Key West Florida Vacation Rentals, Hotels & Resorts


Top Floor Ocean Views from every window Newly Renovated

Key West Condo - 4.78344 4.8 Star Review

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY
Key West Paradise Found hes been renovated for 2020 and beyond. New Master Bathroom, Reconfigured Master Bedroom and Remodeled Kitchen. If you have a larger party we also own the 2 units right next door so they can all be rented together. Enjoy your luxury condo with breathtakin.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL

Key West Private vacation home - 5.0 5.0 Star Review

Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.

This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. The .......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

View Rental


Key West Coop - our tropical oasis in the Historic District close to everything

Key West Private vacation home - 5.0 5.0 Star Review

Beautifully remodeled Cottage in the Historic District of Key West. Walk or ride your bike to anywhere on the island. Close enough to enjoy the fun and frolic of Duval Street but far enough away to live like a local. Our home has two bedrooms and two bathrooms with the master suite upstairs with walk in shower. The guest bedroom and bathroom ar.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

View Rental


2019 Fantasy Fest Week 2 Bedroom 2 Bath Sleeps 6

Key West Condo

Rare Find to stay at Highly rated Coconut Mallory Resort and Marina during Fantasy Fest! 2 Bedroom fully equipped unit with Full kitchen. Unit has Flat screen TV in Living room with Cable and DVD and each bedroom has TV with cable and alarm clock. Balcony overlooks Marina and Pool and on-site Tiki Bar that offers refreshments. Close to Restaurants .......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Casa Key West- Rooftop Pool Access & Free Parking!

Key West Condo - 4.09091 4.1 Star Review

Summary:
This bright, spacious three bedroom condominium is the perfect Key West getaway. Located at Duval Square it is just steps away from fine dining, local shops and famous Key West attractions. There is a shared pool to enjoy and a private balcony to sit back and relax.

The Space:
Casa Key West is an open-concept 3 bedroom, 2 bath.......read more

3 Bedroom(s)
Sleeps 8
Condo

View Rental


A spacious "Penthouse" condo at The Banyan

Key West Condo - 4.4 4.4 Star Review

Just steps from Duval Street, this secluded resort appears off the beaten path, yet is truly situated a stone\'s throw from everything Key West has to offer. It’s got history, a crazy good location, awesome pools and jacuzzi, and it’s simply beautiful inside and out. If you’ve never been to Key West and you have this fantasy of what a tropical isl.......read more

Studio
Sleeps 4
Condo

View Rental


Waterfront Retreat, New Year’s Eve, 7 Nights, Sleeps 6, Beach, Boat Docks, Hyatt

Key West Condo

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key West. Envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal-clear water views. Enjoy the privilege of a private white sand beach, furnished with thick-cushioned chairs, picnic tables, ba.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Oceanfront Paradise! (15 minutes from Duval)

Key West Private vacation home - 5.0 5.0 Star Review

Stunning open water views from this beautiful oceanfront home. You can enjoy quiet mornings and spectacular sunsets.

The home features 2 bedrooms and 2 bathrooms. The master bedroom is equipped with a king size bed, and attached master bathroom. The guest bedroom is furnished with a queen size bed. Second bathroom can be accessed from the ma.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

View Rental


Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West Condo - 4.75 4.8 Star Review

Located just 2 miles from picturesque Smathers Beach, this well appointed 2 bedroom, 2 bath condo is ideally situated in Key West. Explore all Key West has to offer, located just 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square.

This two bedroom condo features a spacious king primary suite with hardwoo.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Brand New! Luxury 4 Bedroom Condo at Bayfront Suites & Marina

Key West Condo - 4.68421 4.7 Star Review

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale .......read more

4 Bedroom(s)
Sleeps 8
Condo

View Rental


**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…

Key West Private vacation home - 5.0 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West\'s most exclusive gated community, lives a \'gem\' of a home that will surely capture your heart\'s desire from the moment you lay eyes on it. JASMINE JEWEL is .......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

View Rental


Tropical Escape at Sunrise

Key West Condo - 4.5 4.5 Star Review

Due to Covid 19, we thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR\'s: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV\'s, A/C, washer-dryer, workout center, .......read more

2 Bedroom(s)
Sleeps 5
Condo

View Rental


Key West Suites Hotel - Adam Scott Rote Suite

Key West Apartment - 4.75 4.8 Star Review

Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets.

The building once housed the Chrysler/Desoto.......read more

Studio
Apartment

View Rental


The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6

Key West Condo - 4.89844 4.9 Star Review

This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880\'s that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of a.......read more

2 Bedroom(s)
Sleeps 4
Condo

View Rental


Amazing Vacation! 4 Spacious Units! 3 Pools, Restaurant, Tiki Bar, Bike Rental!

Key West Hotel

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.

ATTENTION: The Resort Fee is not included in the daily r.......read more

4 Bedroom(s)
Sleeps 8
Hotel

View Rental


Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West

Key West Condo - 4.88462 4.9 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.

The number one reaso.......read more

2 Bedroom(s)
Sleeps 4
Condo

View Rental


Our Key West Dream in Seaport.

