Showing

PreviousNext property

$183

3 BR / 3 BA / Sleeps 6

3 Reviews

$183

Inquire

South Street Serentiy-Great Location, Private Pool, Parking, Steps to the Beach

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

This light and airy 3 bedroom, 2.5 bath home has a wrap around deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private gate and you will be in a tropical paradise, surrounded by lush palms, fiery bougainvillea, and tropical ambiance. Here you can be part of the …
  • Internet Access
  • Grill
  • Linens Provided
  • Towels Provided
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Best location, great rental for families~

Left on Apr 29, 2014 for a stay in January 2014

We loved the location, walking distance to everything. The house had everything you could need. There was confusion on the temperature of the pool, which wasn't discovered for nearly two weeks into the rental month, but was quickly readjusted. There were a few leaks that must be repaired by now, as the management company responded quickly. It was quiet and in a nice neighborhood with respectful …

PreviousNext property

$133

2 BR / 2 BA / Sleeps 6

30 night minimum stay requirement.  2 Bedroom 2 Bathroom Condo with Beautiful - Key West vacation rentals
1 / 14

$133

Inquire

30 night minimum stay requirement. 2 Bedroom 2 Bathroom Condo with Beautiful

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

30- Night minimum stay: Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Beautifully decorated with palm tree décor, leather sleeper sofa, warm colors to give …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$127

2 BR / 2 BA / Sleeps 4

2 Reviews

$127

Inquire

Angela Cottage: A hideaway in Old Town

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows create a relaxing Key …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Outstanding

Left on Jun 26, 2009 for a stay in March 2009

I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and outdoor dining area is outstanding for any meal. The kitchen is new and all the necessary pots and pans are present.

PreviousNext property

$193

3 BR / 4 BA / Sleeps 6

2 Reviews

$193

Inquire

Packer Retreat: A beautifully renovated "Conch" house

Key West house
3 BR / 4 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden area. Nicely decorated …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great house needs updating

Left on Jun 18, 2009 for a stay in February 2009

Packer retreat is a great house. So great I am renting it in 2010. The layout and outdoor space is unusually large for Key West. And the home is very private and quiet. the location is within walking distance to Duval and White streets.

The home is beautifully decorated but needs to be "freshened" up. The sofas and carpets are dirty. the kitchen has very little equipment (1 pan, no serving…

PreviousNext property

$93

1 BR / 1 BA / Sleeps 2

The Treetop Apartment at the Sailmaker`s House Sleeps 2 Historic Old Town - Key West vacation rentals
1 / 35

$93

Inquire

The Treetop Apartment at the Sailmaker`s House Sleeps 2 Historic Old Town

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Gorgeous one bedroom apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. One bedroom one bath floor plan maximizes the space in this airy tree top apartment. Comfortable Queen …
  • Internet Access
  • A/C or climate control
  • Parking
  • Linens Provided
  • Microwave
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$113

2 BR / 2 BA / Sleeps 6

Mango Menagerie:  A treasury of island colors and Key West charm - Key West vacation rentals
1 / 17

$113

Inquire

Mango Menagerie: A treasury of island colors and Key West charm

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

30 DAY MINIMUM RENTAL Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite Flaming Buoy restaurant. The property is …
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$173

3 BR / 2 BA / Sleeps 6

3 Reviews

$173

Inquire

Elizabeth Retreat: A three bedroom historic home in Old Town

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 3 Reviews

Details

Reviews

(3)

30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly restored eyebrow 3 …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

A month in Key West

Left on Jun 18, 2009 for a stay in January 2009

We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful - really stayed on top of everything and went out of their way to accomodate our schedule on check in and check out. The house was absolutely lovely and clearly well cared for. We liked it so much, we are coming back …

PreviousNext property

$83

1 BR / 1 BA / Sleeps 2

1 Reviews

$83

Inquire

Southard Square Hideaway Old Town, Pool, Parking Too!

