Monroe Area, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Monroe Area, Florida on RentalSaver.com!

Monroe Area Rentals

Click For Pricing
VRBO
Gorgeous, Breath-taking Sunsets!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Located on the only cut in Key Largo that connects the bay to the ocean. Great fishing and scuba diving Dive shops and w ...
Click For Pricing
VRBO
From $874 per night (USD)
Expedia
Snorkel Shack on Sombrero 4 bedrooms 3 baths with pool and 100 Ft of Dockage
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Vaca-21-495 This home is located landside of Sombrero Light. If you take your boat or rent a boat it is a Lighthouse l ...
From $874 per night (USD)
Expedia
From $462 per night (USD)
VRBO
ANOTHER DAY IN PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $462 per night (USD)
VRBO
From $633 per night (USD)
Expedia
513 Mariners Club Key Largo | 3 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Infinite horizons...from this ground floor, luxury, three-bedroom, two and one-half-bath villa! A peaceful, relaxing ge ...
From $633 per night (USD)
Expedia
From $951 per night (USD)
VRBO
A SUNSET BREEZE Beautiful private home with pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $951 per night (USD)
VRBO
From $425 per night (USD)
Expedia
A SUNSET POOLSIDE in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $425 per night (USD)
Expedia
From $449 per night (USD)
VRBO
ARCHIPELAGO ll at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $449 per night (USD)
VRBO
From $282 per night (USD)
Expedia
ALHAMBRA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $282 per night (USD)
Expedia
From $452 per night (USD)
VRBO
SAILOR'S STORY at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $452 per night (USD)
VRBO
From $694 per night (USD)
Expedia
Key Colony Beach Republic – Island Living (KCB#19)
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Tropical 4BR pool home in Key Colony Beach with private upstairs and downstairs living areas. Upstairs: King master, Que ...
From $694 per night (USD)
Expedia
From $385 per night (USD)
VRBO
AQUA OASIS at The Truman Annex in Key West..
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $385 per night (USD)
VRBO
From $377 per night (USD)
Expedia
CONCH ISLAND at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $377 per night (USD)
Expedia
$*Casa-Amelia-Key-West* 1\/2 block off Duval Street$
From $587 per night (USD)
VRBO
*Casa-Amelia-Key-West* 1\/2 block off Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $587 per night (USD)
VRBO
From $719 per night (USD)
Expedia
412 Mariners Club Key Largo | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
No need to search further for your perfect vacation home-away-from-home! This sought-after, 3-story corner townhouse is ...
From $719 per night (USD)
Expedia
$Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony$
From $576 per night (USD)
VRBO
Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $576 per night (USD)
VRBO
From $210 per night (USD)
Expedia
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $210 per night (USD)
Expedia
From $569 per night (USD)
VRBO
🌸Home (#4) ”A WAVE💦 FROM IT ALL” (Partial Ocean View -approximately 150 ft from beach entrance)🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
#4: A WAVE💦 FROM IT ALL (Partial Ocean View Property-approximately 150 ft from beach entrance)🌸 Totally Private😉- Tur ...
From $569 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Boater's Paradise
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—per ...
From $404 per night (USD)
Expedia
From $1077 per night (USD)
VRBO
Commodore's Cove - Epic Location 1 Block to Duval
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $1077 per night (USD)
VRBO
From $2255 per night (USD)
Expedia
Commodore's Compound - Epic Location Near Duval
Bedrooms:
7
Bathrooms:
10
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2255 per night (USD)
Expedia
From $1435 per night (USD)
VRBO
Steps from Duval, Private Hot Tub - Seaport Suite
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Located in the heart of Old Town Key West, Seaport Suite is the ideal getaway for large groups of up to 12 gues ...
From $1435 per night (USD)
VRBO
From $460 per night (USD)
Expedia
SEASCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $460 per night (USD)
Expedia
From $296 per night (USD)
VRBO
TROPICAL VINEYARD at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $296 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ocean views from living room and master bedroom!! Get your inspiration every morning, directly on the sea from one of t ...
From $376 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean views from living room and master bedroom!! Get your inspiration every morning, directly on the sea from one of t ...
