Key West Rentals
From $203 per night (USD)HomeAway
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $203 per night (USD)HomeAway
From $200 per night (USD)VRBO
Shipyard Palms: A first floor condo in the Shipyard of Truman Annex
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard C ...
From $200 per night (USD)VRBO
From $150 per night (USD)HomeAway
Truman Annex Unit 177
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Hemingway's Cottage is the first floor of a two story town home in the award winning private gated community Truman Anne ...
From $150 per night (USD)HomeAway
From $500 per night (USD)VRBO
Flower Power House ~ Sleeps 12+ Good Value with Giant Pool in Key West
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key ...
From $500 per night (USD)VRBO
From $250 per night (USD)HomeAway
Casa Cayo Hueso in old town Key West 3 bedroom 2 bath with hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Cayo Hueso, which means “Key West House”, is a perfect example of shotgun architecture with a front porch and back ...
From $250 per night (USD)HomeAway
From $130 per night (USD)VRBO
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nice quiet vacation landing a few blocks from the action on Duval Street. This Saturday-Saturday home in Key West has: - ...
From $130 per night (USD)VRBO
From $425 per night (USD)HomeAway
Craig & Cindy's Key West Truman Annex Porter House (4 bedroom with private pool)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $425 per night (USD)HomeAway
From $350 per night (USD)VRBO
Enjoy private pool and Old Town location at TROPICAL DREAMING, PET FRIENDLY!
- Bedrooms:
- 4.5
- Bathrooms:
- 2
- Sleeps:
- 6
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and c ...
From $350 per night (USD)VRBO
From $70 per night (USD)HomeAway
Heart of Old Town, Truman Annex Beautiful, Large, 1st Flr, 2BR KING/twins, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! Come and see what's special about the S ...
From $70 per night (USD)HomeAway
From $130 per night (USD)VRBO
Namaste 'the spirit within me salutes the spirit within you'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $130 per night (USD)VRBO
From $349 per night (USD)HomeAway
Charming Key West Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
True Key West flavor! - move in ready. 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on ...
From $349 per night (USD)HomeAway
From $334 per night (USD)VRBO
Paradise on the Golf
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical 2-story conch style townhome recently renovated and newly furnished located in the Key West Golf Club Resort. ...
From $334 per night (USD)VRBO
From $125 per night (USD)HomeAway
Steps To The Beach And The Sunrise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnis ...
From $125 per night (USD)HomeAway
From $250 per night (USD)VRBO
Bottom's Up Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfection in the Meadows awaits you in a pristine Florida Bungalow. This two bedroom, two bathroom home offers all the ...
From $250 per night (USD)VRBO
From $500 per night (USD)HomeAway
Royal Palms Estate Key West
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Experience Key West in style at this one of a kind luxury home. Royal Palms Estate is an exquisite 5 bedroom/ 6 bathroom ...
From $500 per night (USD)HomeAway
From $200 per night (USD)VRBO
One bedroom, two bath, sleeps 2 - Monthly Rental- AVAILABLE FOR JANUARY
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy and comfortable home will transition you from the hustle and bustle of your everyday life to the relaxing hist ...
From $200 per night (USD)VRBO
From $450 per night (USD)HomeAway
Stunning Victorian-Caribbean Estate in Key West Historic Seaport Neighborhood
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $450 per night (USD)HomeAway
From $214 per night (USD)VRBO
Craig & Cindy Key West Truman Annex 212 Fleming House
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
We are Craig & Cindy and we thank you for inquiring about our Truman Annex Key West vacation homes. Truman Annex is ide ...
From $214 per night (USD)VRBO
From $485 per night (USD)HomeAway
~ SOUTHARD COMFORT ~ Historic Home w/ Heated Pool, Parking & Quiet Location!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: “Southard Comfort” is true Island living in Historic "Old Town" Key West. Nancy & Carl welcome yo ...
From $485 per night (USD)HomeAway
From $350 per night (USD)VRBO
Duval Square Courtyard Condo is just steps from the action
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includ ...
From $350 per night (USD)VRBO
From $152 per night (USD)HomeAway
King size bed, Truman Annex location, CITY CAY
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman ...
From $152 per night (USD)HomeAway
From $275 per night (USD)VRBO
Beach Club #103 - Unique oceanfront living with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $275 per night (USD)VRBO
From $178 per night (USD)HomeAway
Key West home w/shared pool and just steps from historic Old Town
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Bright Key West Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $178 per night (USD)HomeAway
From $315 per night (USD)VRBO
~FAIR WINDS @ THE FOUNDRY~ Updated Townhome w/ Pool, Close To Ft Zach Beach!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: Fair Winds at the Foundry is a gorgeous coastal 3 story, 2 bedroom, 2.5 bath immaculate light and ...
