
Florida Keys Rentals

- From $490 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 are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $490 per night (USD)VRBO
- From $720 per night (USD)
Expedia
W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lagoon!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious 4-bedroom, 3-bath home is a half a mile from the picturesque Sombrero Beach. Located on Sombrero Is ...
From $720 per night (USD)Expedia
- From $1109 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 $1109 per night (USD)VRBO
- From $660 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 $660 per night (USD)Expedia
- From $612 per night (USD)
VRBO
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $612 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 $802 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 $802 per night (USD)VRBO
- From $2840 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 $2840 per night (USD)Expedia
- From $2540 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 $2540 per night (USD)VRBO
- From $736 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 $736 per night (USD)Expedia
- From $1623 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 $1623 per night (USD)VRBO
- From $694 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 $694 per night (USD)Expedia
- From $534 per night (USD)
VRBO
Beautiful Modern House in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open layout of the living area, dining room and kitchen. Large, screened patio offers the tropical 'out of doors and fre ...
From $534 per night (USD)VRBO
- From $506 per night (USD)
Expedia
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock 3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to ...
From $506 per night (USD)Expedia
- From $488 per night (USD)
VRBO
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $488 per night (USD)VRBO
- From $313 per night (USD)
Expedia
**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 $313 per night (USD)Expedia
- From $423 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 $423 per night (USD)VRBO
- From $2124 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 $2124 per night (USD)Expedia
- From $456 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 $456 per night (USD)VRBO
- From $324 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 $324 per night (USD)Expedia
- From $452 per night (USD)
VRBO
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $452 per night (USD)VRBO
- From $1158 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 $1158 per night (USD)Expedia
- From $604 per night (USD)
VRBO
**SHANG-RI-LA @ THE BEACH** Oceanview Condo / Pool & Tennis + LAST KEY SERVICES.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $604 per night (USD)VRBO
- From $582 per night (USD)
Expedia
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $582 per night (USD)Expedia
- From $1878 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 $1878 per night (USD)VRBO
- From $394 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 $394 per night (USD)Expedia
- From $427 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 $427 per night (USD)VRBO
- From $545 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 $545 per night (USD)Expedia
- From $391 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 $391 per night (USD)VRBO
- From $1976 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 $1976 per night (USD)Expedia
- From $769 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 $769 per night (USD)VRBO
- From $972 per night (USD)
Expedia
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $972 per night (USD)Expedia
- From $856 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 $856 per night (USD)VRBO
- From $624 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 $624 per night (USD)Expedia
- From $279 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 $279 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 $237 per night (USD)
VRBO
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $237 per night (USD)VRBO
- From $695 per night (USD)
Expedia
**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 $695 per night (USD)Expedia
- From $434 per night (USD)
VRBO
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 $434 per night (USD)VRBO
- From $1444 per night (USD)
Expedia
**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 $1444 per night (USD)Expedia
- From $759 per night (USD)
VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $759 per night (USD)VRBO
- From $2111 per night (USD)
Expedia
**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 $2111 per night (USD)Expedia
- From $400 per night (USD)
VRBO
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 $400 per night (USD)VRBO
- From $675 per night (USD)
Expedia
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 $675 per night (USD)Expedia
- From $1266 per night (USD)
VRBO
4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
We offer a unique Sanctuary Villa located on the island of Duck Key. This 4 bedroom 3 bath villa sleeps 10 people comfor ...
From $1266 per night (USD)VRBO
- From $507 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 $507 per night (USD)Expedia
- From $1897 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 $1897 per night (USD)VRBO
- From $875 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 $875 per night (USD)Expedia
- From $421 per night (USD)
VRBO
Waterfront luxury Villa (30) with sunset views and boat slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $421 per night (USD)VRBO
- From $482 per night (USD)
Expedia
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $482 per night (USD)Expedia
- From $438 per night (USD)
VRBO
**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious Home & Pool + 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! OCTOPUS'S GAR ...
From $438 per night (USD)VRBO
- From $487 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 $487 per night (USD)Expedia
- From $458 per night (USD)
VRBO
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 $458 per night (USD)VRBO
- From $306 per night (USD)
Expedia
**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 $306 per night (USD)Expedia
- From $534 per night (USD)
VRBO
**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 $534 per night (USD)VRBO
- From $475 per night (USD)
Expedia
**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 $475 per night (USD)Expedia
- From $477 per night (USD)
VRBO
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 $477 per night (USD)VRBO
- From $646 per night (USD)
Expedia
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $646 per night (USD)Expedia
- From $428 per night (USD)
VRBO
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*** This property is completely renovated on the inside and out! We cordially invite you to our property and enjoy the v ...
