Monroe Area Rentals
From $519 per night (USD)VRBO
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $519 per night (USD)VRBO
From $635 per night (USD)Expedia
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 $635 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 $1140 per night (USD)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 ...
From $1140 per night (USD)Expedia
From $403 per night (USD)VRBO
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $403 per night (USD)VRBO
From $527 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 $527 per night (USD)Expedia
From $561 per night (USD)VRBO
Dog-friendly condo with pool, hot tub, balcony, central AC, W\/D, & fitness room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Saint Lucia Suite 201 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $561 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $389 per night (USD)VRBO
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 18
Bay Harbor View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $389 per night (USD)VRBO
Click For PricingExpedia
Condo in Historic District with Shared Hot Tub - Two Blocks to Ocean, Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
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From $412 per night (USD)VRBO
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 $412 per night (USD)VRBO
From $766 per night (USD)Expedia
**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 $766 per night (USD)Expedia
From $695 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 $695 per night (USD)VRBO
From $538 per night (USD)Expedia
Updated Corner Condo with Pool, Hot Tub, WiFi, Covered Parking - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Sea Breeze Suite 101 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $538 per night (USD)Expedia
From $560 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 $560 per night (USD)VRBO
From $586 per night (USD)Expedia
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 $586 per night (USD)Expedia
From $716 per night (USD)VRBO
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $716 per night (USD)VRBO
From $2382 per night (USD)Expedia
Dog-Friendly Home with Patio and Private Hot Tub - Walk to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Southernmost Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $2382 per night (USD)Expedia
From $709 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 $709 per night (USD)VRBO
From $198 per night (USD)Expedia
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 $198 per night (USD)Expedia
From $655 per night (USD)VRBO
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $655 per night (USD)VRBO
From $405 per night (USD)Expedia
Watch Sunsets from Your Deck, Shared Pool\/Hot Tub - Perfect for the Whole Family
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $405 per night (USD)Expedia
From $599 per night (USD)VRBO
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 $599 per night (USD)VRBO
From $432 per night (USD)Expedia
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 $432 per night (USD)Expedia
From $407 per night (USD)VRBO
Cozy Dog-Friendly Condo w\/ Shared Pool, Hot Tub, Private Deck & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Catalina Suite 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $407 per night (USD)VRBO
From $297 per night (USD)Expedia
Key Largo Paradise
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Key Largo vacation in our slice of paradise. Trailer sleeps 6. Enjoy the amenities of a giant 60" television, outdoor ba ...
From $297 per night (USD)Expedia
From $496 per night (USD)VRBO
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 $496 per night (USD)VRBO
From $1446 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 $1446 per night (USD)Expedia
From $961 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 $961 per night (USD)VRBO
From $1014 per night (USD)Expedia
Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mar Y Sol is a beautiful oceanfront condominium featuring three bedrooms and two and a half baths, located at 1800 Atlan ...
From $1014 per night (USD)Expedia
From $387 per night (USD)VRBO
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $387 per night (USD)VRBO
From $724 per night (USD)Expedia
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 $724 per night (USD)Expedia
Click For PricingVRBO
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 PricingVRBO
From $3918 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 $3918 per night (USD)Expedia
From $776 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 $776 per night (USD)VRBO
From $376 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 $376 per night (USD)Expedia
From $337 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 $337 per night (USD)VRBO
From $475 per night (USD)Expedia
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 $475 per night (USD)Expedia
From $152 per night (USD)VRBO
Key Largo Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The property is located in Pirates Cove (mile marker 99 bayside), which is an early Key Largo development that is quiet ...
From $152 per night (USD)VRBO
From $254 per night (USD)Expedia
Comfortable Waterfront Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $254 per night (USD)Expedia
From $587 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 $587 per night (USD)VRBO
From $640 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 $640 per night (USD)Expedia
From $758 per night (USD)VRBO
Marina Villa 3 Bedroom townhome on Oceanside
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This marina facing 3 bedroom townhome is spacious and beautifully decorated. Relax with the whole family at this peacef ...
