Monroe Area Rentals
- From $412 per night (USD)
VRBO
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)VRBO
- From $1040 per night (USD)
Expedia
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)Expedia
- From $427 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 $427 per night (USD)VRBO
- From $247 per night (USD)
Expedia
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)Expedia
- From $237 per night (USD)
VRBO
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $237 per night (USD)VRBO
- From $643 per night (USD)
Expedia
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)Expedia
- From $493 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 $493 per night (USD)VRBO
- From $70 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 $70 per night (USD)Expedia
- From $226 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 $226 per night (USD)VRBO
- From $264 per night (USD)
Expedia
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)Expedia
- From $385 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 $385 per night (USD)VRBO
- From $349 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 $349 per night (USD)Expedia
- From $712 per night (USD)
VRBO
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)VRBO
- From $315 per night (USD)
Expedia
**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)Expedia
- Click For Pricing
VRBO
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 $1263 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 $1263 per night (USD)Expedia
- From $654 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 $654 per night (USD)VRBO
- From $434 per night (USD)
Expedia
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)Expedia
- From $475 per night (USD)
VRBO
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)VRBO
- From $256 per night (USD)
Expedia
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)Expedia
- From $192 per night (USD)
VRBO
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)VRBO
- From $315 per night (USD)
Expedia
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)Expedia
- From $599 per night (USD)
VRBO
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)VRBO
- From $890 per night (USD)
Expedia
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)Expedia
- From $410 per night (USD)
VRBO
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)VRBO
- From $338 per night (USD)
Expedia
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)Expedia
- From $587 per night (USD)
VRBO
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)VRBO
- From $324 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 $324 per night (USD)Expedia
- From $130 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 $130 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $221 per night (USD)
VRBO
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)VRBO
- From $879 per night (USD)
Expedia
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)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 $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)
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 $887 per night (USD)VRBO
- From $250 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 $250 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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)VRBO
- From $275 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 $275 per night (USD)Expedia
- From $220 per night (USD)
VRBO
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)VRBO
- From $330 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 $330 per night (USD)Expedia
- From $55 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 $55 per night (USD)VRBO
- From $340 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 $340 per night (USD)Expedia
- From $258 per night (USD)
VRBO
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)VRBO
- From $402 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 $402 per night (USD)Expedia
- From $108 per night (USD)
VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $108 per night (USD)VRBO
- From $157 per night (USD)
Expedia
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Village - Tropical Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $157 per night (USD)Expedia
- From $166 per night (USD)
VRBO
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 $166 per night (USD)VRBO
- From $371 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 $371 per night (USD)Expedia
- From $435 per night (USD)
VRBO
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 $435 per night (USD)VRBO
- From $266 per night (USD)
Expedia
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 $266 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Queen’s Lair Rockhouse
- Bedrooms:
- 3
- 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 $225 per night (USD)VRBO
- From $259 per night (USD)
Expedia
Seas The Day 3bed\/2.5bath updated with great outdoor space
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $259 per night (USD)Expedia
- From $288 per night (USD)
VRBO
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $288 per night (USD)VRBO
- From $261 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 $261 per night (USD)Expedia
- From $400 per night (USD)
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 ...