Key West Private vacation home - 4.88889 4.9 Star Review

Family home for over 20 years, we would like to share our home to those that want to relax, see an amazing sunset, and enjoy the life in Key West. It’s fully renovated, beautiful and peaceful. Enjoy, relax, and Vacation. The house is a true Key West home built in 1918, and one of the few that remains typical KW style. This home is located in histor.......read more

2 Bedroom(s)
Sleeps
Private vacation home

View Rental


"THE FICUS HOUSE" ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!

Key West Private vacation home - 5.0 5.0 Star Review

VINTAGE ISLAND PARADISE...
Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the midst of Old Town Key West. Elegant architectural design with an unmatched collection of artwork, this mature retreat creates a blissful ambiance. A well known ficus tree among the infinite landscape makes this the legendary "Fic.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

View Rental


BRAND NEW HOT TUB JUNE 2022 aboard Houseboat Haven

Key West House boat - 2.0 2.0 Star Review

Summary:
Experience Key West in a new way: aboard a luxury houseboat! The brand new hot tub aboard Houseboat Haven was replaced this June 2022!
From watching sunrise on the dock to watching sunset from the balcony, or enjoying one of the best happy hours in town, you won\'t even need to leave the Marina. Come aboard & see why life really is b.......read more

2 Bedroom(s)
Sleeps 6
House boat

View Rental


**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...

Key West Private vacation home - 5.0 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

If you’re looking for a Florida Keys home that rivals the seaside homes found in ‘Coastal Living’ magazine, look no further! COASTAL LOVING is an inviting two-story private home that offers a relaxing vacation setting and comfortable acc.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

View Rental


Key West's Crown Jewel

Key West Condo - 4.68421 4.7 Star Review

Key West\'s Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath with approximately 1350 square feet of living space. Guests will enjoy absolutely breathtaking ocean views and the colors of the sunset from the 35-foot balcony, as well as from both bedrooms and the living room.

The Living .......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


ANOTHER DAY IN PARADISE in the Truman Annex

Key West Condo - 4.35714 4.4 Star Review

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. This property is outfitted with washer/dryer, pots/pans, towels, linens,.......read more

2 Bedroom(s)
Sleeps 6
Condo

View Rental


Oceanview home with expansive decks and private pool in lush landscaping

Key West Private vacation home - 4.88889 4.9 Star Review

"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasis in a private waterfront retreat, with your own heated pool.
Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, .......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

View Rental


Luxury Villa with Large Pool in Exclusive Area 5 min from Beach

Key West Villa

An absolute dream home in the most highly sought after location of Key West - the Casa Marina. You will feel at home and never want to leave this thoughtfully designed home. The entire house has been meticulously, professionally redesigned. Located in the most exclusive area of Key West, steps away from the Atlantic beaches, great dining and entert.......read more

3 Bedroom(s)
Sleeps 6
Villa

View Rental


BLUE HEAVEN in the Truman Annex

Key West Condo - 4.57692 4.6 Star Review

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, .......read more

2 Bedroom(s)
Sleeps 4
Condo

View Rental


GREEN SPOT @ the Truman Annex

Key West Condo - 4.42857 4.4 Star Review

Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastefully decorated 2 bedroom 1 bath condo with views of the pool. | The master bedroom has a queen sized bed & the 2nd bedroom has 2 twin beds. The remodeled bathroom with a walk in shower enclosure. The fully equipped kitchen opens .......read more

2 Bedroom(s)
Sleeps 4
Condo

View Rental


**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…

Key West Private vacation home - 5.0 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Spanning an exclusive corner lot in the desirable Mid Town neighborhood of Key West is a stunning compound-style home designed as the ultimate vacation destination for a family or group of friends seeking privacy and quiet only a short b.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

View Rental


BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.

Key West Private vacation home - 4.80263 4.8 Star Review

You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This property doubles as our second home when we are in town. Renovations include new wood flooring, fresh paint, new kitchen with stainless appliances and granite tops. All furnishings and accessories are new. Private courtyard with sunde.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

View Rental


Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest

Key West Cottage - 5.0 5.0 Star Review

WELCOME TO TROPICAL JEWEL!



Imagine yourself staying in this immaculate restored home just two blocks away from the Historic Seaport. Relax on the front porch in Adirondack chairs while enjoying a cold beverage. This home has it all, from the beautifully decorated living room to the terrific loft that so is comfortable. The living ar.......read more

2 Bedroom(s)
Sleeps 6
Cottage

View Rental


New Listing-Key West Charmer!

Key West Private vacation home

This home was built in 1933 and was an original Key West shotgun house and has been beautifully restored. The house has been decorated uniquely and has a tranquil and beachy vibe.
Upon entry you have a front closed in office space or reading room. This room looks out to the lush landscape and is perfect for an early morning coffee or an afternoo.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

View Rental


Find many Hotel Options and hundreds of Beachfront Vacation Rentals in Key West.

Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. We have historic Key West Vacation Rentals, you may even find a Vacation Rental with Boat Dock or Boat Slip. Hundreds of properties to choose from, search for availability, photos, descriptions and best price. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest.

© Reservations Direct, Inc. - Florida Keys & Key West Vacation Rentals, Hotels & Resorts

About Us - Privacy - Top Florida Destinations - Best Vacation Spots - Car Rentals