From $439 per night (USD)
VRBO
$Luxurious Top Floor 2 Bedroom Suite w\/ Unobstructed Ocean Views$
From $303 per night (USD)
Expedia
Luxurious Top Floor 2 Bedroom Suite w\/ Unobstructed Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this ...
From $303 per night (USD)
Expedia
From $1011 per night (USD)
VRBO
311 Mariners Club Key Largo | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If this villa has come up in your search for that ‘special’ vacation accommodation…you can stop right now. Villa 311 Mar ...
From $1011 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Incredible Views from Ocean Lovers Suite [Ocean Pointe 5413]
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME Classic coastal décor greets you in this one bedroom, one bathroom ...
From $276 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Private Heated Pool, Cabana, & Prime Key West Location Near Truman Annex!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated po ...
From $503 per night (USD)
VRBO
$UNIQUE AND BEAUTIFUL \BONNE-VIE at SEA\<br>$
From $98 per night (USD)
Expedia
UNIQUE AND BEAUTIFUL \"BONNE-VIE at SEA\"<br>
Bedrooms:
1
Bathrooms:
3
Sleeps:
2
Hi there and welcome to our Bonnie -vie! She's anchored about 3/4 mi from the base marina in a beautiful cove. The BOAT ...
From $98 per night (USD)
Expedia
From $303 per night (USD)
VRBO
SPECTACULAR OCEAN VIEWS FROM THIS MODERN BEACH CONDO
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our property is located on 38 acres surrounded by nature and the ocean. The property is gated with 24 hour security. En ...
From $303 per night (USD)
VRBO
From $383 per night (USD)
Expedia
One Of A Kind Ocean Front With Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This one of a kind ocean front property offers much more than just the view. With 3 bedrooms and 2 bathrooms this 1800 s ...
From $383 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Relax & Recharge at our Quiescent 2 BR Condo with Stunning Ocean Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Delight in a quiet escape, with open ocean views, from our two bedroom condo located in the 3rd building at Ocean Pointe ...
From $319 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $493 per night (USD)
Expedia
From $254 per night (USD)
VRBO
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Huge terrace- accessible from every room! Spacious and clean. Peaceful and away from the highway, yet near everything! S ...
From $254 per night (USD)
VRBO
From $928 per night (USD)
Expedia
Fishermen`s Paradise | Waterfront home with huge pool, 220-foot dock & gorgeous interior
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to your perfect island retreat! This freshly remodeled three-bedroom, four-bathroom vacation home on Big Pine of ...
From $928 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great views of Sugarloaf Sound from this ground-level midcentury-era home that offers expansive sound frontage perfect f ...
From $282 per night (USD)
VRBO
From $1457 per night (USD)
Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1457 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Amazing Pool & Canal Ground Level Home, Ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is an amazing Ground level Pool and Canal home. With stunning concrete ground pool and Jacuzzi tub. (POOL HEAT AV ...
From $353 per night (USD)
VRBO
From $392 per night (USD)
Expedia
ADRIFT in Key West at the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completel ...
From $392 per night (USD)
Expedia
$Cayman Cottage | 3 bed\/2 bath boating home on Ramrod Key$
From $229 per night (USD)
VRBO
Cayman Cottage | 3 bed\/2 bath boating home on Ramrod Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Cayman Cottage, a charming three-bedroom, two-bathroom monthly vacation rental in Breezeswept Beach Estates on ...
From $229 per night (USD)
VRBO
$Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key$
From $230 per night (USD)
Expedia
Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stai ...
From $230 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $222 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Cedar Cottage | Adorable canalfront cottage, lots of dockage on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to your perfect slice of paradise in the heart of the Florida Keys! This newly remodeled 2 bed/2 bath home on a ...
From $222 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilt ...
From $342 per night (USD)
VRBO
$OPEN WATER PARADISE 2\/2 HALF DUPLEX IN KEY COLONY BEACH MARATHON, FL 34$
From $307 per night (USD)
Expedia
OPEN WATER PARADISE 2\/2 HALF DUPLEX IN KEY COLONY BEACH MARATHON, FL 34
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Remodeled! Half Duplex with walk thru layout! Under new ownership as of November 2020. MODERN / CLEAN / SPACIOUS *** ...
