Key West Rentals
From $447 per night (USD)VRBO
~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Home is available September 1 for a monthly rental (only). 28 night minimum** WEEKLY RENTAL: This property has a 7 n ...
From $447 per night (USD)VRBO
From $2298 per night (USD)VRBO
~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
THE PROPERTIES: With plenty of space in an ideal location, Maisons de Luxe combines a large two-story home with a stylis ...
From $2298 per night (USD)VRBO
From $1386 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 $1386 per night (USD)VRBO
From $1453 per night (USD)Expedia
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $1453 per night (USD)Expedia
From $204 per night (USD)VRBO
Key West Getaway – Island Style Living with Ocean Views & Sunrises
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $204 per night (USD)VRBO
From $625 per night (USD)Expedia
Thirsty Mermaid - Large 4/3 Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $625 per night (USD)Expedia
From $181 per night (USD)VRBO
Old Town! Spacious Condo in Historic Home w/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $181 per night (USD)VRBO
From $627 per night (USD)VRBO
Pete's East Cottage: Cypress east cottage steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $627 per night (USD)VRBO
From $1167 per night (USD)VRBO
Pete's Cottages: Twin Cypress cottages steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $1167 per night (USD)VRBO
From $478 per night (USD)VRBO
Reynolds Retreat - A Great Monthly Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Reynolds Retreat is quintessential Key West living. Located just a few blocks off Duval Street, ...
From $478 per night (USD)VRBO
From $1439 per night (USD)VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio mak ...
From $1439 per night (USD)VRBO
From $623 per night (USD)VRBO
~VISTA FRESCO~ Oceanside condominiums with resort-style amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the resort-style amenities of 1800 Atlantic Condominiums. 1800 Atlantic sits on 400 feet of oceanfront property. ...
From $623 per night (USD)VRBO
From $482 per night (USD)VRBO
Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)
- 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 $482 per night (USD)VRBO
From $941 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 $941 per night (USD)VRBO
From $819 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 $819 per night (USD)VRBO
From $495 per night (USD)Expedia
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $495 per night (USD)Expedia
From $483 per night (USD)VRBO
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $483 per night (USD)VRBO
From $895 per night (USD)VRBO
Catherine House: A charming Old Town Key West cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shoppi ...
From $895 per night (USD)VRBO
From $1107 per night (USD)VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + 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! A trip to Key ...
From $1107 per night (USD)VRBO
From $607 per night (USD)Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale 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! This ultimate ...
From $607 per night (USD)Expedia
From $632 per night (USD)VRBO
**SMOOTH SAILING @ 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 $632 per night (USD)VRBO
From $524 per night (USD)Expedia
**VILLA BAHAMA @ 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! VILLA BAHAMA ...
From $524 per night (USD)Expedia
From $920 per night (USD)VRBO
**THE CONTENTED CRANE @ 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 $920 per night (USD)VRBO
From $1850 per night (USD)Expedia
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $1850 per night (USD)Expedia
From $1731 per night (USD)VRBO
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1731 per night (USD)VRBO
From $1342 per night (USD)Expedia
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $1342 per night (USD)Expedia
From $2524 per night (USD)VRBO
**STAR OF THE SEAPORT @ OLD TOWN** Huge 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! For a truly o ...
From $2524 per night (USD)VRBO
From $775 per night (USD)Expedia
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $775 per night (USD)Expedia
From $1446 per night (USD)VRBO
Louisa House: A comfortable four bedroom vacation hideaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southe ...
From $1446 per night (USD)VRBO
From $527 per night (USD)Expedia
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / 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 $527 per night (USD)Expedia
From $557 per night (USD)VRBO
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 $557 per night (USD)VRBO
From $435 per night (USD)Expedia
Quaint, Quiet & Convenient - CasaBianca is The Perfect Old Town Sanctuary
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to CasaBianca! Here you'll find the character & charm of Old Town blended perfectly with all the modern amenitie ...
From $435 per night (USD)Expedia
From $554 per night (USD)VRBO
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $554 per night (USD)VRBO
From $1459 per night (USD)Expedia
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & 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! SOUTHERNMOST ...
