Key West Nightly Rental Suite

1 BR / 1 BA, Sleeps Up to 2

Honeymoon Hideaway – Center Court Collection

The kitchen offers an under-counter fridge, microwave, coffee maker, toaster, blender and everything to cook, prepare and enjoy a light meal. Also included is coffee, sugar, cream, foil, wrap and ziplock bags for your convenience…and don’t forget the BBQ grill and Ice-maker by the pool!

$298 to $598

Romantic Retreat Key West vacation rental for 2 in downtown Key West, FL

1 BR / 1 BA, Sleeps Up to 2

Romantic Retreat – Center Court Collection

Romantic Retreat features a king pillow-top bed, Tommy Bahama furniture, Bose Bluetooth speaker, flat screen TV and tropically inspired original fine art. The kitchen includes granite counter tops, under counter refrigerator, microwave, toaster/oven, coffee maker, blender and soft mood lighting under and above the cabinets.

$298 to $598

Sunset Suite Key West Nightly Vacation Rental

1 BR / 1 BA, Sleeps Up to 4

Sunset Suite – Center Court Collection

Overlooking the gardens and fountain in a gated 5-unit compound, the entrance to our spacious Sunset Suite is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous original tropical art by famed tropical artist, Dan Goade.

$198 to $458

Harrison's Hideaway vacation rental

1 BR / 1 BA, Sleeps Up to 2

Harrison’s Hideaway – Abbey Road Collection

Part of 4 exclusive units at Abbey Road, this free standing historic cottage is at 918-920 Center Street, features a king pillow-top bed, a full kitchen which includes a full stove and oven, refrigerator with ice-maker, microwave and dishwasher. It also includes a top-of-the-line Solana 2 person hot tub with back and foot massagers in your own private gated courtyard with table and chairs to delight your senses after a busy day of exploring our wonderful little town.

$198 to $458


Two Bedroom Vacation Rentals | Back to Top


Salacia--003

2 BR / 2 BA, Sleeps Up to 6
Weekly Only

Salacia at Key West Beach Club

Salacia is a two-bedroom, two-bath waterfront condo that has been newly renovated to provide a relaxing retreat with all the comforts of home: central air conditioning, cable TV, washer/dryer, WiFi and a fully equipped kitchen with quality dishes, glassware and cutlery. Imagine enjoying morning coffee, an afternoon cocktail or an evening meal of stone crabs on a spacious and comfy third-floor balcony with refreshing sea breezes and a gorgeous view of the Atlantic Ocean.

$225 to $450

Cuban Club Suites Key West Vacation Home Rental

2 BR / 2 BA, Sleeps Up to 6

Cuban Club Suite – A Classic Island Retreat

Built in 1917 as a “club” for Cuban cigar makers and their families as their “home away from home”, it soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. The Cuban Club Suites stands as an award winning historical landmark converted to spacious and luxurious two bedroom suite filled with all the amenities of comfortable living.

$225 to $450

Cuban Paradise vacation rental on Duval Street Key West

2 BR / 2 BA, Sleeps Up to 6

Cuban Paradise – A Classic Retreat on Duval Street

Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy two-bedroom condo has a private balcony to enjoy all the hustle and energy of the famous Duval Street. The master bedroom sits in a loft that overlooks the living room. It features a four-post queen bed, two nightstands with reading lamps, private bathroom, large closet and a small electronic safe. Located downstairs is another bedroom with a queen bed, a nightstand with reading lamp, large closet and flat screen TV.

$258 to $598

nightly key west vacation rentals

2 BR / 2 BA, Sleeps Up to 6

Island Breeze at 1800 Atlantic

Island Breeze makes a wonderful home base as you prepare to venture out into all that Key West offers. Escape to the luxury of Island Breeze at 1800 Atlantic in the paradise of Key West’s Atlantic coast. This semi-secluded condo is a getaway you won’t forget. Walk into the tranquil textures of tile floors underfoot as you view the soothing colors that fill the environment with cool tropical colors, natural browns and greens, and smooth cream and copper.