From $307 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $217 per night (USD)
VRBO
$3 BR\/ 2 BA, Canal Front Home, Private Dock for 40' Boat & 1 mi to Beach$
From $342 per night (USD)
Expedia
3 BR\/ 2 BA, Canal Front Home, Private Dock for 40' Boat & 1 mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Kickin' Back Reel Time, Your Home Away from Home in Marathon, FL. This beautifully updated, canal front home ...
From $342 per night (USD)
Expedia
From $538 per night (USD)
VRBO
FOREVER YOUNG at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $538 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Escape to Coastal Ways - Spacious Oceanfront Suite at Ocean Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our well-appointed condo provides the perfect home away from home. Step onto your private balcony and soak in the mesmer ...
From $278 per night (USD)
Expedia
From $401 per night (USD)
VRBO
ABOUT TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $401 per night (USD)
VRBO
From $385 per night (USD)
Expedia
HAVANA VIEWS at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $385 per night (USD)
Expedia
From $326 per night (USD)
VRBO
SAND CRAB CABANA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $326 per night (USD)
VRBO
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $473 per night (USD)
Expedia
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $473 per night (USD)
Expedia
$Casa Chiquita - 3\/2 Pool - Waterfront - 75’ Dock - Ground Level$
From $488 per night (USD)
VRBO
Casa Chiquita - 3\/2 Pool - Waterfront - 75’ Dock - Ground Level
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Kick back, unplug, and chum up some yellowtail at one of the best locations in the middle keys! Casa Chiquita is a rece ...
From $488 per night (USD)
VRBO
From $271 per night (USD)
Expedia
The Estela, Old Town Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away just 1 block from the action of Duval Street lies our newest space located at 613 Fleming Street. Find your ...
From $271 per night (USD)
Expedia
Click For Pricing
VRBO
Ocean views, great for fishing and kayaking, the best family experience
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For Pricing
VRBO
From $420 per night (USD)
Expedia
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Flori ...
From $420 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Ocean Oasis at Ocean Pointe Key Largo Pool Jacuzzi Beach in a Safe Gated Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Photos you are looking at are of our awesome unit. Choose careful because some rentals will assign your unit upon arriva ...
From $244 per night (USD)
VRBO
From $111 per night (USD)
Expedia
Live Like A Local @ Largo Lookout, Lovely Waterview, MM 99.5, Pets Welcome, 28 Nt Min
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Waterfront 1 Bedroom, 1 Bath Apartment, Located in Heart of Key Largo, Sleeps 4, Pet Friendly Largo Lookout has a minimu ...
From $111 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Oceanfront Luxury Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seagulls Condominiums Islamorada Tavernier Key Largo New Lazy Boy recliner added to our open concept living room. Uppe ...
From $132 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Islamorada Waterfront Paradise with 5 Bedrooms, Pool and Dock
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Escape to your tropical island paradise in the heart of the Florida Keys! Nestled in cross keys location, to Tavernier C ...
From $602 per night (USD)
Expedia
From $1662 per night (USD)
VRBO
Villa Murano - A Private Retreat in the Florida Keys
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Villa Murano for 14 plus guests, for families, for gatherings, for corporate retreats for celebrations, for a phenomenal ...
From $1662 per night (USD)
VRBO
From $403 per night (USD)
Expedia
A quiet relaxing place that you can disconnect from real life. Comforts of home
Bedrooms:
4
Bathrooms:
3
Sleeps:
12
Clean, Comfortable, Private, Remodeled, full of amenities, new furniture, relaxing and peaceful. 7+ restaurants at walki ...
From $403 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Direct Ocean View from Your Condo-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $368 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Oceanside 3/3 located on beautiful 10 acre harbor. Amazing natural surroundings, harbor & ocean views. New furnishings, ...
From $449 per night (USD)
Expedia
From $1273 per night (USD)
VRBO
Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Waterfront Wonder Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1273 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $356 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and c ...
From $241 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Charming & Tranquil Condo [Ocean Pointe 2208]
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your vacation starts the moment you step foot into this simply brilliant coastal condo that sits next to the Atlantic Oc ...
From $307 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $326 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Steps To The Beach And The Sunrise-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnis ...
