Monroe Area Rentals
From $242 per night (USD)VRBO
Gallego deluxe rental key largo Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Welcome to Calusa Campground, located in Key Largo, at the south of Florida. We are located at mile 101 ...
From $242 per night (USD)VRBO
From $523 per night (USD)Expedia
Charming 4-bedroom house in fabulous Key Colony Beach with AC, WIFI, Boatlift,
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a peaceful stay at this 4-bedroom house in Key Colony Beach. Marvel at the 1 king bed, 2 queen beds, and 2 twin be ...
From $523 per night (USD)Expedia
From $2188 per night (USD)VRBO
Parking, Pool & Pet Friendly - Catchlight House
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Welcome to your ultimate Key West getaway! This stunning 6-bed, 6.5-bath home perfectly blends comfort, style, ...
From $2188 per night (USD)VRBO
From $321 per night (USD)VRBO
Unwind with Stunning Sunset Views & Water Sports at Our Relaxing Hotel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to a beachfront oasis in Key Largo, just 1 hour from Miami. Walk to restaurants, bars, and attractions. Go fishi ...
From $321 per night (USD)VRBO
From $561 per night (USD)VRBO
Waterfront Retreat Perfect for Scenic Afternoon | Outdoor Pool and Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to a beachfront oasis in Key Largo, just 1 hour from Miami. Walk to restaurants, bars, and attractions. Go fishi ...
From $561 per night (USD)VRBO
From $368 per night (USD)VRBO
Peaceful Getaway with Beautiful Bayside Sunset | Room w\/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to a beachfront oasis in Key Largo, just 1 hour from Miami. Walk to restaurants, bars, and attractions. Go fishi ...
From $368 per night (USD)VRBO
From $279 per night (USD)VRBO
Spacious 4-bedroom Key Largo Villa steps from the pool, pickleball, & marina.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to paradise at 9802 Windward Avenue, nestled in the serene and sought after Landings of Largo community in South ...
From $279 per night (USD)VRBO
From $2600 per night (USD)Expedia
Parking, Pool & Pet Friendly - Larkshine House
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 18
Summary: Welcome to Larkshine House in Lunara Bay, Key West—a perfect retreat for families and large groups! This 8-bedr ...
From $2600 per night (USD)Expedia
From $168 per night (USD)VRBO
Contemporary Hideaway in the Heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. E ...
From $168 per night (USD)VRBO
From $225 per night (USD)Expedia
Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $225 per night (USD)Expedia
From $278 per night (USD)VRBO
Wonderful, Waterfront Home in Tavernier, Florida Keys, Sunsets for Miles!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This Tavernier bay front property boasts 4 inviting bedrooms, including 2 king beds and 2 queen beds comfortably sleepin ...
From $278 per night (USD)VRBO
From $166 per night (USD)Expedia
Lovely 2-bedroom condo in Key Largo with private beach, WiFi and fitness room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Your Key Largo adventure begins at this welcoming 2-bedroom condo on the water over looking the boat basin. Inside, you' ...
From $166 per night (USD)Expedia
From $230 per night (USD)VRBO
Charming 2-bedroom house in welcoming Islamorada with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brilliant house in Islamorada is a wonderful choice for guests seeking a cozy retreat. With 2 bedrooms, 2 bathrooms ...
From $230 per night (USD)VRBO
From $494 per night (USD)Expedia
Stunning 2BD Oceanfront Escape, Breathtaking Views - pool, hot tub and more
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Côte du Bonheur, your oceanfront retreat located in Key West. This 3rd Floor-level unit in the prestigious 18 ...
From $494 per night (USD)Expedia
From $306 per night (USD)VRBO
Into the Blues- Oceanfront Beach House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the perfect coastal vacation at Into The Blues, a stunning oceanfront rental property with panoramic views of ...
From $306 per night (USD)VRBO
From $145 per night (USD)Expedia
Canal-Front Key Largo Retreat w\/ Community Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Community Dock & Boat Ramp | Balcony w/ Water View | Gas Grill (Starter Propane Provided) Tropical bliss awaits at this ...
From $145 per night (USD)Expedia
From $322 per night (USD)VRBO
Your Home Away From Home! Comfortable Unit, Free Parking, Pool and Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $322 per night (USD)VRBO
From $379 per night (USD)Expedia
Escape to beautiful Islamorada!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in ...
