2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the ...
Property Type
Key West House
Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the ...
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is ...
Property Type
Key West House
My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The ...
1 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 0.2 miles to Public Beach is Smathers
Key Amenities
About this property
Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Key West! .....it’s not just a place on the map, it’s a frame of mind, an Attitude…… come and let us share that Key West Attitude with you!Fully Renovated This is a Luxury ...
Property Type
Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Once you see this historic two storey townhouse, you won’t want to stay anywhere else!Filled with natural light, this end unit is ‘tucked away’ in an exclusive, historic Foundry building next to the ‘Truman Little Whitehouse’. There are only 3 residences in our building!There ...
Property Type
Key West Townhome
I almost don’t want to write this as I’d like to keep it for myself! This extra special house is truly one of a kind. It’s beautifully appointed with so much care given to the decor. It’s truly ...
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos ...
Property Type
Key West House
Key Amenities
About this property
Enjoy the ocean views from this beautifully appointed condo in the exclusive Key West Beach Club.This two-bedroom, two and half-bath waterfront condo that has been newly renovated with casual furnishing and all the comforts of home: central air conditioning, cable TV, washer/dryer, Wi-Fi, and a fully-equipped ...
Property Type
Key West Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, ...
Property Type
Key West House
The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used ...
5 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants ...
Property Type
Key West House
I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away ...
Studio | 1 BA | Sleeps 2 | Quick View
Distance to beach: 0.5 miles to South Beach
Key Amenities
About this property
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill ...
Property Type
Key West Condo
This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...
1 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the ...
Property Type
Key West Condo
Key Amenities
About this property
The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...
Property Type
Key West House
The heated pool, tiki bar and view of the ocean was just beautiful as "out of a storybook. The eggs and a home made lime pie from Carol (owner) was a nice surprise. The house was plenty big enough to house ...
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Looking to Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...
Property Type
Key West House
We loved this house at the end of a quiet lane. Huge pool! The location was perfect, walking was easy to so many places. Fully fenced and a small backyard made it perfect for our dog. And the shower ...
Studio | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, and one of the best people watching front porches in Key West. Steps from the water, just 3 blocks from Duval street, and surrounded by ...
Property Type
Key West Studio
We stayed at this property for 6 weeks. The location is awesome! It is steps away from the marina, a short walk to a small beach, and just several blocks from Duval Street. The location is also set in close ...
Key Amenities
About this property
Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside ...
Property Type
Key West House
The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...
2 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach
Key Amenities
About this property
Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always received great reviews on cleanliness and the bright citrus pallet is welcoming, there are 2 bedrooms (1 King & 1 Queen), one bathroom with couples walk in shower, The small but ...
Property Type
Key West Condo
6 BR | 7 BA | Sleeps 16 | Quick View
Distance to beach: 0.3 miles to Ft Zachary Taylor
Key Amenities
About this property
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...
Property Type
Key West Villa
We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not ...
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Overlooking the Historic Key West Bight Seaport, this large 1/1 with King sized bed features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, new split unit AC, high speed internet, right in the middle of it all! Steps from the water, just 3 blocks from Duval street, ...
Property Type
Key West Apartment
We have stayed with this host numerous times and can not say enough about them as well as this particular space and location. If you are looking for a true taste of Key West look no further. This building ...
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Blue Haven: An Exquisite Oceanfront Penthouse – Complete Remodel with Direct Ocean Views and Massage Chair – Premier Unit on Property Blue Haven is the premiere property in this complex. This luxury penthouse condominium is unbelievable. You will not want to leave. Nestled on the shore of ...
Property Type
Key West Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to Higg's Beach
Key Amenities
About this property
Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district ...
Property Type
Key West House
We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more. ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 30 feet to property 20 yards from ocean, 4 mile white sand be
Key Amenities
About this property
Please contact the owner for stays less than 28 days before you try to book . In Key West - Not Islands Away *** Ocean Front**Ocean View from Every Room *90' Scenic Balcony Huge 2200 Sq Ft under air. This is a $1.5 Million Dollar Property with priceless View!***SPECIAL REDUCED RATES FOR ...
Property Type
Key West Condo
Love these condos !! Second time to same place!! Great escape from Seattle. Family friendly. Great food.
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Location Location Location....Close to Duval and Beaches! Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Key West Historic ...
Property Type
Key West Bungalow
Key Amenities
About this property
Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying ...
Property Type
Key West Townhome
Excellent property; highly recommended. Holly is an amazing host: very responsive and accommodating. She provided detailed check in/out instructions, descriptions of the property amenities, and a tour guide ...
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny ...
Property Type
Key West House
I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to ...
3 BR | 3 BA | Sleeps 7 | Quick View
Key Amenities
About this property
Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports ...
Property Type
Key West Townhome
We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf ...
Key Amenities
About this property
Tiki Tango - Your Key West Oasis in the Coveted Casa Marina District!Welcome to Tiki Tango, a grand 2-bedroom, 2-bathroom home that blends island ambiance with modern luxury. Located in the coveted Casa Marina District of Key West, this vacation rental promises a memorable stay with its private pool, ...
Property Type
Key West House
2 BR | 1.5 BA | Sleeps 4 | Quick View
Distance to beach: 2 miles to Smathers Beach
Key Amenities
About this property
Come stay in a premier development in Key West. If you're looking for a monthly stay of 28 days or more then this is the place. You would be close to everything Key West has to offer stay at our peaceful serenity of your temporary home in Paradise. Our house offers many amenities to make your stay ...
Property Type
Key West Townhome
The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in ...
Property Type
Key West House
We stayed a month in December(2022),had everything we needed,close to shopping,sightseeing, nightlife,beaches and airport. House is completely furnished and nothing is lacking.Pool was heated and had all ...
