
Florida Keys National Marine Sanctuary Rentals
- From $414 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 $414 per night (USD)VRBO
- From $988 per night (USD)
Expedia
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)Expedia
- From $754 per night (USD)
VRBO
**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)VRBO
- From $338 per night (USD)
Expedia
**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)Expedia
- From $416 per night (USD)
VRBO
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)VRBO
- From $293 per night (USD)
Expedia
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
- 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 $293 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 $458 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 $458 per night (USD)VRBO
- From $465 per night (USD)
Expedia
**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)Expedia
- From $567 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 $567 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 $293 per night (USD)
Expedia
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)Expedia
- From $433 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 $433 per night (USD)VRBO
- From $672 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 $672 per night (USD)Expedia
- From $328 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 $328 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 $571 per night (USD)
VRBO
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 $571 per night (USD)VRBO
- From $401 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 $401 per night (USD)Expedia
- From $225 per night (USD)
VRBO
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 $225 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 $293 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 $293 per night (USD)Expedia
- From $317 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 $317 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 $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
- From $787 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 $787 per night (USD)VRBO
- From $1455 per night (USD)
Expedia
**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 $1455 per night (USD)Expedia
- From $484 per night (USD)
VRBO
Family home in gated community w/great amenities, shared pool, fitness center
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Hemingway Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $484 per night (USD)VRBO
- From $346 per night (USD)
Expedia
Sombrero Beach Villa with Private Pool and Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This beautiful villa was built in 2017, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $346 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $452 per night (USD)
Expedia
Waterfront Half-Duplex with 30-Ft. Dock, Sitting Pool, and Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Fantastic Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $452 per night (USD)Expedia
- From $119 per night (USD)
VRBO
Key Largo Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The property is located in Pirates Cove (mile marker 99 bayside), which is an early Key Largo development that is quiet ...
From $119 per night (USD)VRBO
- From $252 per night (USD)
Expedia
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Guests must register at the office unless it is after hours in which you will register at the Guard House. Unit 175 is c ...
From $252 per night (USD)Expedia
- 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 $564 per night (USD)
Expedia
208 Mariners Club Key Largo | 3 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated! This tri-level townhouse has a laid-back, welcoming Florida Keys vibe, pristine decor, sleek new kitch ...
From $564 per night (USD)Expedia
- From $483 per night (USD)
VRBO
Marina Villa Mariner`s Club 212
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Best vacation rental to explore the Florida keys. Marina Villa 212 (3b/3b) with Marina and ocean views. Escape to ...
From $483 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Fins to the Left in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy some changes in attitude and latitude in this waterfront beauty! This is a two bedroom, two bath, stilted, one-hal ...
From $385 per night (USD)Expedia
- From $482 per night (USD)
VRBO
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
You will know you're on vacation when you enter this luxurious townhome! This beautiful home is located in Kawama Yacht ...
From $482 per night (USD)VRBO
- From $999 per night (USD)
Expedia
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $999 per night (USD)Expedia
- 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 PricingVRBO
- From $243 per night (USD)
VRBO
Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to Villa Paradise – Your Monthly Retreat in the Florida Keys! Discover the ultimate Florida Keys getaway at Vill ...
From $243 per night (USD)VRBO
- From $286 per night (USD)
VRBO
House full of life with pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
House in Key Largo. Great Home for a big family, 5 bedrooms and 4 full baths. Jacuzzi. Pool (8x14') with a deck. Can bri ...
From $286 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $297 per night (USD)Expedia
- From $416 per night (USD)
VRBO
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 $416 per night (USD)VRBO
- From $463 per night (USD)
Expedia
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 $463 per night (USD)Expedia
- From $414 per night (USD)
VRBO
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 $414 per night (USD)VRBO
- From $218 per night (USD)
Expedia
Waterfront home with gorgeous patio, WiFi, gas grill, & great location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Key Colony Beach Waterfront Villa Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $218 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful Home with Great Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful home in the Florida Keys, close to everything. Amazing water views and sunrises. All Key Largo activities to e ...
