Key West Rentals
From $150 per night (USD)HomeAway
Cool Breeze @ the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...
From $150 per night (USD)HomeAway
From $233 per night (USD)VRBO
A Bella Capri @ the Beach
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $233 per night (USD)VRBO
From $207 per night (USD)HomeAway
Tropical Breezes @ 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 $208 per night (USD)VRBO
Sail Boat Catamaran / House Boat/ Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
As you starting reading about my boat, I would like to tell you what we doing to protect traveling public from Covid-1 ...
From $208 per night (USD)VRBO
From $100 per night (USD)HomeAway
Truman Annex Condo, Close to Beach & Duval with 2 Bikes, Upper level, Free WIFI!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the Beautiful Shipyard of ...
From $100 per night (USD)HomeAway
From $271 per night (USD)VRBO
Alegre @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in picturesque Truman Annex in fabulous, sunny Key West, Alegre is close to all the fun and activities yet quiet ...
From $271 per night (USD)VRBO
From $171 per night (USD)HomeAway
Oyster's Pearl @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $171 per night (USD)HomeAway
From $125 per night (USD)VRBO
@Free Island Spirit Key West March 2020 $5500 Monthly plus fees @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
From $125 per night (USD)VRBO
From $343 per night (USD)HomeAway
Forever Young @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $343 per night (USD)HomeAway
From $207 per night (USD)VRBO
About Time @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $207 per night (USD)VRBO
From $414 per night (USD)HomeAway
Aqua Breeze @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $414 per night (USD)HomeAway
From $714 per night (USD)VRBO
"SOUTHERNMOST BELLE"~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $714 per night (USD)VRBO
From $327 per night (USD)HomeAway
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $327 per night (USD)HomeAway
From $89 per night (USD)VRBO
Downtown, Affordable & Clean available Winter of 2021- Extended stay discount
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $89 per night (USD)VRBO
From $268 per night (USD)HomeAway
@ Amazing Ocean Front 3 Bedroom Open Winter of 2022 @
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride ...
From $268 per night (USD)HomeAway
From $234 per night (USD)VRBO
Peaceful Setting Amongst The Active Island Life Style
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlan ...
From $234 per night (USD)VRBO
From $236 per night (USD)HomeAway
A Sunset Poolside @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $236 per night (USD)HomeAway
From $218 per night (USD)VRBO
**SOUTHERN STAR @ THE MEADOWS** 4BR Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)VRBO
From $171 per night (USD)HomeAway
SPECTACULAR PRICE :) Tropical Vineyard @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
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 $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Andros
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)VRBO
From $207 per night (USD)HomeAway
Blue Heaven @ 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 $872 per night (USD)VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $872 per night (USD)VRBO
From $175 per night (USD)HomeAway
Beach Chic w a Waterfront Park View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please call or text if you’d like to book our home 702 232... 3750 When booking our home please include a brief descri ...
From $175 per night (USD)HomeAway
From $487 per night (USD)VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $487 per night (USD)VRBO
From $643 per night (USD)HomeAway
!!LADY EMMA!! BEAUTY!! VERY PRIVATE!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Lady Emma which is located in the best location in Old Town, the world famous Truman Annex on Emma St. The Tr ...
From $643 per night (USD)HomeAway
From $189 per night (USD)VRBO
**HEART of the HARBOR @ THE SEAPORT** Old Town Living & Pool + LAST KEY SERVICES
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $189 per night (USD)VRBO
From $436 per night (USD)HomeAway
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
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
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $545 per night (USD)VRBO
From $171 per night (USD)HomeAway
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)HomeAway
From $200 per night (USD)VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
A few words about the 'damn'pandemic… The health and safety of our guests and employees is our top priority. Our homes ...
From $200 per night (USD)VRBO
From $545 per night (USD)HomeAway
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $545 per night (USD)HomeAway
From $257 per night (USD)VRBO
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)VRBO
From $349 per night (USD)HomeAway
KEY WEST LIVIN' Beautiful 50' Yacht with 3 Bed, 2 Bath sleeps 6.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SAFER THEN ANY HOTEL IN KEY WEST PRIVATE AND SECLUDED ACCOMMODATION. We are The safest option for travel to Key West ...