From $326 per night (USD)
Expedia
From $267 per night (USD)
VRBO
1 rm peaceful ocean view retreat in the Florida Keys!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key ...
From $267 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Stone Throw Famous Duval Street Location-No Contact Check-In
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $246 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $803 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in ...
From $283 per night (USD)
Expedia
Click For Pricing
VRBO
Sunset of the bay in Key Largo, Florida
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
One bedroom apartment and 5th floor overlooking bay. Huge balcony, full kitchen, one bedroom, one bath. Community boat d ...
Click For Pricing
VRBO
From $282 per night (USD)
Expedia
A PLEASANT STAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $282 per night (USD)
Expedia
Click For Pricing
VRBO
ANGEL FISH at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...
Click For Pricing
VRBO
From $497 per night (USD)
Expedia
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $497 per night (USD)
Expedia
From $668 per night (USD)
VRBO
TROPICAL EXECUTIVE at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $668 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Keys Villa - Secluded tropical paradise located on the water!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
From $388 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Waterfront Cottage at Tavernier, Florida Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our beautiful Waterfront Cottage offers breathtaking views of the ocean, a private deck with a propane grill, and a won ...
From $246 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Gorgeous house, GUARANTEED to beat any price for a 3BR in Marathon
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Three bedrooms and 2 bathrooms in open concept with everything you need in the heart of the Keys. Ample parking spaces ...
From $374 per night (USD)
Expedia
$Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking$
From $640 per night (USD)
VRBO
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $640 per night (USD)
VRBO
$Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking$
From $705 per night (USD)
Expedia
Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $705 per night (USD)
Expedia
From $949 per night (USD)
VRBO
Marlin House @ Tarpon Point
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Stunning ocean views from all living levels & a waterfront pool! The Space: Welcome to the captivating Marlin ...
From $949 per night (USD)
VRBO
From $650 per night (USD)
Expedia
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...
From $650 per night (USD)
Expedia
Click For Pricing
VRBO
2 BR at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium ...
Click For Pricing
VRBO
$Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $815 per night (USD)
Expedia
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $815 per night (USD)
Expedia
$Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $585 per night (USD)
VRBO
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $585 per night (USD)
VRBO
From $724 per night (USD)
Expedia
Elegant waterfront home with private pools, hot tub, & dock - walk to beach
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Key Quest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $724 per night (USD)
Expedia
$New listing 3bd\/2bt Sleeps 8 \Sunset Paradise Villa\ on canal Big Pine Key$
From $247 per night (USD)
VRBO
New listing 3bd\/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a 3 Bedroom/2 Bath cana ...
From $247 per night (USD)
VRBO
From $583 per night (USD)
Expedia
LUXURY VIP SUITE - INDOOR PICKLEBALL - STUNNING OCEAN VIEWS - OCEANFRONT RESORT!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $583 per night (USD)
Expedia
$LICENSED MANAGER - MODERN 2\/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!$
From $308 per night (USD)
VRBO
LICENSED MANAGER - MODERN 2\/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townho ...
From $308 per night (USD)
VRBO
From $524 per night (USD)
Expedia
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $524 per night (USD)
Expedia
$LICENSED MGER - MODERN 2\/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!$
From $408 per night (USD)
VRBO
LICENSED MGER - MODERN 2\/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
You have just discovered one of the most unique properties in the heart of Key Largo. This oceanfront condo is located i ...
From $408 per night (USD)
VRBO
From $678 per night (USD)
Expedia
808 Mariners Club | 4 Bed, 3.5 Bath
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Designer upgrades make this luxury, two-story townhouse with over 2600 sq of living space the perfect home-away-from-hom ...
From $678 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Relax in the Keys
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Completely remodeled 1st floor - 90’ TV, recliner, full size bathroom, kitchen 2nd floor, 2 bedrooms, 2 bathrooms, kit ...
From $292 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Palm Villa SPECIAL MAY 249 per night includes dock & Cabana Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This Villa has a CALIFORNIA KING BED in the Master Bedroom & a Queen Bed in the guest room plus Queen Sleeper Sofa in Li ...
From $407 per night (USD)
Expedia

Search Your Destination Now!

Monroe Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals