
Vacation rentals in Monroe County
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Top-rated vacation rentals in Monroe County
Guests agree: these stays are highly rated for location, cleanliness, and more.

Make It Happen! Brand New with Amazing Water Views
Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Make It Happen! is the ultimate retreat, equipped with everything you could need. Enjoy views of Biscayne Bay and Margaret Pace Park that will leave you in awe. With South Miami Beach 3 miles away you can indulge in the sun of Miami Beach while still feeling the energy of downtown Miami, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

Island Sanctuary Islamorada
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Stay on Roxie - free transport & snacks, BYOB.
Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Waterfront Sunsets, Great Price, Relaxing Spot!!!
Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg
Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Amazing houseboat with 2nd floor observation deck
Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Lighthouse - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!
Popular amenities for Monroe County vacation rentals
Other great vacation rentals in Monroe County

Coastal Oasis #44 Key Largo 4BR Villa | Partial

Marathon Keys Escape • Pool • Hot Tub • Near Beach

b watervibe

Viamarhe Cabin-Private beach, Kayak, yard games

Chiquita Waterfront Canal Home

NEW! 4-Story Villa, Private Rooftop, Pool, Marina

Oceanfront 3-Story Luxury, Dockage, Gameroom

Grand Blue/120'Dock/HtdPool/GameRoom/BBQ/BabyItems
Destinations to explore
- Campsite rentals Monroe County
- Beachfront rentals Monroe County
- Apartment rentals Monroe County
- Cottage rentals Monroe County
- Family-friendly rentals Monroe County
- Rentals with a kayak Monroe County
- Rentals with an accessible height toilet Monroe County
- Townhouse rentals Monroe County
- Rentals with a home theater Monroe County
- Resort rentals Monroe County
- Waterfront rentals Monroe County
- Rentals with a hot tub Monroe County
- Pet-friendly rentals Monroe County
- Private suite rentals Monroe County
- Rentals with a fireplace Monroe County
- Tiny house rentals Monroe County
- Serviced apartment rentals Monroe County
- Rentals with an EV charger Monroe County
- Villa rentals Monroe County
- Hostel rentals Monroe County
- Bed and breakfasts Monroe County
- Rentals with lake access Monroe County
- Rentals with outdoor seating Monroe County
- Rentals with breakfast Monroe County
- Rentals with a patio Monroe County
- Farmstay rentals Monroe County
- Condo rentals Monroe County
- Rentals with beach access Monroe County
- Rentals with a washer and dryer Monroe County
- Luxury rentals Monroe County
- Ski-in/ski-out rentals Monroe County
- Rentals with an accessible height bed Monroe County
- Aparthotel rentals Monroe County
- Loft rentals Monroe County
- Boat rentals Monroe County
- Guesthouse rentals Monroe County
- House rentals Monroe County
- Rentals with pools Monroe County
- Hotel rooms Monroe County
- Rentals with a fire pit Monroe County
- Smoking-friendly rentals Monroe County
- RV rentals Monroe County
- Vacation home rentals Monroe County
- Rentals with a sauna Monroe County
- Houseboat rentals Monroe County
- Fitness-friendly rentals Monroe County
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Coral Castle
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Far Beach
- Sea Oats Beach
- Everglades Alligator Farm
- Conch Key
- Theater of the Sea
- Monkey Jungle
- Long Key State Park
- Horseshoe Beach
- EAA Air Museum
- Schnebly Redland's Winery & Brewery
- Long Beach
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Sandspur Beach
- Highland Beach
- Keys' Meads
- Things to do Monroe County
- Food and drink Monroe County
- Nature and outdoors Monroe County
- Sports activities Monroe County
- Sightseeing Monroe County
- Entertainment Monroe County
- Tours Monroe County
- Art and culture Monroe County
- Things to do Florida
- Sightseeing Florida
- Wellness Florida
- Nature and outdoors Florida
- Tours Florida
- Sports activities Florida
- Art and culture Florida
- Food and drink Florida
- Entertainment Florida
- Things to do United States
- Food and drink United States
- Tours United States
- Entertainment United States
- Wellness United States
- Nature and outdoors United States
- Art and culture United States
- Sightseeing United States
- Sports activities United States