From $379 per night (USD)Expedia
From $374 per night (USD)VRBO
Endless Summer Key Largo House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This Key Largo 5 bedroom, 3 bathroom home has all the amenities, entertainment, and comforts of a home on the water. Bri ...
From $374 per night (USD)VRBO
From $489 per night (USD)VRBO
Charming 3-bedroom house in Marathon with Pool and Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming home offers easy access to the ocean and boasts a delightful 10 X 20 pool with depths ranging from 3 to 5 ...
From $489 per night (USD)VRBO
From $711 per night (USD)VRBO
Atlantis House- beautiful residence close to beaches
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. ...
From $711 per night (USD)VRBO
From $1285 per night (USD)VRBO
4 Tropical Beach Oasis - Private Pool, Reef Charter Boating, Pets Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $1285 per night (USD)VRBO
From $903 per night (USD)VRBO
Making The Best Memories Along The Way! 3 Comfortable Units, Free Parking, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $903 per night (USD)VRBO
From $302 per night (USD)VRBO
Comfort and Convenience! Pets Allowed, Free Parking, Tennis Courts, Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $302 per night (USD)VRBO
From $964 per night (USD)VRBO
Your Beach & Marina Getaway - Boating, Pets & Sunsets Included - 3 Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $964 per night (USD)VRBO
From $602 per night (USD)VRBO
Florida Keys Escape! 2 Design Units, Pool, Tennis, Parking, Near Attractions
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $602 per night (USD)VRBO
From $322 per night (USD)VRBO
Look No Further! Free Parking, Pets Allowed, Onsite Pool, Near Seven Mile Bridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $322 per night (USD)VRBO
From $302 per night (USD)VRBO
Miles of Beach and Reef Await - Resort Comforts & Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $302 per night (USD)VRBO
From $302 per night (USD)VRBO
Your Relaxing Getaway Awaits! Pets Allowed, Onsite Pool, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $302 per night (USD)VRBO
From $1204 per night (USD)VRBO
Florida Keys Group Escape! 4 Classy Units, Free Parking, Outdoor Pool, Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $1204 per night (USD)VRBO
From $444 per night (USD)VRBO
Waterfront Key Colony Beach Home w\/ Golf Cart!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pets Welcome w/ Fee | Covered Patio | Canal Views & Access Dip in The Cabana Club's outdoor community pool or walk to t ...
From $444 per night (USD)VRBO
From $509 per night (USD)Expedia
Coastal Chic Getaway: Modern 2\/2 Condo in Key Largo, Marina, Pool, Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Please check out our other properties in Kawama Yacht Club, Ocean Point and Mariners Club by entering the following pro ...
From $509 per night (USD)Expedia
From $100 per night (USD)VRBO
Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience Cudjoe Key like a local in this charming 1-bedroom apartment. This nice property offers a cozy living room wi ...
From $100 per night (USD)VRBO
From $350 per night (USD)Expedia
Bimini Breeze - VO 313
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bimini Breeze - VO 313 Walk to Pool and Marina! Centrally Located Charming 2Bd/1Ba This home is located on a quiet circl ...
From $350 per night (USD)Expedia
From $383 per night (USD)VRBO
Tarpon Alley - Venture Out 509
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tarpon Alley - VO509 Canal Front35' Dockage Casually elegant, beautifully decorated, and fully stocked for your conveni ...
From $383 per night (USD)VRBO
From $1058 per night (USD)VRBO
Charming Bungalow Perfect for Families and Couples': Escape in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1058 per night (USD)VRBO
From $642 per night (USD)VRBO
Unwind at Your Own Oceanfront Haven - Resort Amenities, Pets Welcome - 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover the Florida Keys Resort lifestyle with tropical charm on the Gulf Coast. Explore Dolphin Research Center, Flori ...
From $642 per night (USD)VRBO
From $371 per night (USD)Expedia
Cozy home with private pool, BBQ, central AC, private dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Salty Air Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $371 per night (USD)Expedia
From $1779 per night (USD)VRBO
2 Family-friendly Units, Complimentary Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1779 per night (USD)VRBO
From $1074 per night (USD)VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1074 per night (USD)VRBO
From $836 per night (USD)VRBO
Florida Keys Getaway w\/ Stunning Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Whatever you imagine when you think of the Florida Keys, you'll find at this Layton vacation rental! Located just steps ...