Click For PricingVRBO
- From $359 per night (USD)
Expedia
water at your back door
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $359 per night (USD)Expedia
- From $568 per night (USD)
VRBO
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 $568 per night (USD)VRBO
- From $577 per night (USD)
Expedia
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 $577 per night (USD)Expedia
- From $257 per night (USD)
VRBO
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 $257 per night (USD)VRBO
- From $306 per night (USD)
Expedia
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)Expedia
- From $353 per night (USD)
VRBO
Seas the Day in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Seas the Day Modern Townhome with Swim Spa in MarathonWelcome to Seas the Day, a beautifully designed 3-bedroom, 2.5-ba ...
From $353 per night (USD)VRBO
- From $314 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 $314 per night (USD)Expedia
- From $121 per night (USD)
VRBO
A PIECE OF THE SEA,,,,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Hello! And thanks so much for your interest in our Sas-sea at sea. Also, please make sure that you've read the descripti ...
From $121 per night (USD)VRBO
- From $1181 per night (USD)
Expedia
Dog-Friendly, Oceanfront Duplex with Private Beach Access & Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beachfront Ocean Duplex Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $1181 per night (USD)Expedia
- From $302 per night (USD)
VRBO
Bright & Breezy Top Floor Ocean View Condo w/ Double Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this ...
From $302 per night (USD)VRBO
- From $579 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 $579 per night (USD)Expedia
- From $499 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 $499 per night (USD)VRBO
- From $972 per night (USD)
Expedia
Charming dog-friendly home with guest cottage & private pool - great location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $972 per night (USD)Expedia
- Click For Pricing
VRBO
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For PricingVRBO
- From $870 per night (USD)
Expedia
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Amelia House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $870 per night (USD)Expedia
- From $320 per night (USD)
VRBO
BOOK YOUR DREAM VACATION at BEACON REEF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
JANUARY just opened up, book TODAY! (Jan 2026 only 30 days 10% discount) World Famous Beacon Reef Condo (a gated commun ...
From $320 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Imagine in the Keys - Venture Out Unit 073
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine in the Keys VO073 35' Dockage Canal front 2Bd/2Ba This home features 2Bd/2Ba and is located only 3 lots from op ...
From $292 per night (USD)Expedia
- From $544 per night (USD)
VRBO
Keys Relaxing Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Have fun with the whole family at this stylish place. Explore the Florida Keys from this central location. Key Largo i ...
From $544 per night (USD)VRBO
- From $382 per night (USD)
Expedia
★Remodeled tropical delight townhome★private plunge pool close to fun activities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet -1,000m ...
From $382 per night (USD)Expedia
- From $537 per night (USD)
VRBO
**CONCH GET ENOUGH at The Truman Annex in Key West**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $537 per night (USD)VRBO
- From $4164 per night (USD)
Expedia
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis Luxury | Privacy | Iconic Location in Truman Annex Tucked away on one of the most exclusive ...
From $4164 per night (USD)Expedia
- From $1162 per night (USD)
VRBO
Boaters’ Paradise - Marlin Bay Resort & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $1162 per night (USD)VRBO
- From $287 per night (USD)
VRBO
Executive Bay Club Bayfront/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $287 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Modern 2BR Condo Old Town/Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $217 per night (USD)VRBO
- From $501 per night (USD)
Expedia
Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $501 per night (USD)Expedia
- From $410 per night (USD)
VRBO
BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your family will be close to everything when you stay at this centrally-located place. Our home is close to grocery stor ...
From $410 per night (USD)VRBO
- From $802 per night (USD)
Expedia
Balcony & Near Downtown - Sky Suite on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $802 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Palm Breeze - Villa 5030 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $279 per night (USD)VRBO
- From $1395 per night (USD)
Expedia
**ENDLESS SUMMER @ OLD TOWN** New Villa & 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! All year long ...
From $1395 per night (USD)Expedia
- From $881 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $881 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Luxury Condominium In Key Largo... Sunsets, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
From your balcony in the Kawama Tower, you get stunning vistas of ocean and palm trees. Enjoy the view from this complet ...
From $321 per night (USD)Expedia




































































