$275 to $450

Tortuga Hammock at Coral Hammock vacation rental in Key West, FL

2 BR / 2.5 BA, Sleeps Up to 4

Tortuga Hammock

Tortuga Hammock is a two-story, high-end vacation home in a private, gated community just minutes from all the fun and excitement of Old Town Key West. Accommodating up to 4 persons, it features two queen bedrooms (each with TV, en-suite bath, one with tub, the other with shower) upstairs, full kitchen, living room with 25” TV, DVD/VHS, stereo w/CD and half bath downstairs. Not even 1 mile from Key West proper, this gem is hidden right off of US 1. All new construction, this 2 bedroom-2-1/2 bath home is less than 500 yards from Murray Marina where you can dock your boat and across the street from the Rees Jones public golf course.

$288 to $425

Sunrise Suites Key West vacation rental 2 Bedroom 2 Bath

2 BR / 2.5 BA, Sleeps Up to 6

Sunrise Suite #203

Sunrise Suite 203 is a quiet alternative to the bustling noise of downtown Key West. Located just a 10-minute drive from all of the nightlife, shopping, restaurants and activities of world-famous Duval Street, Sunrise Suite is your own private condo in our island paradise.  You will enjoy the conveniences of a hotel with the comforts and space of home.

$175 to $379


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2 BR / 1 BA, Sleeps Up to 6

Fleming-O

Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and only two blocks from world famous Duval Street and its restaurants, bars, art galleries and shops. This completely upgraded Conch Cottage has all the modern amenities you would expect. Glass sliding doors open to a fenced, private deck that includes a gas grill, two chaise lounges, built-in benches and outdoor dining table.

$198 to $498

2 BR / 2 BA, Sleeps Up to 6

Mango Cottage – A Perfect Key West Hideaway

This recently-restored historic Conch house is an excellent vacation home. This fantastic home is located on Varela Street and is in a wonderful residential neighborhood just a couple blocks from Fausto’s Food Market and a short walk to Duval Street. It is also just a short walk to Higgs Beach, the White Street Pier and Key West Garden Club’s Civil War Fort West Martello.

$248 to $558

Hidden Treasure vacation rental

2 BR / 2 BA, Sleeps Up to 6

Hidden Treasure – A Perfect Key West Hideaway

Decorated in the vibrant colors of the Caribbean, and with artwork from local galleries, Hidden Treasure has a laid-back vibe. With two master bedrooms, each with a king bed and own full bath, and a queen sleeper sofa, Hidden Treasure is perfect for a family, two couples or a girls getaway. Double French doors open to a large private deck with two tables, seating for 10 and two lounge chairs. What a wonderful place to relax with a cocktail after a dip in the pool or enjoy a meal cooked on the outdoor grill.

$298 to $598

La Casa De Luces

2 BR / 2 BA, Sleeps Up to 6

La Casa De Luces – A Perfect Key West Hideaway

La Casa De Luces is a roomy, ground-level, two-bedroom, two-full bath property located in the heart of Old Town Key West. It’s perfect, whether you  are coming to the island paradise to relax, play or do both. A private, enclosed patio and a porch with comfortable chairs beckon you to unwind. The master bedroom features a king bed, 32-inch flat screen TV, and two nightstands with reading lamps. The second bedroom features a queen bed and a flat screen TV.

$198 to $458

Lennon's Lodge Abbey Road vacation rental in Key West, FL

2 BR / 2 BA, Sleeps Up to 6

Lennon’s Lodge – Abbey Road Collection

Lennon’s Lodge features the original Cuban tile preserved throughout the house. The state-of-the-art kitchen includes granite counter tops, stove, dishwasher, double door refrigerator/freezer, microwave and soft mood lighting under and above the cabinets. Your private rear deck with retractable awning has wonderful palms and indigenous vegetation surrounding the outdoor dining table, sofa and chairs, hot tub and outdoor shower. This is a great gathering area if you are renting all of Abbey Road for a large group!

$198 to $458

Family House Key West vacation rental home downtown Key West

2 BR / 1.5 BA, Sleeps Up to 6

Family House – Center Court Collection

This two-story 1880’s Cigar Maker’s Cottage has been completely renovated and has a living room with 42′ flat screen TV/DVD, Queen sleeper sofa with memory foam mattress. The kitchen is equipped with everything you need to cook a gourmet meal. The Family House is a unique gem hidden in a quiet oasis, perfect for the family looking for an upscale vacation all the features of your own home! Come visit us!