2 BR | 1 BA | Sleeps 5 | Quick View
Distance to beach: 0.2 miles to Fort Zachary Beach
Key Amenities
About this property
DISCOUNTED MONTHLY RATES. AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. POOL within 1 walk of condo108!! 5-STAR ...
Property Type
Key West Condo
Location was perfect as it is closer to the entrance of Truman Annex and in turn only steps away from Duval, Mallory Square and Truman Waterfront park. Owner's were very friendly, extremely responsive ...
4 BR | 2.5 BA | Sleeps 8 | Quick View
Distance to beach: 600 yards to Simonton Street Beach
Key Amenities
About this property
Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen ...
Property Type
Key West House
This property was absolutely amazing! Being in Old Town and just steps away from Caroline St and a few blocks from Duval was so convenient. We were traveling with our adult children and everyone could come ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Suncatcher on the ocean is new to the rental pool at 1800 Atlantic. A fabulous property with many upgrades throughout. Totally renovated from top to bottom with high end finishes and no attention to detail spared. We are excited to offer it for rent for the first time. Tastefully decorated in Island ...
Property Type
Key West Condo
4 BR | 4.5 BA | Sleeps 8 | Quick View
Distance to beach: 50 yards to One block from fantastic beach
Key Amenities
About this property
This one of a kind beautiful home was built in 1912 by one of the first cigar makers. It is listed on the National registry of historic homes and has been showcased in the Holiday Parade of Homes. The home was restored and expanded in 2002 Key West contractor Richard Manley with the highest level of ...
Property Type
Key West House
1 BR | 1.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price is generally half of what you would pay for a daily-rate comparable unit, and it gives you a lot more options and freedom.Located on a side street off Duval and ...
Property Type
Key West Townhome
This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...
Key Amenities
About this property
About this space Built in 2022, this vibrant, 1400 sq ft stilted home brims with personalized art and touches inspired by The Keys history, landscapes and local artisans. From this luxurious retreat you will enjoy a crystal-clear canal access, a private dock, a tropical micro pool, a stocked chef's ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 1 miles to Fort Zachery Taylor State Park
Key Amenities
About this property
924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy ...
Property Type
Key West House
Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great ...
Key Amenities
About this property
This 4 bed 3 bath home with spectacular ocean views is the perfect spot for your vacation. 1 King and 3 queen beds. There are 2 kayaks provided for your enjoyment. You may bring up to a 25' boat and dock at the seawall. The kitchen is fully stocked with all the essentials. Linens, towels and ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This condo has been beautifully renovated. Both bedrooms and the living room open onto a spacious 40 ft private balcony. There is a King Bed in the Master bedroom and 2 twin beds in the guest bedroom.1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City ...
Property Type
Key West Condo
Key Amenities
About this property
We specialize in amazing vacations and honeymoon and extended stays for two guests, aboard a yacht that stays dockside without the chance of seasickness allowing you to come and go according to your own schedule. Our pedigree Hatteras, a custom 60' motor yacht, a timeless classic designed for elegant ...
Property Type
Key West Yacht
The Paradise is a grogerous yacht. The woodworking is amazingly beautiful. The bed is very comfortable. We really enjoyed our stay and was very pleased. Captain Berry & Tamara were very tentative and superior ...
3 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. ...
Property Type
Key West Condo
THE KEYS TO PARADISE CONDO IS SO WONDERFUL. The view is Breathtaking. The condo is well kept and clean. It has beautiful furnishings and distinctive artwork on the walls. The condo is in the perfect location,facing ...
2 BR | 1 BA | Sleeps 3 | Quick View
Key Amenities
About this property
A beautiful historic cottage, in the complex of Sirena Blue=Blue Mermaid, located in a great area of old town Key West, within walking distance of Duval St. and beaches, available to rent for short term. Recently fully remodeled May of 2023. High end furnishings. 2 bedrooms or an office and bedroom, ...
Property Type
Key West Cottage
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
3 Bedroom 1 & half bath Historic Conch House in the Heart of Old Town Key West Queen in the Master, 1 Queen in 1st guest bedroom and 2 queen's in the 2nd guest bedroom. Nicely renovated Kitchen & Wonderful Outside Living Area with Hot Tub & Sun Deck. There is an outside shower and full ...
Property Type
Key West House
Key Amenities
About this property
Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen ...
Property Type
Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the comforts ...
Property Type
Key West Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
3 Bedroom 3 bath Partial Ocean Viewhis is the only 3 bedroom 3 bath unit in the complex. The unit is about 2000 sq feet. It will accommodate 8. 2 Master suites each with a king bed, The 3rd bedroom has 2 twin beds and there is a queen sleeper sofa in the living room. Large private balcony opens off ...
Property Type
Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. ...
Property Type
Key West House
My husband and I recently rented this home for a month and we couldn’t have enjoyed it more! Let me start with our favorite space… the backyard. From the heated pool, to the outdoor shower, guest house, ...
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master bedroom, 2 twins in the 2nd bedroom that can be converted to a King .memory foam luxury queen sleeper in the living room will comfortably accommodate your party.Watch the sunrise ...
Property Type
Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view ...
Property Type
Key West Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view. This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private ...
Property Type
Key West Condo
Key Amenities
About this property
This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms. ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer. Both bedrooms and the living room have impact doors open to your private balcony. There is a King bed in the master bedroom and a queen ...
Property Type
Key West Condo
Wanted to go to the Florida Keys, but this place popped up several times during my search. I’m so glad I chose this place. Breathe taking is the best word to use. Beautiful beach (7miles of it), nice ...
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