From $315 per night (USD)VRBO
From $414 per night (USD)HomeAway
Key West Oasis, Seperate Cottage, Very Private Pool & Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $414 per night (USD)HomeAway
From $450 per night (USD)VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $450 per night (USD)VRBO
From $55 per night (USD)HomeAway
Hollinsed House Poolside / King Studio / sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $55 per night (USD)HomeAway
From $180 per night (USD)VRBO
~LEMONADE MERMAID~ Dog-Friendly, Heated POOL, Fenced Yard. Off street parking
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: You’re going to delight being in Lemonade Mermaid! This adorable gingerbread cottage with amazing ...
From $180 per night (USD)VRBO
From $159 per night (USD)HomeAway
~ MY HAPPY PLACE ~ Tropical Home w/ Private Pool In Heart of 'Old Town' KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: My Happy Place is an exemplary renovation of an historic, Key West house. It retains its original ...
From $159 per night (USD)HomeAway
From $380 per night (USD)VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming conch cottage has gone through some wonderful changes in 2019! Enter the private courtyard of the home, t ...
From $380 per night (USD)VRBO
From $99 per night (USD)HomeAway
Luxury 2/2 condo In Heart Of Key West With Lagoon Pool. Monthly rentals only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our luxury condo is one of four prestigious units which comprise this beautiful, two-story, plantation style building. F ...
From $99 per night (USD)HomeAway
From $240 per night (USD)VRBO
Cuban Club Suites - 2 Bed/2 Bath - Shared Pool - Sleeps up to 8- Summer Rates
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Built in 1917 as a 'club' for Cuban cigar makers and their families as their 'home away from home', it soon became the c ...
From $240 per night (USD)VRBO
From $150 per night (USD)HomeAway
Bonus!!! Two bicycles provided! Beautifully appointed first floor condo.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Complex The Truman Annex is truly one of a kind in Key West. It is a gated community with impeccably kept grounds. ...
From $150 per night (USD)HomeAway
From $520 per night (USD)VRBO
The Pavilion Villa ~ A Private Paradise in Downtown Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $520 per night (USD)VRBO
From $388 per night (USD)HomeAway
~ CASABLANCA GRANDE ~ 2 'Old Town' Cottages w/ Pvt Pool, Hot Tub, & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: Casablanca Grande consists of the two neighboring vacation rentals "Casablanca" & "Casablanca Too" ...
From $388 per night (USD)HomeAway
From $467 per night (USD)VRBO
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Imagine your whole group staying in one home, with each couple in their own private bedroom suite. At CASA SUITE CASA i ...
From $467 per night (USD)VRBO
From $59 per night (USD)HomeAway
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...
From $59 per night (USD)HomeAway
From $357 per night (USD)VRBO
WATERFRONT LUXURY HOME WITH VIEW & PRIVATE HEATED POOL
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $357 per night (USD)VRBO
From $207 per night (USD)HomeAway
Rooster Haven @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $207 per night (USD)HomeAway
From $322 per night (USD)VRBO
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sometimes in life a 'stroke of good fortune' leads you to discover something so delightful at a moment when you're not e ...
From $322 per night (USD)VRBO
From $207 per night (USD)HomeAway
Almost Paradise @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $207 per night (USD)HomeAway
From $614 per night (USD)VRBO
Catch of the Day @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 7
View passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former ...
From $614 per night (USD)VRBO
From $436 per night (USD)HomeAway
**THE TOASTED COCONUT @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Throughout Key West you'll find subtle touches of coconuts; from the towering coconut palms nestled throughout the stree ...
From $436 per night (USD)HomeAway
From $545 per night (USD)VRBO
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
All year long you dream of a getaway to capture that feeling of Key West's endless summer - carefree days spent tooling ...
From $545 per night (USD)VRBO
From $400 per night (USD)HomeAway
@ Forever ocean front views expansive 3 bedroom key west condo@
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breeze ...
From $400 per night (USD)HomeAway
From $171 per night (USD)VRBO
Sand Crab Cabana @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $171 per night (USD)VRBO
From $250 per night (USD)HomeAway
205E La Brisa - 2 Bedroom Oceanfront Condo with a Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $250 per night (USD)HomeAway
From $200 per night (USD)VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described a ...
From $200 per night (USD)VRBO
From $327 per night (USD)HomeAway
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This modern Old Town condo is designed for the real downtown experience in the Conch Republic. VILLA ANGELITA is located ...
From $327 per night (USD)HomeAway
From $545 per night (USD)VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? ...
From $545 per night (USD)VRBO
From $257 per night (USD)HomeAway
Green Bamboo @ the Truman Annex
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Paradise! This 2 bedroom townhouse, one bedroom is a king and the second bedroom features twin beds which can ...
