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From $409 per night (USD)
VRBO
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $409 per night (USD)
VRBO
From $835 per night (USD)
Expedia
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $835 per night (USD)
Expedia
From $669 per night (USD)
VRBO
Beach Club #104 - 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 $669 per night (USD)
VRBO
From $1267 per night (USD)
Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1267 per night (USD)
Expedia
From $547 per night (USD)
VRBO
**SHANG-RI-LA @ THE BEACH** Oceanview Condo / Pool & Tennis + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $547 per night (USD)
VRBO
From $592 per night (USD)
Expedia
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $592 per night (USD)
Expedia
From $2249 per night (USD)
VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2249 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $517 per night (USD)
Expedia
From $607 per night (USD)
VRBO
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SALTWATER HAR ...
From $607 per night (USD)
VRBO
From $659 per night (USD)
Expedia
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $659 per night (USD)
Expedia
From $394 per night (USD)
VRBO
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! LA PETITE PEN ...
From $394 per night (USD)
VRBO
From $1925 per night (USD)
Expedia
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $1925 per night (USD)
Expedia
From $914 per night (USD)
VRBO
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Traveling wit ...
From $914 per night (USD)
VRBO
From $971 per night (USD)
Expedia
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $971 per night (USD)
Expedia
From $586 per night (USD)
VRBO
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $586 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $436 per night (USD)
Expedia
From $275 per night (USD)
VRBO
**SUNSET POINT @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET POINT ...
From $275 per night (USD)
VRBO
From $556 per night (USD)
Expedia
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SEA CAPTAIN'S ...
From $556 per night (USD)
Expedia
From $504 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 are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $504 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $502 per night (USD)
Expedia
From $622 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $622 per night (USD)
VRBO
From $1368 per night (USD)
VRBO
Hidden away near the Southernmost Point, Louisa's Hideaway is it!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Hidden away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. ...
From $1368 per night (USD)
VRBO
From $962 per night (USD)
VRBO
Find Sanity in the Heart of Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $962 per night (USD)
VRBO
From $816 per night (USD)
Expedia
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This Old Town ...
From $816 per night (USD)
Expedia
From $302 per night (USD)
VRBO
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET DREAMS ...
From $302 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Truman Annex Gem • 2BR Condo • Walk to Beach & Bars
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 Guests Welcome to Innis-free, ou ...
From $382 per night (USD)
Expedia
From $1064 per night (USD)
VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $1064 per night (USD)
VRBO
From $494 per night (USD)
Expedia
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $494 per night (USD)
Expedia
From $1977 per night (USD)
VRBO
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1977 per night (USD)
VRBO
From $503 per night (USD)
Expedia
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $503 per night (USD)
Expedia
From $1770 per night (USD)
VRBO
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $1770 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $601 per night (USD)
Expedia
From $788 per night (USD)
VRBO
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $788 per night (USD)
VRBO
From $509 per night (USD)
Expedia
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For many, the ...
From $509 per night (USD)
Expedia
From $1423 per night (USD)
VRBO
**DIAMOND GIRL @ THE ANNEX** Elegant Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Seals & Croft ...
From $1423 per night (USD)
VRBO
From $1014 per night (USD)
Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1014 per night (USD)
Expedia
From $592 per night (USD)
VRBO
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $592 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $569 per night (USD)
Expedia
From $204 per night (USD)
VRBO
**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNDRENCHED R ...
From $204 per night (USD)
VRBO
From $1482 per night (USD)
Expedia
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $1482 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Truman Annex, two blocks from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Available for weekly, or longer, rentals (monthly or longer starting in 2026) this three-story townhouse is located on a ...
From $430 per night (USD)
VRBO
From $612 per night (USD)
Expedia
**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When you thin ...
From $612 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $371 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Dog-friendly home with pool & walk to parks & beach - snowbirds welcome
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Casa Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $419 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $364 per night (USD)
VRBO
From $578 per night (USD)
Expedia
Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cabana Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $578 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Cheery Beach Getaway Near Local Attractions - Pool & Easy Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shipyard Perch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $226 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $300 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Big Kahuna Suite 202 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $487 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Lucia Suite 201 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $357 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hemingway's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $881 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Tahiti Suite 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $419 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Conched Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $318 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $326 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Windward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $503 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $628 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Charming cottage with private hot tub - one block to Duvall Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Conch Casa Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $593 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $303 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Sunny condo with pool, lovely deck, central AC & washer/dryer - central location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Oceana Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $448 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $416 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Catalina Suite 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $320 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Elegant home with with patio & community pool - walk to beaches & Duval Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Mangrove Lagoon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $546 per night (USD)
Expedia
From $182 per night (USD)
VRBO
June & August 2026 now available! Old Town PRIVATE 3BR Lagoon Pool& FIVE stars!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This colorful three bedroom, two full bath, private, and historic home is a wonderful spot to vacation, live like a loca ...
