
Monroe Area Rentals

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VRBO
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For PricingVRBO
- From $432 per night (USD)
Expedia
Waterfront Half-Duplex with 30-Ft. Dock, Sitting Pool, and Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Fantastic Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $432 per night (USD)Expedia
- From $152 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 $152 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Guests must register at the office unless it is after hours in which you will register at the Guard House. Unit 175 is c ...
From $223 per night (USD)Expedia
- From $554 per night (USD)
VRBO
Little Paradise, Historic Harbor Old Town Key West 2/1.5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $554 per night (USD)VRBO
- From $585 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 $585 per night (USD)Expedia
- From $456 per night (USD)
VRBO
Marina Villa 212 3/3 Pools, Marina and Ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Best vacation rental to explore the Florida keys. Marina Villa 212 (3b/3b) with Marina and ocean views. Escape to pa ...
From $456 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Fins to the Left in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy some changes in attitude and latitude in this waterfront beauty! This is a two bedroom, two bath, stilted, one-hal ...
From $385 per night (USD)Expedia
- From $508 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 $508 per night (USD)VRBO
- From $464 per night (USD)
Expedia
Vacation Home on Open Gulf with Fantastic Panoramic View
- Bedrooms:
- 3
- 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 $464 per night (USD)Expedia
- From $1377 per night (USD)
VRBO
Gated Vacation Oasis Luxury Home Sunset Point Key Largo
- Bedrooms:
- 4
- 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 $838 per night (USD)
Expedia
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $838 per night (USD)Expedia
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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 $246 per night (USD)
VRBO
Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to Villa Paradise – Your Monthly Retreat in the Florida Keys! Discover the ultimate Florida Keys getaway at Vill ...
From $246 per night (USD)VRBO
- From $286 per night (USD)
VRBO
House full of life with pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
House in Key Largo. Great Home for a big family, 5 bedrooms and 4 full baths. Jacuzzi. Pool (8x14') with a deck. Can bri ...
From $286 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $292 per night (USD)Expedia
- From $429 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 $429 per night (USD)VRBO
- From $571 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 $571 per night (USD)Expedia
- From $421 per night (USD)
VRBO
Great Family Vacation Rental.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $421 per night (USD)VRBO
- From $218 per night (USD)
Expedia
Waterfront home with gorgeous patio, WiFi, gas grill, & great location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Key Colony Beach Waterfront Villa Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $218 per night (USD)Expedia
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VRBO
Beautiful Home with Great Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful home in the Florida Keys, close to everything. Amazing water views and sunrises. All Key Largo activities to e ...
Click For PricingVRBO
- From $359 per night (USD)
Expedia
water at your back door
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $359 per night (USD)Expedia
- From $525 per night (USD)
VRBO
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $525 per night (USD)VRBO
- From $660 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 $660 per night (USD)Expedia
- From $324 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 $324 per night (USD)VRBO
- From $254 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 $254 per night (USD)Expedia
- From $306 per night (USD)
VRBO
Queen’s Lair Rockhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $306 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Seas the Day in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Seas the Day Modern Townhome with Swim Spa in MarathonWelcome to Seas the Day, a beautifully designed 3-bedroom, 2.5-ba ...
From $332 per night (USD)Expedia
- From $282 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 $282 per night (USD)VRBO
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Expedia
Fresh Getaway w/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
- Bedrooms:
- 3
- 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 $340 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 $340 per night (USD)VRBO
- From $130 per night (USD)
Expedia
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
- Bedrooms:
- 1
- 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)Expedia
- From $1155 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 $1155 per night (USD)VRBO
- From $275 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 $275 per night (USD)Expedia
- From $272 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 $272 per night (USD)VRBO
- From $559 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 $559 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 $352 per night (USD)
Expedia
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $352 per night (USD)Expedia
- From $143 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 $143 per night (USD)VRBO
- From $339 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 $339 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Pool & Parking & Pet Friendly - Southernmost View
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fro ...
From $354 per night (USD)VRBO
- From $930 per night (USD)
Expedia
Charming dog-friendly home with guest cottage & private pool - great location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $930 per night (USD)Expedia
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VRBO
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For PricingVRBO
- From $241 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 $241 per night (USD)Expedia
- From $366 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 $366 per night (USD)VRBO
- From $670 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 $670 per night (USD)Expedia
- From $349 per night (USD)
VRBO
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 $349 per night (USD)VRBO
- From $230 per night (USD)
Expedia
BOOK YOUR DREAM VACATION at BEACON REEF - Specials!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Special for September/October/December. World Famous Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / * ...
From $230 per night (USD)Expedia
- From $464 per night (USD)
VRBO
Bright condo with charms of historic Key West - amazing walkable locale
- Bedrooms:
- 2
- 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 $464 per night (USD)VRBO
- From $277 per night (USD)
Expedia
Imagine in the Keys - Venture Out Unit 073
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine in the Keys VO073 35' Dockage Canal front 2Bd/2Ba This home features 2Bd/2Ba and is located only 3 lots from op ...
From $277 per night (USD)Expedia
- From $514 per night (USD)
VRBO
Keys Relaxing Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Have fun with the whole family at this stylish place. Explore the Florida Keys from this central location. Key Largo i ...
From $514 per night (USD)VRBO
- From $401 per night (USD)
Expedia
★Remodeled tropical delight townhome★private plunge pool close to fun activities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet -1,000m ...
From $401 per night (USD)Expedia
- From $502 per night (USD)
VRBO
**CONCH GET ENOUGH at The Truman Annex in Key West**
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $502 per night (USD)VRBO
- From $221 per night (USD)
Expedia
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool
- Bedrooms:
- 2
- 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 $221 per night (USD)Expedia
- From $2397 per night (USD)
VRBO
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 4
- 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 $2397 per night (USD)VRBO
- From $1116 per night (USD)
Expedia
Boaters’ Paradise - Marlin Bay Resort & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $1116 per night (USD)Expedia
- From $287 per night (USD)
VRBO
Executive Bay Club Bayfront/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $287 per night (USD)VRBO
- From $194 per night (USD)
Expedia
Modern 2BR Condo Old Town/Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $194 per night (USD)Expedia
- From $474 per night (USD)
VRBO
Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $474 per night (USD)VRBO
- From $396 per night (USD)
Expedia
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 $396 per night (USD)Expedia
- From $918 per night (USD)
VRBO
Balcony & Near Downtown - Sky Suite on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $918 per night (USD)VRBO
- From $243 per night (USD)
Expedia
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Palm Breeze - Villa 5030 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $243 per night (USD)Expedia
- From $476 per night (USD)
VRBO
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 $476 per night (USD)VRBO
- From $1600 per night (USD)
Expedia
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $1600 per night (USD)Expedia
- From $776 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $776 per night (USD)VRBO
- From $808 per night (USD)
Expedia
525 Mariners Club Key Largo | 4 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This sumptuous four bedroom oceanfront villa exudes luxury in every detail...the finest leather furnishings...custom woo ...
From $808 per night (USD)Expedia
- Click For Pricing
VRBO
Bahama Breeze in Key Colony Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of Key Colony Beach, this stunning waterfront home offers everything you need for an unforgettable ...
Click For PricingVRBO
- From $312 per night (USD)
Expedia
Luxury Condominium In Key Largo... Sunsets, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
From your balcony in the Kawama Tower, you get stunning vistas of ocean and palm trees. Enjoy the view from this complet ...
From $312 per night (USD)Expedia
- From $798 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $798 per night (USD)VRBO
- From $885 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $885 per night (USD)Expedia
- From $241 per night (USD)
VRBO
This Oceanfront Resort HAS IT ALL!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic 2 bedroom, 2 bath condo resort. Enjoy the breathtaking view of the Atlantic Ocean from the patio just steps fr ...
From $241 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Enjoy Caribbean weather in the USA. Summer openings!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is a bungalow with cathedral ceilings. It is spacious and sparkling clean. Our home is #655 at Venture Out on ...
From $223 per night (USD)Expedia
- From $798 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $798 per night (USD)VRBO
- From $353 per night (USD)
Expedia
Mermaid Magic in Key Colony Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful ground level spacious 3 bedroom 3 bathroom duplex. Updated kitchen with gorgeous wood cabinets and stainless a ...
From $353 per night (USD)Expedia
- From $359 per night (USD)
VRBO
Splash Pool- Key Colony Villa - KCB#4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our stunning waterfront unit in Key Colony Beach with its tropical outdoor living & instant ocean access from ...
From $359 per night (USD)VRBO
- From $645 per night (USD)
Expedia
New 4/3 Private Single Family - 2 min to ocean, kayaks, paddleboards, bicycles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Treasure at Sombrero Beach is a 2020 built single-family home on a large lot within walking distance to the beautif ...
From $645 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Beachy getaway with pool, water views, furnished patio, & dock access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
R & R Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $264 per night (USD)VRBO
- From $534 per night (USD)
Expedia
Sunrise Escape - Ocean Front Villa - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the sunrise while sitting on one of two terraces while sipping your morning coffee in the exclusive part of Kawama ...
From $534 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Fairway Villa w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $339 per night (USD)VRBO
- From $270 per night (USD)
Expedia
We have a deck water front perfect spot for fishing or relaxing the view
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
The property has a breath taking view of a bay Where you can fish 🐠 and enjoy the Catch of day it has out side Kichen a ...
