House holiday rentals in Monroe County

4.93 out of 5 average rating, 145 reviews

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

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.

4.98 out of 5 average rating, 105 reviews

Oasis&Art/ArtificialBeach/HeatedPool/MiniGolf

House in Miami, Sleeps 12 Heated Pool/Mini Golf/Kids Playground/BBQ/Cornhole game/Small beach/mini football Ned/Hammocks. Peace, nature, fun and more you will find in our house. The house is decorated with unique original art. Don't miss out on this newly remodeled cozy home, an ideal retreat for a peaceful and rejuvenating vacation. With a spacious living room, dining area, and a fully equipped kitchen, this house has everything you need. Nestled in a secure and tranquil neighborhood.

A modern living room showcases marble accents and a large wall-mounted flat screen TV. A plush sectional sofa with bold black and white patterns is arranged around a decorative coffee table. Natural light filters through the window with minimalistic blinds.

4.96 out of 5 average rating, 108 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!

A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.

5 out of 5 average rating, 468 reviews

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

4.97 out of 5 average rating, 215 reviews

The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

Home in Islamorada

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, 31 reviews

Home in Summerland Key

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!

Superhost

4.9 out of 5 average rating, 102 reviews

Luxury Stay w/ Heated Pool, Golf & Chess Yard

☀️ Enjoy the perfect vacation in the City of the Sun! ☀️ This spacious 4-bedroom, 4-bathroom home is located just minutes from the airport, top restaurants, bars, shops, and Miami’s main attractions. Ideal for families and groups, the property features a large backyard designed for entertainment: refreshing pool, mini beach, fire pit, golf putting area, and giant chess. Every corner is crafted for relaxation, fun, and unforgettable memories. Come live your best Miami experience! 🌴

4.83 out of 5 average rating, 111 reviews

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Superhost

4.89 out of 5 average rating, 74 reviews

Lakefront Lux Home • Pool_Spa_BBQ, Games & Fun

Lake/Heated Pool/Jacuzzi/Play Ground/Mini Golf/Ping Pong table/Hammock/BBQ area/Basketball hoop/Volleyball/Badminton/Kayak/Fire Pit/Arcade Game/Pool Table/Foosball Welcome to Your Dream Getaway! Experience the perfect blend of modern luxury and natural beauty at our newly renovated lakeside retreat. With a spectacular design that exudes comfort and style Book now and make unforgettable memories in a home that's as inviting as it is beautiful.

4.96 out of 5 average rating, 68 reviews

The exterior of a charming lakefront retreat is displayed, featuring a private heated pool, green turf, and white Adirondack chairs arranged on a sandy area by the water's edge. A covered balcony offers shaded seating, with colorful twilight skies creating a serene backdrop.

Home in Key Largo

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.

4.95 out of 5 average rating, 107 reviews

Home in Marathon

4BR 3B, Heated Pool & Spa, 60' Dock

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

A modern exterior of the house showcases a private pool with a surrounding patio featuring loungers. Tall, elegant arches and windows allow for ample natural light, while tropical leaves in the foreground add a vibrant touch to the inviting outdoor space.