From $758 per night (USD)VRBO
From $389 per night (USD)Expedia
Fins to the Left 2 bed 2 bath Duplex w\/ Cabana Club & dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy some changes in attitude and latitude in this waterfront beauty! This is a two bedroom, two bath, stilted, one-hal ...
From $389 per night (USD)Expedia
From $648 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 $648 per night (USD)VRBO
From $462 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 $462 per night (USD)Expedia
From $1377 per night (USD)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 ...
From $1377 per night (USD)VRBO
From $948 per night (USD)Expedia
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 5
- Bathrooms:
- 6
- 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 $948 per night (USD)Expedia
Click For PricingVRBO
7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $241 per night (USD)Expedia
Villa Paradise | 4 bed\/2 bath canalfront home on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Brand new 60-foot dock! Villa Paradise is the perfect home base for your Florida Keys adventure. Just four canals in fr ...
From $241 per night (USD)Expedia
From $1135 per night (USD)VRBO
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 $1135 per night (USD)VRBO
From $286 per night (USD)Expedia
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)Expedia
From $306 per night (USD)VRBO
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $306 per night (USD)VRBO
From $432 per night (USD)Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $432 per night (USD)Expedia
From $818 per night (USD)VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $818 per night (USD)VRBO
From $516 per night (USD)Expedia
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 $516 per night (USD)Expedia
From $344 per night (USD)VRBO
Waterfront home with gorgeous patio, WiFi, gas grill, & great location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Key Colony Beach Waterfront Villa Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $344 per night (USD)VRBO
From $456 per night (USD)Expedia
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 ...
From $456 per night (USD)Expedia
From $463 per night (USD)VRBO
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 $463 per night (USD)VRBO
From $359 per night (USD)Expedia
water at your back door
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $570 per night (USD)VRBO
Stylish Dog-Friendly Condo with Balcony - In Heart of the Historic District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Kingfish Keep On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $570 per night (USD)VRBO
From $503 per night (USD)Expedia
Condo on Duval with WiFi, Hot Tub, & Private Parking - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $503 per night (USD)Expedia
From $853 per night (USD)VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $853 per night (USD)VRBO
From $367 per night (USD)Expedia
Contemporary Seaside Cottage with a Private Hot Tub & Shared, Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Heron Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $367 per night (USD)Expedia
From $708 per night (USD)VRBO
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Saint Barts Suite 303 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $708 per night (USD)VRBO
From $501 per night (USD)Expedia
Waterfront house with covered patio, private pool, & 75' dock - dogs welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Magic in Marathon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $501 per night (USD)Expedia
From $397 per night (USD)VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $397 per night (USD)VRBO
From $306 per night (USD)Expedia
Queen’s Lair Rockhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $343 per night (USD)VRBO
Seas The Day 3bed\/2.5bath updated with great outdoor space
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Seas the Day is a stunning 3bed/2.5bath townhouse style single family home right in the heart of Marathon. The home fe ...
From $343 per night (USD)VRBO
From $406 per night (USD)Expedia
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $406 per night (USD)Expedia
From $380 per night (USD)VRBO
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 $380 per night (USD)VRBO
From $708 per night (USD)Expedia
Amazing condo with pool & hot tub - ideal for exploring Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrise Suites - Cat Island Suite 205 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $708 per night (USD)Expedia
From $130 per night (USD)VRBO
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $130 per night (USD)VRBO
From $1970 per night (USD)Expedia
Dog-Friendly, Oceanfront Duplex with Private Beach Access & Dock
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Beachfront Ocean Duplex Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $1970 per night (USD)Expedia
From $5037 per night (USD)VRBO
Spacious dog-friendly retreat with 3 hot tubs - near Duval Street & the beach
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Southernmost Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $5037 per night (USD)VRBO
From $557 per night (USD)Expedia
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Bonaire Suite 210 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $557 per night (USD)Expedia
From $328 per night (USD)VRBO
Bright & Breezy Top Floor Ocean View Condo w\/ Double Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this ...
