Monroe Area Rentals
- From $401 per night (USD)
VRBO
High Tide awaits your next visit upgraded condo close to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a gr ...
From $401 per night (USD)VRBO
- From $1404 per night (USD)
Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1404 per night (USD)Expedia
- From $385 per night (USD)
VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! FOLLOW THE SU ...
From $385 per night (USD)VRBO
- From $1909 per night (USD)
Expedia
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $1909 per night (USD)Expedia
- From $361 per night (USD)
VRBO
Tranquility by Smathers and 10 minute bike downtown Key West value savings
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the ...
From $361 per night (USD)VRBO
- From $509 per night (USD)
Expedia
Somewhere on the Beach a dream property all amenities included simply amazing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Somewhere on the Beach has amazing views of the Atlantic Ocean and White Street Pier. The property was completely remode ...
From $509 per night (USD)Expedia
- From $799 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 $799 per night (USD)VRBO
- From $413 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 30 days prior to your arrival! For many, the ...
From $413 per night (USD)Expedia
- From $1259 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 $1259 per night (USD)VRBO
- From $764 per night (USD)
Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $764 per night (USD)Expedia
- From $377 per night (USD)
VRBO
Waterfront luxury Villa (30) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $377 per night (USD)VRBO
- From $462 per night (USD)
Expedia
**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! NATURE'S EDGE ...
From $462 per night (USD)Expedia
- From $493 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 $493 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic 4th floor condominiums unit C439. Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, tw ...
From $518 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...
From $500 per night (USD)VRBO
- From $310 per night (USD)
Expedia
**BOHEMIAN RHAPSODY @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You might ask ...
From $310 per night (USD)Expedia
- From $569 per night (USD)
VRBO
**BLUE HERON'S COVE @ THE ANNEX** Luxury Villa by Duval + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BLUE HERON'S ...
From $569 per night (USD)VRBO
- From $167 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 30 days prior to your arrival! SUNSET POINT ...
From $167 per night (USD)Expedia
- From $815 per night (USD)
VRBO
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SEA CAPTAIN'S ...
From $815 per night (USD)VRBO
- From $429 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 21 days prior to your arrival! This colorful ...
From $429 per night (USD)Expedia
- From $454 per night (USD)
VRBO
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master b ...
From $454 per night (USD)VRBO
- From $545 per night (USD)
Expedia
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! As Neptune wa ...
From $545 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Best Deals in Duck Key . 2 Bedroom \/2 Bath w\/40' 'Dock, Trailer Storage Incl,
- Bedrooms:
- 3
- 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 $313 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come relax in our Marathon Oasis...This calm, comfortable and modern updated home is a 2/2 with a great open room floor ...
From $450 per night (USD)Expedia
- From $180 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 30 days prior to your arrival! SUNDRENCHED R ...
From $180 per night (USD)VRBO
- From $345 per night (USD)
Expedia
**SOUTHERNMOST SOLACE @ OLD TOWN** Conch Cottage 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! At the Southe ...
From $345 per night (USD)Expedia
- From $1236 per night (USD)
VRBO
**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 $1236 per night (USD)VRBO
- From $631 per night (USD)
VRBO
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $631 per night (USD)VRBO
- From $220 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 $220 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Truman Annex, two blocks from Duval
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $375 per night (USD)Expedia
- From $535 per night (USD)
VRBO
**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When you thin ...
From $535 per night (USD)VRBO
- Click For Pricing
Expedia
Judy's place at Venture Out
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Judy's Place is located in the Venture Out Resort. A quiet little secret escape just 20 miles from Key West. Judy's Plac ...
Click For PricingExpedia
- From $305 per night (USD)
VRBO
Sea Bird Marina's Perfect Keys Getaway with boat slip and openwater sunset view.
- 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 $305 per night (USD)VRBO
- From $849 per night (USD)
VRBO
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 ...
From $849 per night (USD)VRBO
- From $294 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 $294 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Island-Themed, Dog-Friendly Oasis with Shared Pool & Walkable Locale
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical Village - Utopia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $273 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy Dog-Friendly Suite with WiFi, Balcony, Hot Tub, Pool, & Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Jamaica Suite 102 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
Click For PricingVRBO
- From $490 per night (USD)
Expedia
Stylish Condo with Swimming Pool - Minutes from Popular Attractions
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Truman's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $490 per night (USD)Expedia
- From $182 per night (USD)
VRBO
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 $182 per night (USD)VRBO
- From $313 per night (USD)
Expedia
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 $313 per night (USD)Expedia
- From $453 per night (USD)
VRBO
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 $453 per night (USD)VRBO
- From $334 per night (USD)
Expedia
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 $334 per night (USD)Expedia
- From $276 per night (USD)
VRBO
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 $276 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Sunny Dog-Friendly 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 $270 per night (USD)Expedia
- From $196 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 $196 per night (USD)VRBO
- From $529 per night (USD)
Expedia
Colorful condo with deck & balcony - near downtown & beaches
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Cubana at Duval Square R14 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $529 per night (USD)Expedia
- From $188 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 $188 per night (USD)VRBO
- From $2319 per night (USD)
Expedia
Six Dog-Friendly Homes in Quiet Neighborhood with Private Pool & Hot Tub
- Bedrooms:
- 9
- Bathrooms:
- 12
- Sleeps:
- 34
Tropical Village Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $2319 per night (USD)Expedia
- From $268 per night (USD)
VRBO
Condo in Historic District with Shared Hot Tub - Two Blocks to Ocean, Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Duval Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $268 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Waterfront Duck Key Villa - Sleeps 6
- Bedrooms:
- 3
- 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 $504 per night (USD)Expedia
- From $549 per night (USD)
VRBO
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hemingway's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $549 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Flamingo Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $266 per night (USD)Expedia
- From $266 per night (USD)
VRBO
Updated Corner Condo with Pool, Hot Tub, WiFi, Covered Parking - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Sea Breeze Suite 101 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $266 per night (USD)VRBO
- From $266 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 $266 per night (USD)Expedia
- From $171 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 $171 per night (USD)VRBO
- From $298 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 $298 per night (USD)Expedia
- From $304 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 $304 per night (USD)VRBO
- From $412 per night (USD)
Expedia
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $412 per night (USD)Expedia
- From $1040 per night (USD)
VRBO
Dog-Friendly Home with Patio and Private Hot Tub - Walk to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Southernmost Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $1040 per night (USD)VRBO
- From $427 per night (USD)
Expedia
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 $427 per night (USD)Expedia
- From $247 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 $247 per night (USD)VRBO
- From $237 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 $237 per night (USD)Expedia
- From $643 per night (USD)
VRBO
Flawless! 811 Mariners Club Key Largo
- 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 $643 per night (USD)VRBO
- From $493 per night (USD)
