
Vacation rentals in Monroe County
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Top-rated vacation rentals in Monroe County
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Enjoy our Beautiful Home on a Fun Canal! Hot tub!
Beautiful & Modern 4/3 Canal House! completely renovated. Go Kayaking through the Canals.. Enjoy the views of the backyard and canal with jumping fish all day, House is in a centric and quiet neighborhood. Amazing backyard & terrace with a BBQ, 2 Kayaks provided for Guest. Home is near nice restaurants and close to main Highways.. ✔️15min from Miami International airport ✔️25min - Downtown Miami ✔️ 30min - Miami Beach ✔️10-15min - Dadeland Mall & Merrick Park Come Relax at our Paradise Home!
4.93 out of 5 average rating, 249 reviews
Beach House, Private Pool, Dock, Gulf View Sunsets
You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.
4.93 out of 5 average rating, 81 reviews
Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.
4.93 out of 5 average rating, 153 reviews
Tiny Home Aqua Lodges 2/1
This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.
4.76 out of 5 average rating, 157 reviews
| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport
Discover the magic of Miami at our stunning 4BR/3BA modern retreat in vibrant Little Havana’s west side! This spacious, open-concept home sleeps up to 11 and features a sleek living room, fully stocked kitchen with stainless steel appliances, dinnerware, wine/shot glasses, cookware, tabletop appliances & complimentary coffee. The highlight? A resort-style backyard with a pool, mini golf, life-size chess, cornhole, Connect Four, outdoor pool table, a covered gazebo & deluxe grill/hibachi!
4.94 out of 5 average rating, 128 reviews
Miami Sanctuary | Heated Saltwater Pool & BBQ
Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area
5.0 out of 5 average rating, 494 reviews
Villa Paradise | 17 PPL | Pool | BBQ | Game Room
Welcome to Villa Paradise! - Private Patio: Pool, BBQ, Fire pit & Outside furniture - Game Room: Pool & Ping Pong Table, Foosball table & TV - 17 PPL (1 KING, 5 QUEEN, 2 full, 1 twin) - 13 min to Miami Executive Airport - WIFI & Dedicated work space - Fully equipped kitchen - Free parking - Safe neighborhood - Washer & Dryer in unit - Kids friendly & Travel Crib - Beach towels - Self check in - Amazing guidebooks & Hosts available 24/7 Text us any questions! We would love to host you!
4.88 out of 5 average rating, 102 reviews
Flakey's
Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.
4.97 out of 5 average rating, 219 reviews
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.
4.93 out of 5 average rating, 394 reviews
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace
5.0 out of 5 average rating, 6 reviews
Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.
4.96 out of 5 average rating, 212 reviews
Eva | 12 ppl HOT Pool |Top Location | Piano | Golf
Renovated family home with 5 bedrooms and 4 full bathrooms. Heated pool year-round, mini golf, BBQ area and swing. Modern design with piano and Smart TVs. Parking for 5 cars. Prime location near airport, beaches and nightlife. Sleeps up to 16: 1 king, 2 queen, 2 full, 2 twin and 2 sofa beds (full & queen). Please confirm total guests. Add pets to reservation. Notify us if traveling with children for pool fence.
4.98 out of 5 average rating, 134 reviewsPopular amenities for Monroe County vacation rentals
Other great vacation rentals in Monroe County

Waterfront Pool Home w/ Private Dock, Tiki Hut & B
5.0 out of 5 average rating, 4 reviews
Lakeview Retreat • 15 Min to MIA • Pool_Spa
New place to stay
Perfect escape to the ocean
4.79 out of 5 average rating, 67 reviews
Gorgeous Ocean View Home!
4.86 out of 5 average rating, 99 reviews
Key West Outpost: eco-vacation
4.95 out of 5 average rating, 84 reviews
Heated Pool Oasis • 12 Guests •Midway Keys & Miami
4.97 out of 5 average rating, 38 reviews
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
4.98 out of 5 average rating, 41 reviews
Private Dock| 5min beach| Kayak| Sunset view|RV
4.91 out of 5 average rating, 35 reviewsDestinations to explore
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Coral Castle
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Theater of the Sea
- Key Largo Kampground And Marina
- Ernest F. Coe Visitor Center
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Founder's Park
- Monkey Jungle
- History Of Diving Museum
- Homestead Bayfront Park
- Everglades Safari Park
- Calusa Campground
- Conch Key
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