From $328 per night (USD)VRBO
From $936 per night (USD)Expedia
Comfortable Condo with Pool, Private Balcony, & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Ocean View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $936 per night (USD)Expedia
From $185 per night (USD)VRBO
Quiet & Stress Free canal home with private dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The home has 3 bedrooms and 2 bath. The dock has space for a boat up to 30’. Come and enjoy the beautiful surroundings ...
From $185 per night (USD)VRBO
From $429 per night (USD)Expedia
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $429 per night (USD)Expedia
From $222 per night (USD)VRBO
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $222 per night (USD)VRBO
From $431 per night (USD)Expedia
Dog-friendly resort condo with pool & hot tub, private parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Saint Croix Suite 212 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $431 per night (USD)Expedia
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Fresh Getaway w\/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Hueso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
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From $527 per night (USD)Expedia
Condo on Duval Street - Walk to Beach & Southernmost Point, Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Yellowfin Ledge On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $527 per night (USD)Expedia
From $500 per night (USD)VRBO
Dog-friendly condo in prime location - walk to dining & sights, near the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $500 per night (USD)VRBO
From $1141 per night (USD)Expedia
Southernmost View | Pool & H20 Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fro ...
From $1141 per night (USD)Expedia
From $1280 per night (USD)VRBO
Lovely dog-friendly home with guest cottage & private pool - great location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1280 per night (USD)VRBO
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Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
- Bedrooms:
- 2
- 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 ...
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From $218 per night (USD)VRBO
200ft of Waterfront with Tiki & Heated Pool - Boaters Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Raised waterfront home at the start of the Florida Keys (Mile Marker 112) with all around views of waterway and Barnes S ...
From $218 per night (USD)VRBO
From $571 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 $571 per night (USD)Expedia
From $743 per night (USD)VRBO
Peaceful condo in Duval Square\/Old Town with lush gardens, pool, & chic decor
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Bonita at Duval Square R1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $743 per night (USD)VRBO
From $376 per night (USD)Expedia
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Leeward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $376 per night (USD)Expedia
From $143 per night (USD)VRBO
HUGE DISCOUNT FOR DECEMBER Half off!!. Book now!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise ...
From $143 per night (USD)VRBO
From $345 per night (USD)VRBO
Beautiful vacation home in the heart of Islamorada , Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the hom ...
From $345 per night (USD)VRBO
From $628 per night (USD)VRBO
Bright condo with charms of historic Key West - amazing walkable locale
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $628 per night (USD)VRBO
From $630 per night (USD)Expedia
Renovated Waterfront Modern Luxury, Lagoon, Marina, Tennis, Bikes, Pickleball
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
If your dates are not available or if you are looking for two units, check out my other VRBO Unit #802759. Enter the nu ...
From $630 per night (USD)Expedia
From $549 per night (USD)VRBO
★Remodeled tropical delight townhome★private plunge pool close to fun activities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet -1,000m ...
From $549 per night (USD)VRBO
From $557 per night (USD)Expedia
**CONCH GET ENOUGH at The Truman Annex in Key West**
- Bedrooms:
- 3
- 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 $557 per night (USD)Expedia
From $467 per night (USD)VRBO
CLOSE TO PERFECT at Key West Golf Club - 2\/2.5 w\/ Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
CLOSE TO PERFECT, far from normal! This stunning 2 bedroom, 2.5 bathroom townhouse with private pool will check all the ...
From $467 per night (USD)VRBO
From $1295 per night (USD)Expedia
Boaters’ Paradise - Marlin Bay Resort & Marina
- Bedrooms:
- 5
- Bathrooms:
- 5
- 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 $1295 per night (USD)Expedia