From $1459 per night (USD)Expedia
From $622 per night (USD)VRBO
Our Nautical Home Key West prime location & amenities. Last minute specials.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $622 per night (USD)VRBO
From $409 per night (USD)Expedia
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Upscale islan ...
From $409 per night (USD)Expedia
From $533 per night (USD)VRBO
Poolside Breeze Retreat Key West – Your Tropical Getaway Awaits
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $533 per night (USD)VRBO
From $307 per night (USD)VRBO
South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL This bright and sunny cottage is situated on a quiet residential street. Guests can walk to the ...
From $307 per night (USD)VRBO
From $391 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 $391 per night (USD)VRBO
From $830 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 $830 per night (USD)Expedia
From $624 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 $624 per night (USD)VRBO
From $1086 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 $1086 per night (USD)Expedia
From $523 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 $523 per night (USD)VRBO
From $594 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 $594 per night (USD)Expedia
From $2467 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 $2467 per night (USD)VRBO
From $513 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 $513 per night (USD)Expedia
From $580 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 $580 per night (USD)VRBO
From $687 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 $687 per night (USD)Expedia
From $381 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 $381 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 $1032 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 $1032 per night (USD)VRBO
From $1023 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 $1023 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 $606 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 $606 per night (USD)Expedia
From $273 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 $273 per night (USD)VRBO
From $574 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 $574 per night (USD)Expedia
From $507 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 $507 per night (USD)VRBO
From $593 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 $593 per night (USD)Expedia
From $615 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 $615 per night (USD)VRBO
From $1530 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 $1530 per night (USD)VRBO
From $988 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 $988 per night (USD)VRBO
From $754 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 $754 per night (USD)Expedia
From $338 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 $338 per night (USD)VRBO
From $416 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 $416 per night (USD)Expedia
From $964 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 $964 per night (USD)VRBO
From $596 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 $596 per night (USD)Expedia
From $2011 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 $2011 per night (USD)VRBO
From $543 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 $543 per night (USD)Expedia
From $1681 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 $1681 per night (USD)VRBO
From $609 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 $609 per night (USD)Expedia
From $820 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 $820 per night (USD)VRBO
From $636 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 $636 per night (USD)Expedia
From $1294 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 $1294 per night (USD)VRBO
From $1333 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 $1333 per night (USD)Expedia
From $465 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 $465 per night (USD)VRBO
From $678 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 $678 per night (USD)Expedia
From $454 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 $454 per night (USD)VRBO
From $1404 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 $1404 per night (USD)Expedia
From $955 per night (USD)VRBO
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $955 per night (USD)VRBO
From $433 per night (USD)Expedia
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 $433 per night (USD)Expedia
From $672 per night (USD)VRBO
**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 $672 per night (USD)VRBO
From $418 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 $418 per night (USD)Expedia
From $283 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 $283 per night (USD)VRBO
From $593 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 $593 per night (USD)Expedia
From $357 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 $357 per night (USD)VRBO
From $315 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 $315 per night (USD)Expedia
From $401 per night (USD)VRBO
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 $401 per night (USD)VRBO
From $935 per night (USD)Expedia
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 $935 per night (USD)Expedia
From $439 per night (USD)VRBO
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 $439 per night (USD)VRBO
From $325 per night (USD)Expedia
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 $325 per night (USD)Expedia
From $365 per night (USD)VRBO
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 $365 per night (USD)VRBO
From $477 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 $477 per night (USD)Expedia
From $616 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 $616 per night (USD)VRBO
From $457 per night (USD)Expedia
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 $457 per night (USD)Expedia
From $293 per night (USD)VRBO
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 $293 per night (USD)VRBO
From $317 per night (USD)Expedia
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 $317 per night (USD)Expedia
From $546 per night (USD)VRBO
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)VRBO
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 $994 per night (USD)VRBO
**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 $994 per night (USD)VRBO
From $460 per night (USD)Expedia
**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 $460 per night (USD)Expedia