From $349 per night (USD)HomeAway
From $291 per night (USD)VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $291 per night (USD)VRBO
From $531 per night (USD)HomeAway
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $531 per night (USD)HomeAway
From $550 per night (USD)VRBO
**COASTAL CABANA @ LOVE LANE** Cul-de-Sac Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $550 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
Fall Specials Enchanting garden view on the Ocean Great Rates @@
- 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 $279 per night (USD)HomeAway
Amberjack @ the Truman Annex
- Bedrooms:
- 2
- 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)HomeAway
From $294 per night (USD)VRBO
**CIELO AZUL @ THE BEACH CLUB** Oceanfront Condo / Pools + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
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
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
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
Click For PricingHomeAway
PEAK OF DUVAL: Sophisticated Bright & Breezy Duval Street Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
Click For PricingHomeAway
From $545 per night (USD)VRBO
"STRIPES" ~ Delightful Condo Located in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $545 per night (USD)VRBO
From $273 per night (USD)HomeAway
**2 COOL FISH @ THE ANNEX** Chic Villa + Pool + LAST KEY SERVICES…
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $273 per night (USD)HomeAway
From $207 per night (USD)VRBO
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)VRBO
From $150 per night (USD)HomeAway
Closer to Cuba than Walmart - Blu
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This nightly rental i ...
From $150 per night (USD)HomeAway
From $995 per night (USD)VRBO
"SEAHORSE COVE" ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $995 per night (USD)VRBO
From $467 per night (USD)HomeAway
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $467 per night (USD)HomeAway
From $59 per night (USD)VRBO
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)VRBO
From $322 per night (USD)HomeAway
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $322 per night (USD)HomeAway
From $207 per night (USD)VRBO
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)VRBO
From $614 per night (USD)HomeAway
Catch of the Day @ the Truman Annex
- Bedrooms:
- 2
- 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)HomeAway
Click For PricingVRBO
Discounted April spacious 2 BR second floor apartment in historic Conch home!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful large 2 bedroom, 1 bath second floor apartment with high ceilings and beautifully decorated. Near beaches and ...
Click For PricingVRBO
Click For PricingHomeAway
LAST MINUTE OFFER! 44' Sailing Yacht & Other Boats
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
You will have this one of a kind, yacht all to yourself! This yacht has a large great room and kitchen area with window ...
Click For PricingHomeAway
From $171 per night (USD)VRBO
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)VRBO
From $571 per night (USD)HomeAway
Beautiful Large home!
- Bedrooms:
- 2
- 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 $345 per night (USD)VRBO
"OFF CALL" ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
GATED COMMUNITY CLOSE TO BOATING AND GOLFING... “OFF CALL” is a beautiful townhome in the Coral Hammock community; total ...
From $345 per night (USD)VRBO
From $170 per night (USD)HomeAway
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $170 per night (USD)HomeAway
From $300 per night (USD)VRBO
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $300 per night (USD)VRBO
From $1363 per night (USD)HomeAway
**AVALYNN HOUSE @ THE ANNEX** Lush Home by Beach & Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $1363 per night (USD)HomeAway
From $236 per night (USD)VRBO
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)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
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $281 per night (USD)VRBO
From $279 per night (USD)HomeAway
Archipelago l @ the Truman Annex
- Bedrooms:
- 2
- 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 $228 per night (USD)VRBO
"CASA DE VINO" ~ Amazing Price for Charming Townhouse with Pool & Tiki!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Casa de Vino, in the Coral Hammock Community is a gorgeous three bedroo ...
From $228 per night (USD)VRBO
From $300 per night (USD)HomeAway
NEW UNIT!!! GORGEOUS!! Island Oasis @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $300 per night (USD)HomeAway
From $405 per night (USD)VRBO
Tiki BeachToo! 2 blocks to Duval, pool, grill, bikes
- 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)VRBO
From $104 per night (USD)HomeAway
**COCONUT** Old Town! Adorable!
- 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
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)VRBO
From $218 per night (USD)HomeAway
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)HomeAway
From $382 per night (USD)VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $382 per night (USD)VRBO
From $507 per night (USD)HomeAway
"LADY ADMIRAL" ~ Sweet cottage & guest house with private pool off Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $507 per night (USD)HomeAway
From $1095 per night (USD)HomeAway
"SPARROW'S LANDING" ~ Casual Sophistication Located in a Quiet Neighborhood!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
STEP INTO PARADISE... Located in the peaceful neighborhood locals call The Meadows, this home is set away from the noise ...
From $1095 per night (USD)HomeAway
From $50 per night (USD)VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)VRBO
From $240 per night (USD)HomeAway
Charming Home in Old Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise on Pine, a monthly rental, is a picture perfect home that sits high above this lovely one way street with an i ...