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic Key West, you will be only 4 blocks from world famous Duval Street and 3 blocks away from the scenic Historic Seaport of Key West. Please see our video!! When you arrive, park your car in your dedicated parking …
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great location...Relax and enjoy!

Left on Apr 27, 2014 for a stay in January 2014

Very nice condo with huge pool area. Very clean and neat. We loved the location! We would love to go back again some day. The only negative was the living room furniture. It seem really inexpensive and quite uncomfortable...it did looked nice. No table in condo...only counter with two small bar stools. Wish it had a small table with 4 chairs. Condo manager Carlos was wonderful.

PreviousNext property

$490

3 BR / 3 BA / Sleeps 6

6 Reviews

$490

Inquire

Sleeps up to 6: Southard Comfort Historic Old Town Private Pool

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

“Southard Comfort”, True Island Living in Downtown Historic Old Town Key West Two story, 3 bedroom, 2.5 bath plus outdoor shower. Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of excellence. …
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Grill
  • Microwave
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Fiftieth Bday Party

Left on Oct 13, 2014 for a stay in June 2014

Fantastic house and location! Three couples and we all have been to EYW annually over the last 25 years...we have rented almost every large home in EYW and this is one of the best! Great spot,nice pool kitchen was really bigger than needed...outdoor shower is always a favorite and off street parking for a rental car or in our case six bikes....

Would definitely return to this house....

PreviousNext property

$208

2 BR / 1 BA / Sleeps 4

1 / 25

$208

Book

TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St.

Key West cottage
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people watching, it's all…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$418

3 BR / 4 BA / Sleeps 8

1 / 34

$418

Book

"ALEXANDRIA'S SECRET" Luxurious Home w/ Private Pool - 1/2 Block to Duval St

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view

Details

Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost city has to offer- …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

Book

GRAND TURK SUITE #404 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$418

3 BR / 3 BA / Sleeps 8

1 / 30

$418

Book

"A KEY ESCAPE"- Luxury Vacation Rental w/ Private Pool- 1/2 Block To Duval St

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and stainless steel …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$270

2 BR / 1 BA / Sleeps 4

43 Reviews

$270

Inquire

Key Lime Calypso: A cottage in the heart of Bahama Village

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 43 Reviews

Details

Reviews

(43)

The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this two bedroom cottage…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(43)

Lovely cottage and great location

Left on Jun 18, 2009 for a stay in September 2008

The cottage was a great "get away from it", but yet was right in the heart of the main area Key West, just off Duval St. As the property was centrally located along Duval St, it was also quiet and peaceful. The private pool was great to have and the garden had a lovely sunny aspect, but there was enough shade to get out of the sun if you wanted too. The pool was welcome as the main beaches on the…

PreviousNext property

$83

2 BR / 2 BA / Sleeps 2

1 / 10

$83

Inquire

Minimum 90 day rental - 1 bedroom 1 Bathroom Condo at Las Salinas

Key West condo
2 BR / 2 BA / Sleeps 2 | Quick view

Details

Minimum 90 day stay requirement- Las Salinas is well maintained and has a beautiful community pool. Offers covered parking. There is a shared swimming pool.Located in New Town featuring 1 bedroom with a queen sized bed and one bathroom. The unit has a private balcony and offers covered parking. There is a shared …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$167

3 BR / 3 BA / Sleeps 8

1 / 19

$167

Inquire

30 night minimum stay requirement. Waterfront Escape - 3 Bedroom House on Ca

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Located in Big Coppitt is this secluded, waterfront paradise. This 3 bedroom, 3 bathroom house features a private pool. Relax in the grand outdoor patio area overlooking the pool and canal. Each of the three bedrooms has its own private bathroom. Located on the ground floor is the living room, dining area, kitchen and…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$167

3 BR / 2 BA / Sleeps 8

1 / 16

$167

Inquire

30 night minimum stay requirement. The Palms - 3 Bedroom House with a Swimmi

Key West house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area is in between the …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$133