From $400 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $59 per night (USD)
VRBO
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 $59 per night (USD)VRBO
- From $182 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 $182 per night (USD)Expedia
- From $375 per night (USD)
VRBO
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 $375 per night (USD)VRBO
- From $146 per night (USD)
Expedia
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 $146 per night (USD)Expedia
- From $932 per night (USD)
VRBO
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 $932 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Dog-Friendly Retreat in Casa Marina with Shared Pool, WiFi, and Walkable Locale
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Tropical Village - Toon Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $324 per night (USD)Expedia
- From $2550 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 $2550 per night (USD)VRBO
- From $250 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 $250 per night (USD)Expedia
- From $269 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 $269 per night (USD)VRBO
- From $75 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 $75 per night (USD)Expedia
- From $158 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 $158 per night (USD)VRBO
- From $285 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 $285 per night (USD)Expedia
- From $161 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 $161 per night (USD)VRBO
- From $311 per night (USD)
Expedia
Dog-friendly resort condo with pool & hot tub, private parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Saint Croix Suite 212 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $311 per night (USD)Expedia
- From $791 per night (USD)
VRBO
Southernmost View by Brightwild | 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 $791 per night (USD)VRBO
- From $749 per night (USD)
Expedia
Lovely 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 $749 per night (USD)Expedia
- Click For Pricing
VRBO
Serene dog-friendly haven with pool access, central AC, & walkable locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Village - Southern Cross Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
Click For PricingVRBO
- From $191 per night (USD)
Expedia
Dog-friendly condo in prime location - walk to dining & sights, near the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $191 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:
- 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 ...
Click For PricingVRBO
- From $289 per night (USD)
Expedia
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 $289 per night (USD)Expedia
- From $315 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 homeown ...
From $315 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $329 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 $329 per night (USD)VRBO
- From $91 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 $91 per night (USD)Expedia
- From $127 per night (USD)
VRBO
SPECIAL SUMMER SALE RATES ONLY JULY LEFT!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SEE SPECIAL POSTED RATES MAY-JULY! Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ...
From $127 per night (USD)VRBO
- From $469 per night (USD)
Expedia
Bright condo with private hot tub - amazing walkable locale
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $469 per night (USD)Expedia
- From $693 per night (USD)
VRBO
Renovated Waterfront Modern Luxury, Lagoon, Marina, Tennis, Bikes, Pickleball
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $693 per night (USD)VRBO
- From $429 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 $429 per night (USD)Expedia
- Click For Pricing
Expedia
Paradise Cove TOO!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Paradise! This beautiful open water open features panoramic views. 4 bedrooms and 3.5 baths provides tons of ...
Click For PricingExpedia
- From $322 per night (USD)
Expedia
★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 $322 per night (USD)Expedia
- From $189 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 $189 per night (USD)VRBO
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Expedia
Boaters’ Paradise - Marlin Bay Resort & Marina
- Bedrooms:
- 5
- 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 ...
Click For PricingExpedia
- From $250 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 $250 per night (USD)VRBO
- From $185 per night (USD)
Expedia
Modern 2BR Condo Old Town\/Balcony & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action ...
From $185 per night (USD)Expedia
- From $377 per night (USD)
VRBO
Green Goddess - 4 BD\/3 BA Amazing 360 Degree 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 $377 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Lil' Bit | Adorable Cottage on Quiet Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This classic "conch" home is modern ...
From $139 per night (USD)Expedia
- From $321 per night (USD)
VRBO
W01 - Beautiful family home with pool and dockage and tiki hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly updated 3 bedroom, 2 bathroom canal-front home. Great boating location with easy access to the Atlantic and 100' o ...
From $321 per night (USD)VRBO
- From $2000 per night (USD)
Expedia
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2000 per night (USD)Expedia
- From $357 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 $357 per night (USD)VRBO
- From $560 per night (USD)
Expedia
Sky Suite on Duval by Brightwild | Condo w\/Balcony
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $560 per night (USD)Expedia
- From $204 per night (USD)
VRBO
Waterfront retreat with balcony views, kayak, SUP, central AC & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Palm Breeze - Villa 5030 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $204 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Kawama Yacht Club-Oceanfront Resort-Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Kawama Yacht Club, a Tropical Oceanside Resort in the heart of the Florida Keys (Oceanside Key Largo at Mile ...
From $400 per night (USD)Expedia
- From $1158 per night (USD)
VRBO
**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 $1158 per night (USD)VRBO
- From $766 per night (USD)
VRBO
For the most discriminating traveler...Oceanview! 525 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This sumptuous four bedroom oceanfront villa exudes luxury in every detail...the finest leather furnishings...custom woo ...
From $766 per night (USD)VRBO