From $240 per night (USD)HomeAway
From $300 per night (USD)VRBO
Special Rates For Both Weekly And Monthly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Foundry are Bostonian style, 3 level townhouses that have been refurbished with tropical flair. Vaulted ceilings gre ...
From $300 per night (USD)VRBO
From $174 per night (USD)HomeAway
**HERE COMES THE SUN @ CASA MARINA** Home / Large Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $174 per night (USD)HomeAway
From $284 per night (USD)VRBO
SPECIAL PRICING May 2021 "OCEAN FRONT! 90 FT BALCONY-Spectacular View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". (CFAR) CSA Insurance In the even ...
From $284 per night (USD)VRBO
From $50 per night (USD)HomeAway
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)HomeAway
From $491 per night (USD)VRBO
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $491 per night (USD)VRBO
From $343 per night (USD)HomeAway
Above it All in Mills Place @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
IMMACULATE RETREAT STEPS FROM IT updated and redecorated, this beautifully designed and appointed Truman Annex multi-le ...
From $343 per night (USD)HomeAway
From $167 per night (USD)VRBO
30 night minimum stay requirement. Key Haven Retreat - 4 Bedroom House with
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your wate ...
From $167 per night (USD)VRBO
From $80 per night (USD)HomeAway
A Palm Tree Paradise @ the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $80 per night (USD)HomeAway
From $500 per night (USD)VRBO
4 bd w/loft Condo w/ boat slip Pelican Landing St Croix
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
St. Croix Penthouse (for 12 people) features four bedrooms and four private baths. The master bedroom has a king bed, on ...
From $500 per night (USD)VRBO
Click For PricingHomeAway
Portside Villa⚓️☀️🐬
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Portside Villa, a multi-million dollar old town treasure Vacation Townhouse for rent by the month Welcome to the most ...
Click For PricingHomeAway
From $279 per night (USD)VRBO
Pelican's Perch @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $279 per night (USD)VRBO
From $90 per night (USD)HomeAway
Luxurious Historic House With Pool in Old Town INTRODUCTORY RATES!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...
From $90 per night (USD)HomeAway
From $202 per night (USD)VRBO
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $202 per night (USD)VRBO
From $80 per night (USD)HomeAway
Beauty on the Green at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beauty on the Green --2 BDRM/1.5 BA townhome with easy access to the front pool.*****PLEASE NOTE THIS IS A MONTHLY RENTA ...
From $80 per night (USD)HomeAway
From $75 per night (USD)VRBO
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 4
Two newly renovated studios sleeps 4 guests.complete with ,linens, flat screen TV, cable, Wi-Fi and kitchenettes/storage ...
From $75 per night (USD)VRBO
From $107 per night (USD)HomeAway
Parrots Perch B415: 2 BR, 2 BA Condominium in Key West, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $107 per night (USD)HomeAway
From $218 per night (USD)VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)VRBO
From $350 per night (USD)HomeAway
"SEAS THE DAY"~ Newly Built Townhome in Perfect Location with Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
IMMACULATE RETREAT JUST STEPS FROM IT ALL... Beautifully designed and decorated townhouse located in the Southernmost Ca ...
From $350 per night (USD)HomeAway
From $414 per night (USD)VRBO
Ocean Breeze @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $414 per night (USD)VRBO
From $209 per night (USD)HomeAway
PARADISE IN OLD TOWN!!!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to a beautiful house, hidden paradise, you never knew existed. Once you're entered into this hideaway, you'll ne ...
From $209 per night (USD)HomeAway
From $425 per night (USD)VRBO
Dreamworks Conch Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $425 per night (USD)VRBO
From $207 per night (USD)HomeAway
Green Spot @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $207 per night (USD)HomeAway
From $188 per night (USD)VRBO
CORAZON Old Town MONTHLY vacation rental - Private Pool - LARGE 2BD/2.5BA
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO CORAZON! We are complying with the directives listed on the Monroe County website. Please be aware that inf ...
From $188 per night (USD)VRBO
From $207 per night (USD)HomeAway
Havana Views @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $207 per night (USD)HomeAway
Click For PricingVRBO
Spotless Fully Renovated Family Home. Free parking WiFi Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in ...
Click For PricingVRBO
From $175 per night (USD)HomeAway
Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
'The Plantation' is a 3 bed 3 bath townhome located within the gated community of Truman Annex in Key West's Old Town ar ...
From $175 per night (USD)HomeAway
From $203 per night (USD)VRBO
Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perche ...