2 BR / 2 BA / Sleeps 4

1 / 11

$133

Inquire

30 night minimum stay requirement. The Pearl in Paradise - 2 Bedroom House w

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely remodeled with hardwood …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$795

3 BR / 3 BA / Sleeps 6

1 / 28

$795

Inquire

Cloud 9-Private Pool - 1/2 Block from Duval - Five Star Luxury - Parking

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find yourself in the private brick courtyard facing the home with its French doors and balconies. As …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$150

2 BR / 2 BA / Sleeps 4

1 / 19

$150

Inquire

Smuggler`s Den | Live outdoors this summer | Perfect for four

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

History buffs love to immerse themselves in the centuries old legends of Key West – and if they’re lucky, they’ll find room in Smuggler’s Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the island. Smuggler’s Den, a …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$310

2 BR / 1 BA / Sleeps 4

1 / 11

$310

Inquire

Luxury 2 Bedroom Suite: HARRY

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses with premium linens, …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$245

1 BR / 1 BA / Sleeps 2

1 / 12

$245

Inquire

Luxury 1 Bedroom Suite - Newly renovated and immaculate!

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view

Details

THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses with premium linens, …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$310

2 BR / 1 BA / Sleeps 4

1 / 12

$310

Inquire

Luxury 2 Bedroom Suite

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses with premium linens, …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$100

1 BR / 1 BA / Sleeps 2

1 / 15

$100

Inquire

Poppy | Summer special | Perfect cottage for two

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. From the moment you step up onto the front porch, which is perfect for people watching, and into the open …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$245

1 BR / 1 BA / Sleeps 2

1 / 12

$245

Inquire

Luxury 1 Bedroom Suite

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view

Details

THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses with premium linens, …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$267

4 BR / 3 BA / Sleeps 7

1 / 28

$267

Inquire

Southard Love | Porches and pool | Summer dreams

Key West house
4 BR / 3 BA / Sleeps 7 | Quick view

Details

SOUTHARD LOVE Simply tell your friends and family to meet you at the corner of Southard Street and Love Lane, one of Key West’s premier Old Town addresses. This spectacular, three-story, historic and award-winning home has been fully renovated to meet the most discerning tastes. Dappled sunlight plays across the…
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$275

3 BR / 3 BA / Sleeps 8

10 Reviews

$275

Inquire

Island Days - Fishing, Boating, Golfing, Dining, Shopping!

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

The Best of Everything! "Island Days" has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping, off street parking steps to your door, all in a private 3 bedroom 3 bathroom town house located in the gated Coral Hammock community just a few minutes from Old Town Key …
  • Grill
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(10)

Our fabulous stay at Island Days in Key West

Left on Oct 26, 2013 for a stay in June 2013

I wanted to take my sons and future daughter in-law and her two children to Key West for a week vacation this past summer and had been searching on line for a house or townhouse/condo to rent for our stay. After 1 place falling through I came upon Island Days townhouses. I have to say that it was everything and more! It was decorated beautifully and was exactly as the photos shown! It made me …

PreviousNext property

$127

2 BR / 2 BA / Sleeps 4

1 / 11

$127

Inquire

South Street Cottage: Bright & sunny in the Casa Marina district

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

30 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights, light tile floors and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$179

2 BR / 3 BA / Sleeps 4

2 Reviews

$179

Inquire

Olivia Cottage: A charming Old Town house near Key West's historic cemetery

Key West house
2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our town, the Oliva …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Stepping Into a Picture

Left on Jul 21, 2011 for a stay in June 2011

I stayed in Olivia Cottage five weeks and loved every minute. After looking at pictures on the internet, I felt like I was stepping into the pictures. It's exactly as shown. The patio/pool area is just the most relaxing place. Everything I needed was provided and the staff at KW Vacation Rentals were most friendly and helpful. I had one problem with the smoke detectors and it was repaired quickly…