From $428 per night (USD)VRBO
- From $333 per night (USD)
Expedia
Flamingo Nook. Renovated, Private Pool, Canal & Cabana Club Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The ultimate Florida Keys getaway! The Flamingo Nook located at Key Colony Beach near Marathon. Privacy is what separate ...
From $333 per night (USD)Expedia
- From $340 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 $340 per night (USD)VRBO
- From $960 per night (USD)
Expedia
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $960 per night (USD)Expedia
- From $202 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 $202 per night (USD)VRBO
- From $1231 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 $1231 per night (USD)Expedia
- From $1096 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 $1096 per night (USD)VRBO
- From $648 per night (USD)
Expedia
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $648 per night (USD)Expedia
- From $293 per night (USD)
VRBO
Island Therapy
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $293 per night (USD)VRBO
- From $524 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 $524 per night (USD)Expedia
- From $303 per night (USD)
VRBO
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay where you play. The spacious newly refreshed two bedroom vacation rentals are ideal for fishermen and families or ...
From $303 per night (USD)VRBO
- Click For Pricing
Expedia
4 BED DUCK KEY VILLA W/ 35FT DOCK BEHIND IT & CABANA CLUB ACCESS
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
WE HAVE JOINED CABANA CLUB IN KEY COLONY BEACH A SHORT DRIVE AWAY WHICH INCLUDES AN OLYMPIC SIZE POOL. TIKI BAR, RESTAUR ...
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- From $353 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 $353 per night (USD)VRBO
- From $295 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 $295 per night (USD)Expedia
- From $330 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 $330 per night (USD)VRBO
- From $927 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 $927 per night (USD)Expedia
- From $363 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 $363 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 $451 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 $451 per night (USD)VRBO
- From $558 per night (USD)
Expedia
Waterfront Duck Key Villa - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful and spacious 2 bedroom & 2.5 bathrooms Town house in the one and only Duck Key Florida, Harbor Village. In the ...
From $558 per night (USD)Expedia
- From $347 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 $347 per night (USD)VRBO
- From $357 per night (USD)
Expedia
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 18
Bay Harbor View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $357 per night (USD)Expedia
- From $661 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 $661 per night (USD)VRBO
- From $428 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 $428 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Headquarters Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $179 per night (USD)VRBO
- From $375 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 $375 per night (USD)Expedia
- From $326 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 $326 per night (USD)VRBO
- From $605 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 $605 per night (USD)Expedia
- From $615 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 $615 per night (USD)VRBO
- From $374 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 $374 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $324 per night (USD)VRBO
- From $325 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 $325 per night (USD)Expedia
- From $690 per night (USD)
VRBO
811 Mariners Club Key Largo | 4 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Flawless describes to the T this immaculate townhouse. Oh-so-thoughtful floor plan, exquisite decor and furnishing...top ...
From $690 per night (USD)VRBO
- From $332 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 $332 per night (USD)Expedia
- From $255 per night (USD)
VRBO
Key Largo Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Key Largo vacation in our slice of paradise. Trailer sleeps 6. Enjoy the amenities of a giant 60" television, outdoor ba ...
From $255 per night (USD)VRBO
- From $401 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 $401 per night (USD)Expedia
- From $592 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 $592 per night (USD)VRBO
- From $392 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 $392 per night (USD)Expedia
- From $678 per night (USD)
VRBO
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 $678 per night (USD)VRBO
- From $458 per night (USD)
Expedia
~ 9TH ST BEAUTIFUL HOME W/ PRIVATE POOL ON CANAL ~
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous and welcoming ground level home directly on the canal! Located in the renowned city of Key Colony Beach, Mile M ...
From $458 per night (USD)Expedia
- From $417 per night (USD)
VRBO
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Audubon House #6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $417 per night (USD)VRBO
- Click For Pricing
Expedia
PARADISE FOR BOATERS AND FISHING
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private House, 3 BR 2 BATH, CONCRETE 60 Ft dock Avaiable August 1, 2020. Boat shown in Pictures will not be there at tim ...
Click For PricingExpedia