From $836 per night (USD)VRBO
From $421 per night (USD)Expedia
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $421 per night (USD)Expedia
From $313 per night (USD)VRBO
Island Time Resort Condo #26, Island Time Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy Pool Resort with Tiki and Restaurant centrally located in Marathon, FL. A short drive to Sombrero beach. King maste ...
From $313 per night (USD)VRBO
From $508 per night (USD)Expedia
Changes In Latitude
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to coastal perfection at this upscale waterfront retreat in Key Haven, just minutes from Old Town Key West and Du ...
From $508 per night (USD)Expedia
From $496 per night (USD)VRBO
4 bed 2 bath\/ Hammer Point\/Professionally designed\/Seawall\/ Boat lift
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Canal Front Oasis in Hammer Point - Your Perfect Getaway Welcome to your dream vacation home in Hammer Point! This stun ...
From $496 per night (USD)VRBO
From $181 per night (USD)Expedia
Captain & Mermaid Diamond #BP25
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to this tropical sea-front retreat in Big Pine Key, a paradise just 30 miles from Key West. Surrounded by gem-lik ...
From $181 per night (USD)Expedia
From $388 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $388 per night (USD)VRBO
From $203 per night (USD)Expedia
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)Expedia
From $126 per night (USD)VRBO
Charming water front bungalow 40ft Dock & Tiki in the heart of Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the heart of the Florida Keys. Come relax, play, and stay in Key Largo. Our house is perfect for families &am ...
From $126 per night (USD)VRBO
From $263 per night (USD)Expedia
JUNE-AUG 2025 DISCOUNT - 2 Bedroom FL Keys Canal Home - Great Boating Access!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Pirates Quay! This newly remodeled 2 bedroom home in Little Torch Key is one of the nicest, most thought-out ...
From $263 per night (USD)Expedia
From $324 per night (USD)VRBO
2 Bedroom Canal Home in Cudjoe Key, FL w\/ Private Pool & Extra Loft Space
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Gecko House! This canal-front 2 bedroom, 2 bath house is located in a great boating area with easy access to ...
From $324 per night (USD)VRBO
From $371 per night (USD)Expedia
JULY 2025 DISCOUNT - 3 Bedroom\/2 Bath Canal Home w\/ Private Pool - Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Reel Life, a beautiful Cudjoe Gardens Oasis! Located on the ocean side of Cudjoe Key, this home has everythin ...
From $371 per night (USD)Expedia
From $562 per night (USD)VRBO
The Roost in Summerland Cove Isles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
The Roost in Summerland Cove Isles affectionately know as 'The Castle' is truly a gem nestled in a highly desirable neig ...
From $562 per night (USD)VRBO
From $405 per night (USD)Expedia
Sombrero Beach Tropical Getaway in the Heart of Marathon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the beauty of Marathon from this marvelous 1-bedroom condo. This tranquil retreat features a king bed in the be ...
From $405 per night (USD)Expedia
From $214 per night (USD)VRBO
Very Nice 2-bedroom Canal Home with a Concrete Dock in serene Big Pine Key, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Big Pine Breeze! Charming and tastefully decorated 2/2 home with beautiful sunset views from the large walk-a ...
From $214 per night (USD)VRBO
From $253 per night (USD)Expedia
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Marathon condo boasts 1 inviting bedroom. The living room features a cozy sofa bed for extra guests. Guests can enj ...
From $253 per night (USD)Expedia
From $215 per night (USD)VRBO
Amazing new 2-bedroom, 2-bathroom apartment in the heart of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Islamorada apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room also offers an extra queen ...
From $215 per night (USD)VRBO
From $590 per night (USD)Expedia
Spacious Key Largo Home with Dock with Fast Ocean Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your cozy getaway awaits in Key Largo at this gorgeous house. With 3 bedrooms including 1 king bed, 2 queen beds, 1 bunk ...
From $590 per night (USD)Expedia
From $628 per night (USD)VRBO
Canal front pool home in Florida key's Islamorada! Access to ocean w\/boat lift!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Luxury Waterfront Vacation Home in Islamorada Escape to paradise in this stunning waterfront vacation home located in t ...