From $270 per night (USD)Expedia
- From $687 per night (USD)
VRBO
Latitude Adjustment FLKeys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Latitude Adjustment, Islamorada, Florida This home is our families' paradise in the Florida Keys and we want to share it ...
From $687 per night (USD)VRBO
- From $626 per night (USD)
Expedia
612 Mariners Club | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) w ...
From $626 per night (USD)Expedia
- From $296 per night (USD)
VRBO
Ocean Point Retreat ~ Immaculate Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Private Beach, Fishing Pier, Fish Cleaning Station, Jr. Olympic pool, Spa, Pickleball Court, BBQ grills, nature ...
From $296 per night (USD)VRBO
- From $296 per night (USD)
Expedia
Coo Coo's Nest ~ Key Largo canal front 2/3 with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Beautiful pool home with dockage in the heart of Key Largo! The Space: Step into the enchanting Coo Coo's Nest ...
From $296 per night (USD)Expedia
- From $339 per night (USD)
VRBO
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $339 per night (USD)VRBO
- From $173 per night (USD)
Expedia
New Tiny House RV, Kayak, Beach, Marina, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Camper RV at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed, 1 Pull out Sofa, Single bed in Lof ...
From $173 per night (USD)Expedia
- From $247 per night (USD)
VRBO
Light, Bright & Nautical Condo - 5 min to Local Attractions [Ocean Pointe 1211]
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our beautifully designed oceanfront condo in Key Largo, nestled beside a tropical mangrove forest. The condo offer ...
From $247 per night (USD)VRBO
- From $364 per night (USD)
VRBO
Amazing Beach! Near John Pennekamp National Marine Sanctuary, 2 Outdoor Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Oceanfront family-friendly property with direct beach access and pool This listing is for a room within a hotel. ✦ You ...
From $364 per night (USD)VRBO
- From $530 per night (USD)
VRBO
Ohana Cay 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our island oasis, Ohana Cay! We would love to welcome you to our recently updated four bedroom/four bathroom ...
From $530 per night (USD)VRBO
- From $293 per night (USD)
VRBO
Vacation home in Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
AWESOME View of the Bay- from Chickee Hut Dock to Full Roof Top Patio. 2 Story. Large Master Bedroom with Steam Shower. ...
From $293 per night (USD)VRBO
- From $486 per night (USD)
VRBO
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $486 per night (USD)VRBO
- From $797 per night (USD)
Expedia
P00 - 4 Bedroom Pool Home overlooking Sombrero Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful 4 bedroom, 4 bath family home is located in the very desirable area of Sombrero Beach and is directly acr ...
From $797 per night (USD)Expedia
- From $414 per night (USD)
VRBO
By The Sea ~ Islamorada Home with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Canal front 2/2 with ocean views and relaxing breezes! The Space: This canal front two bedroom two bathroom ho ...
From $414 per night (USD)VRBO
- From $306 per night (USD)
Expedia
Latitude Adjustment in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Latitude Adjustment is a ground-level, updated half duplex featuring 2 bedrooms and 2 bathrooms. The master bedroom offe ...
From $306 per night (USD)Expedia
- From $260 per night (USD)
VRBO
P49 - Charming 2 bedroom, single family home just a short walk to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming all ground level, 2 bedroom, 2 bath home is walking distance to Sombrero Beach. This truly makes you feel ...
From $260 per night (USD)VRBO
- From $452 per night (USD)
Expedia
P03 - Charming 4 bedroom home with pool and dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home is located in the quiet and very desirable Coco Plum neighborhood, a few minutes' walk to the beach. ...
From $452 per night (USD)Expedia
- From $242 per night (USD)
VRBO
P41 - Beach Front condo with 2 bedrooms, 2 bath, pool and tennis courts!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Condo overlooking the natural beach of Coco Plum. This 2 bedroom, 2 bath congo unit offers 1,280 sq feet of living space ...
From $242 per night (USD)VRBO
- From $405 per night (USD)
Expedia
P78 - Charming beach home just down the road from Sombrero Beach. 3 bedroom 2...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 minute walk ...
From $405 per night (USD)Expedia
- From $441 per night (USD)
VRBO
P27 - Private Beach Access! Pool home with everything you need for an...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful 3 bedroom, 2 bath home located in the very desirable Key Colony Beach, boasts a large open floor plan, pr ...
From $441 per night (USD)VRBO
- From $252 per night (USD)
Expedia
P29 - Charming 3 bedroom 2 bath duplex with deep water dockage and Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Key Colony at its most charming! This 3 bedroom, 2 bathroom, half duplex is located in the heart of Marathon in Key Colo ...
From $252 per night (USD)Expedia