PreviousNext property

$215

1 BR / 1 BA / Sleeps 2

1 / 24

$215

Inquire

Casa Alegre

Key West villa
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Nestled midway between the Atlantic Ocean and the Gulf of Mexico is Casa Alegre, an easy-living one-bedroom, one-bath duplex cottage featuring a bubbling hot tub on its own private deck. The White Street corridor is an Old Town neighborhood unto itself, yet the world-famous Duval Street in easy walking distance. In …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$700

3 BR / 3 BA / Sleeps 7

1 Reviews

$700

Inquire

Secret Villa II Newly Listed and Available - Sleeps 6 - Private Pool - Parking

Key West house
3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

We are excited to announce the owner of our most popular luxury vacation rental "SECRET VILLA" is now offering the mirror image as a vacation rental! Available NOW...."SECRET VILLA II"! Location, Location, Location....This amazing property is situated on a quiet and peaceful lane away from traffic and noise. The …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wedding moon with friends

Left on Jan 18, 2015 for a stay in January 2015

Made a long weekend with friends even better. This place is in a great location just a block or two off Duvall street. The house is outstanding and has a great private heated pool. Also has a great little porch and court yard for mornings and evenings for a drink or two. The house has two nice bedrooms upstairs with private baths and one downstairs with its own bath. Great place to visit with …

PreviousNext property

$600

2 BR / 2 BA / Sleeps 6

1 / 24

$600

Inquire

Garden Home Paradise in Midtown Key West

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered outdoor pavillion with …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$110

1 BR / 2 BA / Sleeps 2

2 Reviews

$110

Inquire

Newton Street Hideaway: A secluded one bedroom

Key West house
1 BR / 2 BA / Sleeps 2 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale for an extended stay …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

A Second Home

Left on Jun 17, 2011 for a stay in May 2011

We have stayed at the Newton Street Hideaway for several years, and, as soon as we open the door, it's just like coming home! It's fun to spot the improvements made by the owners since our previous visit (this time there were new rugs in the kitchen, and stools at the breakfast bar) The house is situated in the quiet residential area known as The Meadows, on the far side of White Street, but it …

PreviousNext property

$83

1 BR / 1 BA / Sleeps 2

2 Reviews

$83

Inquire

The Studio at the Sailmaker`s House Sleeps 2 Historic Old Town

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. The open concept floor plan maximizes the space in this airy tree top studio. Comfortable Queen size bed will…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Linens Provided
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

great place, great location, great stay!

Left on Sep 02, 2014 for a stay in July 2014

I really enjoyed my stay at the sailmaker's studio. The staff as well as the owner were very easy to work with and very helpful. My small dog was with me and he enjoyed it too. It is just blocks away from the wharf and restaurants, shops, grocery stores, sailing/boating trips are also just short walks away. It has all the typical amenities you could want: 2 balconies (1 is shared with another apt…

PreviousNext property

$290

2 BR / 2 BA / Sleeps 5

14 Reviews

$290

Inquire

Beach Club #204 - Unique Oceanfront living

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 14 Reviews

Details

Reviews

(14)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This is one of the most elegant and colorful 2 bedroom units in the Key West Beach Club. It …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(14)

Great Time

Left on Jun 18, 2009 for a stay in May 2008

I just wish I had the money to buy a condo at The Beach Club. It's the second time I've stayed there and each time was perfect.

PreviousNext property

$173

3 BR / 4 BA / Sleeps 8

3 Reviews

$173

Inquire

Casa Alegria - a Bahamian style conch house

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park bicycles. You can park…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

paradise

Left on Apr 24, 2014 for a stay in January 2014

We were fortunate enough to stay in this immaculate and welcoming retreat. We loved swimming in the pool and riding the bikes around town. We could not have asked for a more perfect place to make our vacation more fabulous!!!! Love...love...love!

PreviousNext property

$490

4 BR / 4 BA / Sleeps 8

40 Reviews

$490

Inquire

Louisa House: A comfortable four bedroom vacation hideaway

Key West house
4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 40 Reviews

Details

Reviews

(40)

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(40)

Great House, Family Friendly

Left on Jun 18, 2009 for a stay in April 2009

This is the second time I have stayed at this house and we have loved it both times. The house is within walking distance to everything we needed and wanted to do and offered many amentities. The pool area is very nice and the house is very spacious. The only downfall is I wish the pool area had more than 2 lounge chairs and that the trees were cut back a little more so some sunshine could …

PreviousNext property

$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

Book

CAT ISLAND SUITE #205 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Terrible ” 1 Reviews

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Aweful

Left on Nov 11, 2014 for a stay in October 2014

Avoid this place at all costs . It is horrible ….. I would rather have stayed in my car. The apartment was disgusting . Furniture looked like it was from the early 80's and was dirty.

The walls are mirrored and broken, fixed with tape. The smoke alarms are missing but the wires are hanging out of the walls. I would never stay there again. I do have to say the girl at the front desk was nice …

PreviousNext property

$220

0 BR / 1 BA / Sleeps 2

43 Reviews

$220

Inquire

Bali Hideaway: A studio cottage that's perfect for two

Key West cottage
0 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 43 Reviews

Details

Reviews

(43)

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(43)

great place for two!

Left on Jun 18, 2009 for a stay in July 2007

You don't know your only a block off the "main drag". No noise; serene and absolutely beautiful grounds made our stay better than a condo I rented a couple of years before. Absolutely loved the place!!

PreviousNext property

$743

3 BR / 4 BA / Sleeps 8

1 / 25

$743

Inquire

Ocean Paradise

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view

Details

Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing available as well. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$133

2 BR / 2 BA / Sleeps 6

8 Reviews

$133

Inquire

Casa Manana 2 bedroom Cottage in Old Town Key West

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from Faustos grocery, Sandy…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(8)

Perfect Location

Left on Sep 10, 2010 for a stay in June 2010

We visited Key West with another couple for a week in June. We were extremely please with the charming home we stayed in. Has everything you could possible need. Perfect location, minutes from Duval Street, was great we walked everywhere. We plan on coming back next year and hope to rent the home again. Thanks all Florida Keys for making our stay so memorable!

PreviousNext property

$175

3 BR / 2 BA / Sleeps 8

1 / 16

$175

Inquire

Island Elegance ~ Near The Beach ~ Monthly Rental

Key West house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous…
  • Housekeeping Optional
  • A/C or climate control
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$240

1 BR / 1 BA / Sleeps 2

48 Reviews

$240

Inquire

Ann Street Tranquility: A cozy and peaceful cottage

Key West cottage
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 48 Reviews

Details

Reviews

(48)

This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(48)

Ann Street

Left on Jun 18, 2009 for a stay in May 2007

We enjoyed the cottage. The interior was beautiful and very clean. Very nicely decorated with higher end accessories. The location was absolutely perfect. The only improvement that could be made was the entrance and pool area was not well manicured. It was very overgrown and jungle like. We would not hesitate to return.

PreviousNext property

$150

4 BR / 3 BA / Sleeps 8

1 Reviews

$150

Inquire

Large 4 Bedroom W/ Pool! `Seabreeze` Luxury Vacation Rental in the Sanctuary

Key West house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the "Sanctuary" on the Key West Golf Club. Key West Golf Club legend Rees Jones masterfully designed this 18 hole, 6500 yard course to be a challenge to players of all abilities. …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Awesome Month!!!