From $257 per night (USD)HomeAway
From $251 per night (USD)VRBO
CONCH COTTAGE -Old Town Location - WEEKLY vacation rental - Hot Tub - 1BD/1BA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO CONCH COTTAGE! In the 20th century many residents of Key West began referring to themselves as “Conchs”, now ...
From $251 per night (USD)VRBO
From $291 per night (USD)HomeAway
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
While Old Town Key West has its fair share of impressive homes, few can compare to ENVY OF THE ISLAND a freshly built tw ...
From $291 per night (USD)HomeAway
From $531 per night (USD)VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 8
Like many of the highlights of Key West, THE ADMIRAL'S ESTATE celebrates a rich history of the island while embracing a ...
From $531 per night (USD)VRBO
From $550 per night (USD)HomeAway
**COASTAL CABANA @ LOVE LANE** Cul-de-Sac Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
Located only two blocks from Duval Street and the Historic Seaport is a truly spectacular Old Town Key West home that ex ...
From $550 per night (USD)HomeAway
From $45 per night (USD)VRBO
Superb Location, Affordably Priced
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key ...
From $45 per night (USD)VRBO
From $184 per night (USD)HomeAway
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $184 per night (USD)HomeAway
From $240 per night (USD)VRBO
@ New Owners, Enchanting garden view on the Ocean Last minute discounts @
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper ...
From $240 per night (USD)VRBO
From $400 per night (USD)HomeAway
Pelican Landing St. Kitts Penthouse
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $400 per night (USD)HomeAway
From $279 per night (USD)VRBO
Amberjack @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $279 per night (USD)VRBO
From $171 per night (USD)HomeAway
Seagull Lull @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $171 per night (USD)HomeAway
From $294 per night (USD)VRBO
**CIELO AZUL @ THE BEACH CLUB** Oceanfront Condo / Pools + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This freshly renovated oceanfront condo has been meticulously designed and furnished to a very high standard. No expense ...
From $294 per night (USD)VRBO
From $446 per night (USD)HomeAway
**THE POLYNESIAN HOUSE @ CASA MARINA** Estate & Huge Pool + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
THE POLYNESIAN HOUSE" is an extraordinarily unique and whimsical home, designed to capture the culture and experience of ...
From $446 per night (USD)HomeAway
From $240 per night (USD)VRBO
Poolside Breeze Retreat A103: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the poo ...
From $240 per night (USD)VRBO
From $150 per night (USD)HomeAway
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $150 per night (USD)HomeAway
From $338 per night (USD)VRBO
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! Check out this unique 5 Bedroom Key West Vacation Rental – Island Time- with separate histori ...
From $338 per night (USD)VRBO
From $79 per night (USD)HomeAway
Villa Soleil at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Soleil in luxurious surroundings. Renovated in 2017 it has a fully equipped kitchen with dining area. Th ...
From $79 per night (USD)HomeAway
From $185 per night (USD)VRBO
Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located only two miles from Duval 1800 Atlantic Blvd offers the best of both worlds; close to downtown without most of t ...
From $185 per night (USD)VRBO
From $340 per night (USD)HomeAway
Ocean Extravaganza C438: 2 BR, 2 BA Condominium in Key West, Sleeps 5
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Two Bedroom Premiere Ocean View This is a beautiful top floor two bedroom ocean-view unit at 1800 Atlantic. You cannot ...
From $340 per night (USD)HomeAway
From $763 per night (USD)VRBO
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 12
CASA VICTORIA, located in the heart of Old Town just two blocks from Duval Street, is a large 5 bedroom home built with ...
From $763 per night (USD)VRBO
From $257 per night (USD)HomeAway
Ivory Coast in the Truman Annex*
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 6
This stately 2 bedroom end-unit townhouse in the President's Walk area of Porter Lane is furnished with tropical and lux ...
From $257 per night (USD)HomeAway
From $273 per night (USD)VRBO
**2 COOL FISH @ THE ANNEX** Chic Villa + Pool + LAST KEY SERVICES…
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
2 COOL FISH is a fashionable 2-story townhome located in Truman Annex, a gated community located in the heart of Old Tow ...
From $273 per night (USD)VRBO
From $207 per night (USD)HomeAway
Manatee @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $207 per night (USD)HomeAway
From $250 per night (USD)VRBO
Beautiful Old Town Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Old Town, this historic house has a wonderful floor plan, high ceilings and beautiful Dade County pine walls. ...
From $250 per night (USD)VRBO
From $378 per night (USD)HomeAway
JASMINE PLACE - 1 blk to Duval - Private Pool - Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO JASMINE PLACE! Jasmine Place is a beautiful and enchanting home conveniently located next door to the Ernest ...