From $203 per night (USD)VRBO
From $325 per night (USD)HomeAway
Classic Pet-friendly 3/2 in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming conch home is uniquely located on a corner property across the street from The Studios of Key West, in the ...
From $325 per night (USD)HomeAway
From $125 per night (USD)VRBO
"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $125 per night (USD)VRBO
From $100 per night (USD)HomeAway
Studio overlooking historic Key West waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $100 per night (USD)HomeAway
From $160 per night (USD)VRBO
LAVENDER JUNGLE Whimsical Vibe, Large Outdoor Space, Shared Pool, Walk to All
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West' ...
From $160 per night (USD)VRBO
From $200 per night (USD)HomeAway
2 bedroom 2.5 bath town home in Old town Key West- Monthly Rental only
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
A CUT ABOVE II in OLD TOWN-PARK@YOUR DOOR Even though this is a 29 day rental-you can get together with friends or famil ...
From $200 per night (USD)HomeAway
From $2059 per night (USD)VRBO
Seaport Treasure Estate
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
An exceptional degree of creativity is displayed in this detailed renovation that artfully intertwines 3 dwellings: two ...
From $2059 per night (USD)VRBO
From $395 per night (USD)HomeAway
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $395 per night (USD)HomeAway
From $240 per night (USD)VRBO
~ STEAMPLANT #211 ~ World Class Luxury Condo w/ Amazing Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 211! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $180 per night (USD)HomeAway
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $180 per night (USD)HomeAway
From $449 per night (USD)VRBO
Down Island Digs ~ Downtown with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $449 per night (USD)VRBO
From $700 per night (USD)HomeAway
CASA GRANDE - Entertainers Dream, Great for Families and Events, Private Pool
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 12
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and clo ...
From $700 per night (USD)HomeAway
From $198 per night (USD)VRBO
~ BOHEMIAN HOUSE ~ Newly Renovated "Old Town" Home w/ Pvt Pool. Pets OK!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: The Bohemian House is a restored historic home full of delightful surprises! This home is placed on the N ...
From $198 per night (USD)VRBO
From $325 per night (USD)HomeAway
200 feet from Duval Street, but quiet and secluded
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Villas is a small, historic property located 200 feet from Duval Street. This is gorgeous two bedroom, two bat ...
From $325 per night (USD)HomeAway
From $409 per night (USD)VRBO
30% OFF 2021 28 nts PRKING FREE Ft Zach BCH PASS/ COMM POOL
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
I will send you a special offer with the additional discount -30% OFF any month in 2021....Old Town -Whitehead St- BEST ...
From $409 per night (USD)VRBO
From $100 per night (USD)HomeAway
Beautifully restored 2 bed apartment in historic Old Town neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood r ...
From $100 per night (USD)HomeAway
From $275 per night (USD)VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 201 ...
From $275 per night (USD)VRBO
From $240 per night (USD)HomeAway
~ THE STEAMPLANT 210 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 210! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)HomeAway
From $185 per night (USD)VRBO
Orange Blossom Suite - Nightly rental one half block off World Famous Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to sweet paradise! Located at 510 Petronia, the 'Orange Blossom Suite' is in close proximity to all the fun-fill ...
From $185 per night (USD)VRBO
From $132 per night (USD)HomeAway
Old Town Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly redecorated by a one of Key West top interior designers!! Elegant and adorable cottage on one of the nicest lanes ...
From $132 per night (USD)HomeAway
From $80 per night (USD)VRBO
Atlantis House's Master Suite... voted top 25 in USA - Steps from beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Atlantis House the most private and unique Guesthouse in Key West with only 2 rooms, private entrances and se ...
From $80 per night (USD)VRBO
From $174 per night (USD)HomeAway
HANDS DOWN THE BEST DEAL IN KEY WEST
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $174 per night (USD)HomeAway
From $175 per night (USD)VRBO
Clean and Relaxing!! 3 King Suites!! Home with everything you need
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home in Key West has been fully updated with new furnishings. It is located in the upscale Coral Hammoc ...
From $175 per night (USD)VRBO
From $85 per night (USD)HomeAway
Club Cuba Suite at Top of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)HomeAway
From $250 per night (USD)VRBO
Charming Craftsman Home in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy one of the most vibrant locations that Key West has to offer. The tropics meet historic craftsman charm at this ir ...
From $250 per night (USD)VRBO
From $357 per night (USD)HomeAway
Luxury Tropical Villa
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The best of both worlds! This 4BR/5BA beautifully furnished luxury home features covered off-street parking, lush tropic ...