$198 to $458


Three Bedroom Vacation Rentals | Back to Top


nightly key west vacation rentals

3 BR / 2.5 BA, Sleeps Up to 8

Casa Loca – A Classic Caribbean Retreat

Case Loca is perfect for the discriminating guest who wants to enjoy the finest Key West has to offer! Located just one block from Duval Street, this 3-bedroom, 2.5-bath house will amaze you with its extraordinary decor and attention to detail! Sit on the fabulous island style porch and enjoy the tropical scenery.

$495 to $895

nightly key west vacation rentals

3 BR / 3 BA, Sleeps Up to 10

Royal Escape 

With high ceilings, hardwood floors, comfortable  furniture and a 46-inch HDTV in the living room, you’ll know you’ve arrived in paradise as soon as you walk in the door.  Two of the three bedrooms have a direct access to the deck and pool.  With an added bonus of off-street parking for your car, scooter or cab on call, this three bedroom, three bath tropical retreat is the ultimate “Royal Escape”.

$495 to $895

Absolutely Paradise vacation rental in Old Town Key West

3 BR / 2.5 BA, Sleeps Up to 8

Absolutely Paradise

Absolutely Paradise is a hidden oasis perfect for relaxing after a fun time on Duval Street. This town home is the perfect place to enjoy the tranquility of an island paradise vacation, while still located in the heart of Old Town Key West. The living area has an open floor plan, comfortable seating, hardwood floors and ceiling fans. The kitchen features all the modern amenities needed for coffee in the morning to whipping up a gourmet meal at night. There is a dining area that seats eight and a bar with four stools.

$495 to $895

Windsor Townhomes Key West Rentals

3 BR / 3.5 BA, Sleeps Up to 6

Windsor Townhome #4

One of these six newly complete town homes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. The villas are equipped with central air conditioning system, High Definition Flat Screen TVs, High Speed Wireless Internet Access, a DVD player, security system, and fully equipped kitchen. These elegant villas are a destination for those expecting a special and exclusive holiday with the warm atmosphere of your own home!

$495 to $895

Windsor Townhome Vacation Rental in Old Town Key West

3 BR / 3.5 BA, Sleeps Up to 6

Windsor Townhome #5

One of these six newly complete town homes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. The open living/dining area features comfortable sofas & chairs, with a dining table that seats six.  Sliding doors open from the living area to an inviting deck and pool that is surrounded by tropical plants, providing a relaxing ambiance for conversation after a day of sightseeing and adventure.

$495 to $895

Key West vacation townhome Windsor Townhome #6

3 BR / 3.5 BA, Sleeps Up to 6

Windsor Townhome #6

One of these six newly complete town homes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. The open living/dining area features comfortable sofas & chairs, with a dining table that seats six.  Sliding doors open from the living area to an inviting deck and pool that is surrounded by tropical plants, providing a relaxing ambiance for conversation after a day of sightseeing and adventure.

$495 to $895

Casa Margarita Luxury vacation rental home in Key West

3 BR / 3 BA, Sleeps Up to 8

Casa Margarita

Casa Margarita is the perfect luxury retreat if you are looking for a peaceful place that also is in the heart of Old Town Key West. This three-bedroom, three-bath home features a large backyard with lush tropical landscaping, a heated pool and a large hot tub.

$495 to $895


4+ Bedroom Vacation Rentals | Back to Top


nightly key west vacation rentals

4 BR / 4 BA, Sleeps Up to 12

Mermaid Cove

Located at the artsy 1200 block of world famous Duval Street, Mermaid Cove is the ideal affordable getaway for your Key West vacation. Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decorated and furnished in charming tropical fashion.  The units surround a central courtyard with outdoor patio furniture and a large gas BBQ grill. Mermaid Cove allows you to gather as a group, but also have privacy.

$395 to $995

Key West Hideaway Nightly Vacation Home Rental

Historic Ship Builder’s Home
4 BR / 4 BA, Sleeps Up to 10

Key West Hideaway

The newly renovated spacious kitchen features top of the line cabinets, granite counter tops and a pass-thru window to your private deck for al-fresco dining. The great room with a Queen sleeper sofa and 48” flat screen TV and DVD player features French doors opening to your private veranda overlooking the pool and gardens with outdoor dining table, ceiling fans and casual seating.

$495 to $995