
Holiday houses in Monroe County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Monroe County
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Blue Diamond | 7 PPL| Pool | 5 mins NU Stadium|BBQ
Welcome to Blue Diamond Villa, a luxury home in Miami! - Pool - Top Location - 5 mins to Miami International Airport - 7 mins to NU Stadium - 10 mins to Coral Gables - 20 mins to Miami Beach - Stunning view from Master Bedroom - BBQ, TV & Outside furniture - 7 PPL (1 KING, 1 QUEEN BUNK BED & 1 TWIN) - Washer & Dryer - Kids friendly & Travel Crib - Private Patio - Dedicated Workspace - WIFI - Fully equipped kitchen - Free parking - Safe neighborhood - Self-check in - Hosts available 24/7

Sanctuary Salt water heated pool BBQ Grill Oasis
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

My Little Oasis2 Waterfront Retreat, Key Largo
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.

Starlight Serenity - Hideaway with Stunning Views
Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

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.

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!

Lakefront pool house, jacuzzi Beachfront
Serene Lakefront Retreat – Your Perfect Getaway! Escape to paradise in this beautiful lakefront home , offering breathtaking water views, and a relaxing atmosphere. Nestled in a tranquil neighborhood, this home is perfect for families, couples, or friends looking to unwind and enjoy Florida’s natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled getaway, this lake house provides the best of both worlds.

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.

Tiki Suites ~ Original Tiki ~ Floating Bungalows
Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

Wake Up On The Water | Luxury Marina | Key West
Wake up to the rhythm of the water and experience Key West from a completely different perspective. Stay aboard a 45-ft sailing yacht at the Perry Hotel & Marina. Enjoy 2 pools, gym, fine dining, and a free shuttle to Old Town. Ideal for couples or close knit groups: intimate, memorable, and all part of the yacht lifestyle.

Modern Downtown Studio | Walk to Kaseya Center
"Perfect location with lovely people." This studio residence offers a seamless stay in Downtown Miami. You are just a 2-minute walk from Bayfront Park and a 3-minute walk to Kaseya Center. Our apartment is built for solo travelers seeking a peaceful, functional base for short stays or temporary housing.
Popular amenities for Monroe County holiday rentals
Other great holiday rentals in Monroe County

Best Location in Marathon & KCB!

Family Oasis: Pool, Spa, Sauna + Kids Play Area

Villa Gaviota

Lakefront Lux Home • Pool_Spa_BBQ, Games & Fun

b watervibe

Heated Pool Oasis • 12 Guests •Midway Keys & Miami

Lagoona-Matata

Beach House, Private Pool, Dock, Gulf View Sunsets
Destinations to explore
- Smoking-friendly rentals Monroe County
- Rentals with a home theatre Monroe County
- Resort rentals Monroe County
- Bed and breakfasts Monroe County
- Serviced apartment rentals Monroe County
- Villa rentals Monroe County
- Loft rentals Monroe County
- Rentals with a patio Monroe County
- Rentals with an EV charger Monroe County
- Beachfront rentals Monroe County
- Rentals with breakfast Monroe County
- Rentals with a hot tub Monroe County
- Pet-friendly rentals Monroe County
- Private suite rentals Monroe County
- Condo rentals Monroe County
- Houseboat rentals Monroe County
- Rentals with a kayak Monroe County
- Rentals with lake access Monroe County
- Rentals with an accessible height toilet Monroe County
- Rentals with an accessible height bed Monroe County
- Boat rentals Monroe County
- Guesthouse rentals Monroe County
- Hotel rooms Monroe County
- House rentals Monroe County
- Bungalow rentals Monroe County
- Boutique hotels Monroe County
- Rentals with a washing machine and dryer Monroe County
- Cottage rentals Monroe County
- Rentals with a fireplace Monroe County
- Apartment rentals Monroe County
- Family-friendly rentals Monroe County
- Rentals with pools Monroe County
- Tiny house rentals Monroe County
- Ski-in/ski-out rentals Monroe County
- Rentals with a fire pit Monroe County
- Campsite rentals Monroe County
- Aparthotel rentals Monroe County
- Rentals with outdoor seating Monroe County
- Waterfront rentals Monroe County
- Townhouse rentals Monroe County
- Rentals with a sauna Monroe County
- Rentals with beach access Monroe County
- Luxury rentals Monroe County
- Fitness-friendly rentals Monroe County
- Farmstay rentals Monroe County
- RV rentals Monroe County
- Holiday home rentals Monroe County
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Schnebly Redland's Winery & Brewery
- Calusa Campground
- Coral Castle
- Homestead-Miami Speedway
- Bahia Honda State Park
- Robbies Marina Of Islamorada
- Theater of the Sea
- Seven Mile Bridge
- Everglades Alligator Farm
- Ernest F. Coe Visitor Center
- Key Largo Kampground And Marina
- Monkey Jungle
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Founder's Park
- History Of Diving Museum
- Conch Key
- Homestead Bayfront Park
- Everglades Safari Park
- Things to do Monroe County
- Sightseeing Monroe County
- Entertainment Monroe County
- Art and culture Monroe County
- Tours Monroe County
- Food and drink Monroe County
- Nature and outdoors Monroe County
- Sports activities Monroe County
- Things to do Florida
- Wellness Florida
- Art and culture Florida
- Tours Florida
- Entertainment Florida
- Sightseeing Florida
- Food and drink Florida
- Sports activities Florida
- Nature and outdoors Florida
- Things to do United States
- Food and drink United States
- Nature and outdoors United States
- Sightseeing United States
- Tours United States
- Entertainment United States
- Art and culture United States
- Sports activities United States
- Wellness United States