From $182 per night (USD)
VRBO
From $846 per night (USD)
Expedia
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This modern O ...
From $846 per night (USD)
Expedia
From $477 per night (USD)
VRBO
**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 are 100% Refundable until 30 days prior to your arrival! SUZY'S PARROT ...
From $477 per night (USD)
VRBO
From $812 per night (USD)
Expedia
Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $812 per night (USD)
Expedia
From $1877 per night (USD)
VRBO
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Resembling a ...
From $1877 per night (USD)
VRBO
From $582 per night (USD)
VRBO
Bermuda Retreat-waterfront 2BR 2BA condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $582 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $251 per night (USD)
VRBO
Click For Pricing
Expedia
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $277 per night (USD)
VRBO
Boater's Dream 2Bed 2Bath Condo, 30 night stay w/ water views, balcony, pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $277 per night (USD)
VRBO
From $642 per night (USD)
VRBO
ARTIST'S CONDO @ Duval Square by Rent Key West Vacations - Located on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool a ...
From $642 per night (USD)
VRBO
From $635 per night (USD)
VRBO
Flamingo Retreat-waterfront 2BR 2BA condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $635 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $382 per night (USD)
VRBO
From $322 per night (USD)
VRBO
The Palms -3 bedroom 2 bath home in The Meadows w/ pool oasis & guest cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $322 per night (USD)
VRBO
From $633 per night (USD)
VRBO
Duval Square Retreat: A beautiful condo steps from the action
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Duval Square Retreat is In the heart of Old Town. Duval Square is located at the "artistic" and quieter end of Duval St ...
From $633 per night (USD)
VRBO
From $554 per night (USD)
VRBO
Little Paradise, Historic Harbor Old Town Key West 2/1.5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $554 per night (USD)
VRBO
From $541 per night (USD)
VRBO
Truman Annex unit 254
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $541 per night (USD)
VRBO
From $875 per night (USD)
VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $875 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
Hyatt Sunset Harbor Resort for ONLY Sunday to Sunday Week's stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is for A WEEK'S Stay Only in a 2 Bedroom 2 Bathroom Villa for 6 People. Discover this relaxing oasis in the heart ...
From $1000 per night (USD)
VRBO
From $481 per night (USD)
VRBO
Key West GULF FRONT Home with Private Dock and Heated Pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own priva ...
From $481 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Oasis in Old Town - our special home
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $267 per night (USD)
VRBO
Click For Pricing
VRBO
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For Pricing
VRBO
From $370 per night (USD)
Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $370 per night (USD)
Expedia
From $690 per night (USD)
VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $690 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Great Family Vacation Rental.
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $373 per night (USD)
Expedia
From $943 per night (USD)
VRBO
Classic Key West cottage with pool & courtyard - walk to beach & Duval St dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Papa's Hideaway - Garden of Eden Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $943 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $603 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Barts Suite 303 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $563 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $288 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Queen’s Lair Rockhouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $306 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $260 per night (USD)
Expedia
Click For Pricing
VRBO
Fresh Getaway w/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Casa Hueso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For Pricing
VRBO
From $267 per night (USD)
Expedia
Sunny Tropical Condo with WiFi & Pool - Close to Beachside Action
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Seashore at the Shipyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $267 per night (USD)
Expedia
From $116 per night (USD)
VRBO
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $116 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Bonaire Suite 210 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $258 per night (USD)
Expedia
From $3542 per night (USD)
VRBO
Multi-home tropical paradise with large, heated pool, & wraparound sundeck
Bedrooms:
6
Bathrooms:
6
Sleeps:
22
Papa's Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $3542 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Comfortable Condo with Pool, Private Balcony, & Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $540 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $593 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $144 per night (USD)
Expedia

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