From $628 per night (USD)VRBO
From $550 per night (USD)Expedia
Cozy home with outdoor shared pool, central AC, internet
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Villa del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $550 per night (USD)Expedia
From $192 per night (USD)VRBO
The Perfect Getaway is an upscale oasis for you and pets to relax and have fun!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Our stylish home will place you close to everything but provide comfort and relaxation for both people and pets alike. ...
From $192 per night (USD)VRBO
From $370 per night (USD)Expedia
Island Time at Ocean Pointe Luxe 2 King Spa BR\/BA, 2 Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: The excitement of America’s Caribbean, the Florida Keys, awaits you at Island Time! This designer decorated and ...
From $370 per night (USD)Expedia
From $527 per night (USD)VRBO
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $527 per night (USD)VRBO
From $769 per night (USD)Expedia
Sombrero Getaway: Poolside Retreat with Canal Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your tropical oasis in the heart of paradise! This spacious 4-bedroom, 3-bathroom vacation home is the perfec ...
From $769 per night (USD)Expedia
From $284 per night (USD)VRBO
Charming canal front with Ocean access 2-bedroom house in peaceful Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Tavernier, enjoy what this 2-bedroom, 2 bathrooms house has to offer. This perfect and peaceful retreat featu ...
From $284 per night (USD)VRBO
From $251 per night (USD)Expedia
Beautiful Home located in Downtown Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: Mango House 81212 Old Highway Islamorada, Florida Location: Ocean side located on the Old Road by Gree ...
From $251 per night (USD)Expedia
Click For PricingVRBO
Got Stress? You Need KeyBliss - The BEST Bayfront Unit in Buttonwood Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This beautiful end unit is nestled in the most charming area of the best condominium complex in Key Largo. As you walk u ...
Click For PricingVRBO
From $224 per night (USD)Expedia
Renovated waterfront duplex with canal access, deck, water views & central AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bohemian Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $224 per night (USD)Expedia
From $215 per night (USD)VRBO
Endless Summer Retreat: Dog-Friendly 3BR Canal Front Oasis, Dockage & Easy Atlantic\/Gulf Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $215 per night (USD)VRBO
From $433 per night (USD)Expedia
Open Water Modern Home 2\/2
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
RARE FIND OPEN WATER VIEWS FROM ALL ANGLES AND DECK! Located on Little Torch Key 28.5 mm Jolly Roger Estates. Meticulous ...
From $433 per night (USD)Expedia
From $888 per night (USD)VRBO
Sombrero Siesta: Heated Pool & Stunning Canal Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Sombrero Siesta, your ultimate tropical getaway in the heart of the Florida Keys! This luxurious canal-front ...
From $888 per night (USD)VRBO
From $224 per night (USD)Expedia
Water front 2-bedroom home in Key Largo with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Water front deep water canal 2 bedroom 1 bath comfortable and modern entire home in Key Largo. Parking for boat and trai ...
From $224 per night (USD)Expedia
From $637 per night (USD)VRBO
Walk to Beach: Waterfront Home in Marathon!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Kayaks & Paddleboard | Tropical Hut w/ Grill | Private Pool & Boat Dock | Pet Friendly w/ Fee Feel your worries drift a ...
From $637 per night (USD)VRBO
From $247 per night (USD)Expedia
Ocean Side Paradise Awaits!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic O ...
From $247 per night (USD)Expedia
From $263 per night (USD)VRBO
Ocean Isles Seaside Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to paradise! This new 1 bed/2 bath is centrally located in Marathon. The condo is steps away from open ocean vie ...
From $263 per night (USD)VRBO
From $465 per night (USD)Expedia
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $465 per night (USD)Expedia
From $244 per night (USD)VRBO
Florida Keys Marathon #211 Cozy waterfront 1 bdrm condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
You’re not in Florida, You’re in Paradise "The Keys", the American Caribbean! We are now accepting reservations for 2025 ...
From $244 per night (USD)VRBO
From $179 per night (USD)VRBO
Florida Keys Marathon #205 Cozy Waterfront 1-bedrm condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You’re not in Florida, You’re in Paradise "The Keys", the American Caribbean! We are now accepting reservations for 202 ...
From $179 per night (USD)VRBO
From $125 per night (USD)VRBO
Serene Key West Studio with Poolside Peace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)VRBO
From $376 per night (USD)Expedia
Ocean View Gem Ocean Pointe 3406 2BA\/2BR King\/Queen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Enjoy the ocean breeze from this beautiful top floor condo. This unique model has 2 balconies and is located on ...