Expedia
5 O’clock Paradise - Beautiful 3 bedroom, 3 bath home w\/private Pool.
- 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 $493 per night (USD)Expedia
- From $70 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 $70 per night (USD)VRBO
- From $226 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 $226 per night (USD)Expedia
- From $264 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 $264 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Elegant home with with patio & community pool - walk to beaches & Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Mangrove Lagoon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $385 per night (USD)Expedia
- From $349 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 $349 per night (USD)VRBO
- From $712 per night (USD)
Expedia
Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breeze ...
From $712 per night (USD)Expedia
- From $315 per night (USD)
VRBO
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES.
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is t ...
From $315 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
- From $1263 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 $1263 per night (USD)VRBO
- From $654 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 $654 per night (USD)Expedia
- From $434 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 $434 per night (USD)VRBO
- From $475 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 $475 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Dog-friendly home w\/ large private pool only a short walk to Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $256 per night (USD)VRBO
- From $192 per night (USD)
Expedia
Comfortable Waterfront Vacation Rental
- 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 $192 per night (USD)Expedia
- From $315 per night (USD)
VRBO
Little Paradise, Historic Harbor Old Town Key West 2\/2
- Bedrooms:
- 2
- 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 $315 per night (USD)VRBO
- From $599 per night (USD)
Expedia
Island Life! 208 Mariners Club Key Largo
- 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 $599 per night (USD)Expedia
- From $890 per night (USD)
VRBO
VILLA MARINA IN MARINER'S CLUB KEY LARGO - RENOVATED 2019 BEST NEW LISTING
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Luxurious Villa remodeled in 2019 in the exclusive Mariner's Club of Key Largo, Florida. This property has Marina, Atla ...
From $890 per night (USD)VRBO
- From $410 per night (USD)
Expedia
Vacation Home on Open Gulf with Fantastic Panoramic View
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Our home in Marathon at M.M.51, is located in a tropical setting on the open gulf surrounded by lush palms. Marathon is ...
From $410 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Fins to the Left 2 bed 2 bath Duplex w\/ Cabana Club & dockage
- 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 $338 per night (USD)VRBO
- From $587 per night (USD)
Expedia
Townhome w\/saltwater lagoon views, 2 pools, ocean access, tennis courts, 3br\/3ba
- 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 $587 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Waterfront Half-Duplex with 30-Ft. Dock, Sitting Pool, and Private Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Fantastic Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $324 per night (USD)VRBO
- From $130 per night (USD)
Expedia
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 $130 per night (USD)Expedia
- Click For Pricing
VRBO
Gated Vacation Oasis Luxury Home Sunset Point Key Largo
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to a one of a kind gated vacation oasis and experience the relaxing breezes of the bay from every room and around ...
Click For PricingVRBO
- From $221 per night (USD)
Expedia
Key Colony Beach Now booking for 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This unit is perfect for snowbirds seeking a fabulous winter retreat for fishing boating and other activities as well ...
From $221 per night (USD)Expedia
- From $879 per night (USD)
VRBO
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 5
- Bathrooms:
- 4
- 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 $879 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $215 per night (USD)
VRBO
Villa Paradise: 4 bed\/2 bath canalfront home with new dock on the way!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Villa Paradise is the perfect home base for your Florida Keys adventure. Just four canals in from the ocean on Ramrod Ke ...
From $215 per night (USD)VRBO
- From $887 per night (USD)
Expedia
Wonderful 4 Bedroom 4 bathroom waterfront estate!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to "Casa Luna", a 4 bedroom 4 bathroom estate 3 are master bedrooms with bathrooms. You can enjoy the roof top j ...
From $887 per night (USD)Expedia
- From $250 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 $250 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $250 per night (USD)Expedia
- From $275 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 $275 per night (USD)VRBO
- From $220 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 $220 per night (USD)Expedia
- From $330 per night (USD)
VRBO
Great Family Vacation Rental.
- Bedrooms:
- 3
- 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 $330 per night (USD)VRBO
- From $55 per night (USD)
Expedia
Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $55 per night (USD)Expedia
- From $340 per night (USD)
VRBO
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 $340 per night (USD)VRBO
- From $258 per night (USD)
Expedia
Stylish Dog-Friendly Condo with Balcony - In Heart of the Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kingfish Keep On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $258 per night (USD)Expedia