Holiday rentals with a pool in Monroe County

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.

Private Paradise between Miami & the Keys

My 4/3 home is in the area known as the "Gateway to the Keys". Enjoy a comfortable stay for 10 people in 4 bed rooms. Great place for families & travelers. Very comfy home, & the back yard has the feel of a true tropical paradise. Good WIFI. NO ADDITIONAL GUESTS & NO DJs. NO PARTIES. I RESERVE THE RIGHT TO ENTER THE HOME IF I FEEL THERE IS AN UNAUTHORIZED PARTY/EVENT. FINES WILL BE APPLIED FOR NOISE VIOLATIONS. We do not allow parties. UNAUTHORIZED parties can/will result in a $500 fine.

Feels Like Summer ~ Panoramic Water Views! 2BR

Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Feels Like Summer! is the ultimate retreat. Enjoy incredible panoramic water Biscayne Bay views that will leave you in awe. With South Miami Beach 3 miles away you can take in the sun of Miami Beach, while still feeling the energy of downtown Miami. It's the best of both worlds, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

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.

Brickell Oasis: Pool, Spacious, Stylish

-Less than 5 minutes to the heart of Brickell (closest you can get with a house) -Easy access to South Beach, Wynwood, Midtown, Coral Gables (all within 10-15 minutes) -Newly renovated with stylish, high-end finishes. Notably two rooms have their own bathrooms, so its a comfortable setup for large groups. -Backyard pool and patio area feels like an oasis. Great place to hangout with friends, grill, or just relax and enjoy the greenery, the sun during the day, and the stars at night.

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Beach House Paradise 6 BR Suites Pool & Heater

Resort-Style Beach House Paradise – 6BR Luxury Home w/ Heated Pool, Jacuzzi, 100 FT Dock, fishing station & 700 square feet Game Room. Brand-new 2025 luxury retreat in the heart of Marathon! Stunning 6 Bedroom Master Suites each with its own private bathroom and closet, plus an additional half bathroom for guests. home offers high-end comfort, space, and entertainment. Perfect for large families or groups. Fisherman paradise with commercial ice-machine. Lic # VACA-25-59

Lakefront private house paradise

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. 28 days minimum rental Whether you're seeking a peaceful retreat or an adventure-filled getaway, this lake house provides the best of both worlds.

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views