From $376 per night (USD)Expedia
From $190 per night (USD)VRBO
Boater's Paradise ! Enjoy the sunsets from your covered patio...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Want to make a special arrangement? If you are a repeat customer, please contact me for special rates ! This tropical g ...
From $190 per night (USD)VRBO
From $660 per night (USD)Expedia
3-bedroom townhome in Key West with fitness room, WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $660 per night (USD)Expedia
From $951 per night (USD)VRBO
Ocean Paradise Point 12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this brand new, coastal modern 3-bedroom, 2.5-bathroom home located in a gated, intimate community right on th ...
From $951 per night (USD)VRBO
From $624 per night (USD)Expedia
Atlantis House Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled within the serene enclave of the Atlantis House Compound, the Palm and Banyan Suites offer a tropical oasis for ...
From $624 per night (USD)Expedia
From $728 per night (USD)VRBO
Coco's Poolside Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $728 per night (USD)VRBO
From $1558 per night (USD)Expedia
The Flower Power House - Boho Beautiful
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $1558 per night (USD)Expedia
From $694 per night (USD)VRBO
Paradise Palms~ Waterfront Oasis w\/ 40' Dock, Pool, Open Water Views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Property Highlights: • Sleeps: 8 • Bedrooms: 3 • Bathrooms: 3.5 • Parking: This property features 6-8 parking spaces fo ...
From $694 per night (USD)VRBO
From $4643 per night (USD)Expedia
**CASSIE’S PARADISE @ SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The vacation opportunity of a lifetime awaits at CASSIE’S PARADISE. A secluded oceanfront experience, this breathtaking ...
From $4643 per night (USD)Expedia
From $298 per night (USD)VRBO
VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a few houses off Duval on Virginia Street, VIRGINIA VISTA occupies the upper level of an almost 100-year-old home i ...
From $298 per night (USD)VRBO
From $296 per night (USD)VRBO
VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-ol ...
From $296 per night (USD)VRBO
From $1311 per night (USD)VRBO
A Luxury 5 Bedroom property\/Gorgeous bay views\/ Outdoor living and boat dockage in the heart of Marathon FL
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning 5-bedroom, 4.5-bathroom oasis offers the ideal blend of luxury, comfort, and outdoor fun. The main house f ...
From $1311 per night (USD)VRBO
From $265 per night (USD)Expedia
4 bed 2 bath\/Canal front\/Dockage\/ Port Largo
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your dream getaway in the heart of Key Largo! This beautifully renovated 4-bedroom, 2-bathroom home offers a ...
From $265 per night (USD)Expedia
From $222 per night (USD)VRBO
Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf\/Atlantic Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
County zoning regulations require a minimum rental period of 28 nights, and no exceptions can be made. Please review add ...
From $222 per night (USD)VRBO
From $293 per night (USD)Expedia
Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Garden of Roses | Private Hot Tub, Prime Key West Location! Experience the essence of Key West living at Garden of Rose ...
From $293 per night (USD)Expedia
From $911 per night (USD)VRBO
Casa Cayo: 4 bedroom home with pool and dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Casa Cayo, a luxurious vacation rental in Coco Plum! The home includes two identical master suites with en-s ...
From $911 per night (USD)VRBO
From $220 per night (USD)Expedia
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $220 per night (USD)Expedia
From $439 per night (USD)VRBO
Ritaville | New! Waterfront Paradise with Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Ritaville | New! Waterfront Paradise with Private Pool Experience a serene retreat at Ritaville, a stunning waterfront ...
From $439 per night (USD)VRBO
From $263 per night (USD)Expedia
Key West vibes, 2-bedroom townhome with AC, WiFi in marvelous Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Key West, this delightful townhome boasts 2 bedrooms with a king bed and a full bed, perfect for a small grou ...
From $263 per night (USD)Expedia
From $486 per night (USD)VRBO
The Salty Seahorse- Pristine Private Pool, Game Room & Cabana Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Salty Seahorse Time to relax at this modern coastal 3 bedroom, 3 bathroom duplex with 25 ft of boat dockage and a beau ...
From $486 per night (USD)VRBO
From $299 per night (USD)VRBO
Paradise away from home.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious paradise features a large living area with windows that flood the space with natural light, while the kitc ...
From $299 per night (USD)VRBO