Left on May 01, 2014 for a stay in February 2014

We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the pool. [the pool company not sweeping the pool} a lot of vegetation so many leaves and such in pool. Gym [we were told it was included and they tried charging us, took a few days to get key] But, I will say everything worked …

PreviousNext property

$220

1 BR / 1 BA / Sleeps 4

49 Reviews

$220

Inquire

Colony Poolside: A charming bungalow near the historic cemetery

Key West cabin
1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 49 Reviews

Details

Reviews

(49)

Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a nice private deck …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(49)

Disappointing

Left on Jun 18, 2009 for a stay in February 2008

After viewing pictures of this cottage on line I was impressed with the layout, decor and proximity to the pool. So, I was looking forward to our stay there.
Disappointed is the only word I can use to describe how I felt when we arrived and actually saw this space in person.
The pool area and the surrounding grounds were not maintained.
The deck patio furniture was filthy and the deck itself …

PreviousNext property

$370

3 BR / 2 BA / Sleeps 6

42 Reviews

$370

Inquire

Whitehead House: A unique two story home beside the Audubon House

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 42 Reviews

Details

Reviews

(42)

Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1 space). An outdoor …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(42)

Hidden Jewel

Left on Jun 18, 2009 for a stay in July 2008

This house is fantastic! The location is awesome - right in the middle of everything!!! Everything you would want was there. House was clean, pool was excellent and off street parking is great! The 2 bedrooms and bathroom downstairs are small, but for the amount of time you really need them, they are fine. I would certainly recommend this house and plan to rent it again.

PreviousNext property

$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

Inquire

Beach Club #104 - Unique oceanfront living with breathtaking views

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining area and master …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

Good facility overall, but lots of rules for teeneagers

Left on Apr 16, 2011 for a stay in March 2011

Beach Club #104 is nicely and recently decorated. Everything was in good working order (TVs, washer/dryer, kitchen appliances). The cleaning service could have done a better job. There are a number of loose floor tiles which could be dangerous for older renters. The public areas are well kept, but there are some rather draconian rules -- the owners are not particularly friendly and I have to …

PreviousNext property

$450

3 BR / 3 BA / Sleeps 6

35 Reviews

$450

Inquire

Villa Paradiso: A unique mid-town paradise

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 35 Reviews

Details

Reviews

(35)

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavillion with an ornate…
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(35)

The 3 couples loved this home.

Left on Jun 18, 2009 for a stay in February 2009

We chose the Villa because it advertised 3 bedrooms and 3 baths. I would advertise it as 2.5 bedrooms. However, the space worked out very well for the 6 of us. The home is graciously appointed and easy to live in. The small pool area was a perfect gathering spot. There were other decks and seating areas when each of us choses a bit more privacy. The Villa was within walking distance of the …

PreviousNext property

$240

1 BR / 2 BA / Sleeps 2

47 Reviews

$240

Inquire

Ann Street Cottage: A bright and airy home near Duval Street

Key West cottage
1 BR / 2 BA / Sleeps 2 | Quick view
“ Excellent ” 47 Reviews

Details

Reviews

(47)

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(47)

Nice

Left on Jun 18, 2009 for a stay in July 2006

My husband and I stayed at the ann street cottage. It is a nice cozy house. Nice size bedroom, and a equipped kitchen to make your own dinners. We went shopping for groceries and made a nice dinner every night--saved a ton on eating out. The cottage was quiet, and clean--there is also a nice private outdoor back patio area. There is also a nice community pool. Only drawback was that the tv …

PreviousNext property

$100

2 BR / 1 BA / Sleeps 4

1 / 28

$100

Inquire

Angelfish Cottage | Summer slow lane | Bring a friend or two

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Historic Old Town Classic Conch Cottage This monthly vacation home is located in the heart of Historic Old Town Key West Florida on a very private, quiet lane. Restaurants & bars, marinas and shopping are all within walking distance. 6 blocks from the center of Duval St. and 6 blocks from the historic seaport. Your …
  • Internet Access
  • A/C or climate control
  • Parking
  • Grill
  • Linens Provided
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 23456
page 1 of 9
Load more