From $378 per night (USD)HomeAway
From $251 per night (USD)VRBO
**VILLA MODERNA @ CASA MARINA** Sleek Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Straight out of the pages of a magazine, this exquisite vacation home offers an experience like no other in Key West. VI ...
From $251 per night (USD)VRBO
From $83 per night (USD)HomeAway
It's a Salt Life After All @ the Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...
From $83 per night (USD)HomeAway
From $215 per night (USD)VRBO
37 ft. Economy Boat In The REAL Downtown Key West Economy Sailboat Spring 2020
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
This is the REAL Key West Experience since 1995. February through April is our busy season. Spring Break is filling in ...
From $215 per night (USD)VRBO
From $429 per night (USD)HomeAway
Historic, cozy, prime location with amazing pool and garden in Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a little piece of Key West Paradise? Well, this is it! This stunning cottage is only steps away from the His ...
From $429 per night (USD)HomeAway
From $695 per night (USD)VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...
From $695 per night (USD)VRBO
From $171 per night (USD)HomeAway
A Pleasant Stay @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $171 per night (USD)HomeAway
From $274 per night (USD)VRBO
Top Floor Ocean Views from every window Newly Renovated for 2020
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Paradise Found hes been renovated for 2020 and beyond. New Master Bathroom, Reconfigured Master Bedroom and Rem ...
From $274 per night (USD)VRBO
From $571 per night (USD)HomeAway
A Sunset Breeze @ the Truman Annex
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $571 per night (USD)HomeAway
From $170 per night (USD)VRBO
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
SUZY'S PARROT PERCH is a charming apartment that is located in the heart of Old Town on the corner of two historic stree ...
From $170 per night (USD)VRBO
From $300 per night (USD)HomeAway
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desi ...
From $300 per night (USD)HomeAway
From $1363 per night (USD)VRBO
**AVALYNN HOUSE @ THE ANNEX** Lush Home by Beach & Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 8
Imagine being just a few minutes walk from all of Key West's most famous attractions, yet in the peace and solitude of K ...
From $1363 per night (USD)VRBO
From $236 per night (USD)HomeAway
Gracie Bay's Hideaway @ The Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Thank you for considering Gracie Bay’s Hideaway for your escape to the tropical paradise of Key West. Here you will enjo ...
From $236 per night (USD)HomeAway
From $600 per night (USD)VRBO
"STARS AND STRIPES" ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $600 per night (USD)VRBO
From $117 per night (USD)HomeAway
30 night Minimum Stay Heart of Historic downtown 214 2 bed 2 1/2 Bath
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps ...
From $117 per night (USD)HomeAway
From $281 per night (USD)VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Upscale island living is epitomized with this beautiful home, CAYO CALYPSO. This modern home is well appointed, spacious ...
From $281 per night (USD)VRBO
From $279 per night (USD)HomeAway
Archipelago l @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $279 per night (USD)HomeAway
From $300 per night (USD)VRBO
Casa Colonial Island Luxury Historic Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful Casa Colonial is a luxury island residence in the heart of the historic district with a wonderful island desig ...
From $300 per night (USD)VRBO
From $250 per night (USD)HomeAway
BAYA HOUSE -Old Town WEEKLY Vacation Rental - Shared Pool - 2BD/2BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO BAYA HOUSE! The Baya House is a lovely 'Conch Style' Key West Vacation home. Conveniently located just a b ...
From $250 per night (USD)HomeAway
From $300 per night (USD)VRBO
NEW UNIT!!! GORGEOUS!!Island Oasis @ Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. The living area is the entir ...
From $300 per night (USD)VRBO
From $405 per night (USD)HomeAway
Tiki BeachToo! Truman Annex. Just 2 blocks to Duval, pool, grill, bicycle,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tiki Beach Too is a Newly Renovated, 2 bedroom/2bathroom, charming town home in enchanting Truman Annex, in the heart of ...
From $405 per night (USD)HomeAway
From $150 per night (USD)VRBO
28 night minimum stay. 3 Bedroom House with a pool in Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key We ...
From $150 per night (USD)VRBO
From $104 per night (USD)HomeAway
Coconut: 2 BR / 1 BA private home in Key West, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $104 per night (USD)HomeAway
From $218 per night (USD)VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This colorful two story Old Town cottage is just right for a delightful stay in the Conch Republic. VILLA CUBANA is loca ...
From $218 per night (USD)VRBO
From $209 per night (USD)TripAdvisor
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacati ...
From $209 per night (USD)TripAdvisor
From $165 per night (USD)PerfectPlaces
Osprey
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West ha ...
From $165 per night (USD)PerfectPlaces