House holiday rentals in Monroe County

4.95 out of 5 average rating, 368 reviews

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

4.91 out of 5 average rating, 171 reviews

A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.

Home in Key Largo

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

A private pool area is surrounded by lush greenery, featuring a mosaic-tiled pool reflecting vibrant colors in the water. Two woven lounge chairs are positioned nearby, inviting relaxation. The sky showcases a blend of warm colors at sunset, enhancing the serene outdoor setting.

4.96 out of 5 average rating, 102 reviews

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ

Welcome to Jessica and Javier House in Miami! We want to Be your Hosts ! Let us show you why you should book with us: - 2000 ft2 ground floor house - 3BDR Designed for 12 guests - 5 Min to Zoo - 20 Min to Coral Gables and Little Havana - 25 Min to Beach - 30 Min to Miami Airport - Residential Area - Private Pool - Spa - Fast WIFI - Fully equipped kitchen - Dedicated work space - Free Onsite parking - BBQ - Outside dining - Washer & Dryer - Kids and Pet friendly - 2 Sofa beds - Family games

4.93 out of 5 average rating, 119 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.

A serene lakeside view features lounge chairs placed on sandy shores, framed by palm trees. A kayak rests nearby, with the crystal clear water reflecting shades of blue and aqua. The peaceful scene invites relaxation under the bright sky.

4.95 out of 5 average rating, 168 reviews

Modern Beach Lake-Front House in Miami !

Welcome to our stunning 5/4 beachfront lake house! This newly renovated property offers the perfect blend of modern amenities and natural beauty. Located in a central and peaceful neighborhood, guests can enjoy a range of water activities such as kayaking, paddle boarding, and swimming while taking in the views of the Blue lake. Seeking relaxation or adventure, this home has something for everyone.. ✔️15min from Miami International airport ✔️25min to Downtown Miami ✔️30min from Miami Beach

4.99 out of 5 average rating, 209 reviews

A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.

Home in Key Largo

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!!!

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.

4.99 out of 5 average rating, 390 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

Superhost

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

Home in Upper Sugarloaf Key

4.94 out of 5 average rating, 105 reviews

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.

4.92 out of 5 average rating, 211 reviews

An aerial view of the waterfront area shows vibrant turquoise waters and lush greenery. The scene includes several residential buildings along the coastline and a nearby marina, with boats visible on the water and the horizon illustrating a scenic expanse.

Home in Marathon

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

4.99 out of 5 average rating, 102 reviews

A cascading waterfall flows over natural stone ledges, creating gentle sounds. Vibrant pink bougainvillea blooms are prominently featured alongside the rocks, adding a touch of color to the tranquil setting.

Home in Coral Gables

Casa Cascada in Coral Gables Area

Welcome to Casa Cascada - in the heart of Coral Gables. Where you are 3 miles from Miami International Airport, close to Miracle Mile, Little Havana, South Beach and some of the best restaurants and shopping in Miami. Come and stay a while where the vibe is eclectic and inspiring, yet the most relaxing. Enjoy any one of our four open concept bedrooms — or relax in our personal favorite space, the backyard. Where the sound of the waterfall soothes your soul.

4.97 out of 5 average rating, 126 reviews

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

Home in Marathon

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

A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.