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Holiday rentals in Monroe County

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Top-rated holiday rentals in Monroe County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A wide balcony overlooks a serene harbor, featuring several boats docked in the water. Two tall chairs are positioned against the railing, offering a view of the vibrant blue sky and surrounding marina.
Home in Key Largo
4.98 out of 5 average rating, 229 reviews

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!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Guest favourite
A rooftop pool area is showcased, featuring a shimmering blue pool surrounded by orange lounge chairs. A white umbrella provides shade to one section. In the background, expansive views of the bay and a clear blue sky are visible, enhancing the serene atmosphere.
Flat in Miami
4.9 out of 5 average rating, 223 reviews

Stunning Studio w/Bay & City View Free Park/Pool

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

Top guest favourite
Guest house in Miami
4.99 out of 5 average rating, 111 reviews

Casa Palma Guesthouse with Private Patio & Garden

Make your Miami stay peaceful and memorable at Casa Palma, a centrally located guesthouse minutes away from the best of Miami! Great restaurants, wine shop and a supermarket in walking distance. Free and very close-by Coral Way trolley line takes you to Coral Gables, Brickell, downtown and Port of Miami cruise hub. Close drives to Little Havana, Coconut Grove, Coral Gables & Brickell. Easy 15-20 minute drives to Miami International Airport, Wynwood, South Beach or lovely Key Biscayne beaches.

Top guest favourite
A wooden dock extends over calm waters, flanked by white pilings and gently swaying palm trees. The warm hues of twilight fill the sky, reflecting softly on the water's surface, creating a serene atmosphere perfect for evening relaxation.
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 126 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Guest favourite
Guest house in Key Largo
4.85 out of 5 average rating, 491 reviews

Romantic cozy peaceful Guesthouse beach Sunsets.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

Guest favourite
A bright guest room features large arched windows with sheer curtains allowing soft light to illuminate the space. A spacious bed with light bedding is centered in the room, complemented by a wooden table and a chair. A ceiling fan is visible above.
Guest suite in Miami
4.89 out of 5 average rating, 245 reviews

Quiet Guest Suite, Private Entrance, Patio+Parking

Take it easy at this unique and tranquil getaway in our 1930's Spanish Villa in the center of Little Havana and Coral Gables in the heart of Shenandoah. Your Guest Suite is equipped with a private entrance, private garden, and parking. Casita Amorcita is designed to give you the feeling of 'home' and 'love,' with the guest experience in mind. All linens are 100% cotton. Here you will have all that you need to rest, recover, recharge, and enjoy. We look forward to welcoming you home.

Top guest favourite
A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.
Boat in Islamorada
4.93 out of 5 average rating, 372 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.

Guest favourite
Houseboat in Key West
4.94 out of 5 average rating, 159 reviews

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Guest favourite
A modern two-story residence is shown, featuring a neutral façade of light and dark materials. Large windows are visible on the upper level, and a sleek garage door is positioned on the right. A minimalist landscape design includes young trees and a scooter parked on the driveway.
Guest house in Florida City
4.98 out of 5 average rating, 124 reviews

Luxury Loft

Kick back and relax in this calm, stylish space. A private suite with your own entrance, your personal parking space and no shared space with others! Safe neighborhood close to the Florida Keys, Outlet mall, Miami, the Everglades and so much more. Equipped with all the essential to make your stay comfortable. Just 3 minutes away from Walmart, 25 minute drive to the Keys & 27 to Miami! Nearby Everglades (5 min ) Key Largo (30 min) Miami (20 min) Hospital ( 10 min)

Superhost
A spacious studio is presented, featuring a king-size bed with soft linens and decorative pillows. Two windows allow natural light to illuminate the room, complemented by a yellow accent chair and various indoor plants. A small table with a bottle of wine and glasses enhances the setting.
Flat in Miami
4.85 out of 5 average rating, 312 reviews

King Bed Comfort – 5 Mins to Miami Hotspots

- TOTALLY PRIVATE BEAUTIFUL STUDIO Beautiful studio near everything!!! 5 minutes from the Airpot, Wynwood, Design District, South Beach, Port, Brickell, AAA, - King Size Bed - Private parking -Fully stocked kitchen also wifi, Smart Tv - 6 star hospitality - Washer and Dryer on premises to use for free - Property is 1 of 4 Airbnb on the property -$100 Pet fee -per stay. -NOTE: two pets, would be $150 per stay ( not apply for long-term stays)

Top guest favourite
Guest suite in Homestead
5 out of 5 average rating, 178 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Guest favourite
Barn in Homestead
4.9 out of 5 average rating, 229 reviews

The Glamping Barn - on a beautiful 5 acre farm!

When you come and stay with us, it’s a deeply immersive experience with our horses and chickens. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

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