From $357 per night (USD)HomeAway
From $163 per night (USD)VRBO
~ MARTHA TRUMAN SUITE ~ Luxury Suite w/ Spacious Sundeck & Plunge Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Book your stay in the Martha Truman Suite, a lovely 1 bed, 1 bath luxury suite located on the 2nd floor of ...
From $163 per night (USD)VRBO
From $325 per night (USD)HomeAway
Downtown Cottage in Historic District-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Cottage Atocha offers 2 bedrooms, living room with orginia ...
From $325 per night (USD)HomeAway
From $310 per night (USD)VRBO
Salacia- Luxury 2/2 Ocean-front condo- Gated Key West Beach Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Imagine enjoying morning coffee, an afternoon cocktail or an evening meal of stone crabs on a spacious and comfy third-f ...
From $310 per night (USD)VRBO
From $130 per night (USD)HomeAway
"Tranquility " at Ann Street Gardens Steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $130 per night (USD)HomeAway
From $207 per night (USD)VRBO
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 baths)
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $207 per night (USD)VRBO
From $225 per night (USD)HomeAway
Luxurious monthly rental in mid-town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day minimum Rental: Tucked away behind a contemporary privacy fence and an attractive cobblestoned driveway is this h ...
From $225 per night (USD)HomeAway
From $329 per night (USD)VRBO
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $329 per night (USD)VRBO
Click For PricingHomeAway
Vacation Rental in Coral Hammock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home wi ...
Click For PricingHomeAway
From $1000 per night (USD)VRBO
Private Home with Sun-filled Pool-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Backyard pool offers lots of sunshine. This home sits in Key Lime Grove Subdivision which I was born and raised in. It ...
From $1000 per night (USD)VRBO
From $140 per night (USD)HomeAway
~ COPA CABANA ~ Cute Conch Home w/ Pvt Pool In "Old Town." Live Like A Local!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: Open the door to Key West’s past when you arrive at Copa Cabana, a quaint, 1923 “shotgun” house that was o ...
From $140 per night (USD)HomeAway
From $200 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $200 per night (USD)VRBO
From $578 per night (USD)HomeAway
~ Chick-A-Pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Chick-A-Pea is a traditional Key West cottage that has undergone a complete renovation. The charm and hist ...
From $578 per night (USD)HomeAway
Click For PricingVRBO
Havana Moon over Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Open the front door of the hand crafted Havana Moon Key West cottage located on Upper Duval Street, step from the porch, ...
Click For PricingVRBO
From $265 per night (USD)HomeAway
Bonaire Suite- A beautiful Island Retreat- Shared Pool- Gated compound
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 6
Bonaire Suite is bi-level suite with 2 queen beds upstairs separated by a privacy curtain and a queen sofa bed in the li ...
From $265 per night (USD)HomeAway
From $275 per night (USD)VRBO
OCEANFRONT ECSTASY - KW Beach Club #304
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. “Beach Club #304” is a serene waterfr ...
From $275 per night (USD)VRBO
Click For PricingHomeAway
Key West Oceanfront Resort with private sandy beach, 1BR, 1BA
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This is a 1BR, 1BA condo in small private a Key West timeshare complex. It is located on a private sandy beach. Coconut ...
Click For PricingHomeAway
From $214 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $214 per night (USD)VRBO
From $85 per night (USD)HomeAway
Key Lime Pie Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)HomeAway
From $325 per night (USD)VRBO
Island Hideway Minutes From Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Higgs Beach Hideaway offers all the amenities for a long term stay in Key West. This tropical home features 3 bedrooms w ...
From $325 per night (USD)VRBO
Click For PricingHomeAway
CHRISTMAS WEEK IN KEY WEST COCONUT MALLORY RESORT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
DELUXE 2 BEDROOM CONDO This is a 2 bedroom, 2 bathroom condo unit that features a full kitchen and a flat panel televisi ...
Click For PricingHomeAway
From $957 per night (USD)VRBO
~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL. Dogs OK!
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
THE PROPERTY and BED CONFIGURATIONS: GRAND MAISON (the Main House) is located in the Gallery District right on Duval Str ...
From $957 per night (USD)VRBO
Click For PricingHomeAway
KEY WEST - Weekly Stay Only - 2 Bedroom 2 Bathrooms Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Coconut Mallory Marina and Resort is located in the southernmost city in the continental United States. Key West, Fl ...
Click For PricingHomeAway
From $325 per night (USD)VRBO
Downtown Cottage just off famous Duval Street-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $325 per night (USD)VRBO