Ski-in/Ski-out holiday rentals in Monroe County

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Top-rated ski-in/out rentals in Monroe County

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Guest favourite

A beachfront view showcases a modern two-story condo building with large glass doors, situated on a white sand beach. The gentle waves lap at the shore, and palm trees provide some shade, enhancing the serene coastal environment.

Home in Florida Keys

4.9 out of 5 average rating, 29 reviews

Beach Breeze

Be one of the first guest to stay at our new condo on the rare white sand private beach located in Key Colony Beach, FL. 2+2 ensuite, gourmet kitchen with designer touches. Patio table & chairs for outdoor dining and new Wicker upscale love seat & 2 chairs. Stackable washer & dryer in every unit. TV in living, primary & guest rooms. Paddle board, Kayak or swim right off of the beach or just sit and enjoy the beautiful view of the water. Pool is open. Minimum 7 days rental City Code.

Apartment in Downtown Miami

W Hotel & ICON | Water & City Views | 20th Floor |

Discover urban luxury in ICON Brickell, one of Miami's premier buildings! Marvel at expansive city views from our home's open layout. 🚶‍♂️ Steps away from Brickell City Center. 🚉 Easy access to Metrorail/Metromover; just a block from I-95. 🏠 Features include in-unit washer & dryer. 🏊‍♂️ Enjoy exclusive building amenities: a stunning heated swimming pool, open-air pool deck, club room, and a state-of-the-art fitness center. Perfect for exploring the heart of Miami!

A modern living space featuring a white sectional sofa and a round dining table with four gold chairs. Large windows allow natural light, revealing a stylish decor with framed artworks. A patterned rug lies under the table, complementing the light tile flooring.

Apartment in Downtown Miami

4.63 out of 5 average rating, 111 reviews

CHIC Ocean View 2BR/1BA | ICON Brickell #2509

*The balconies will be closed due to the HOA façade renovation project* Stylish high-floor unit with beautiful views, as shown in the photos. This is not a full 2 bed/2 bath—it’s 1 bedroom + den and 1 bath. The den has a door for privacy but no window and shares the bathroom with the master. Only 2 guests can access amenities (non-transferable); minors not counted. Located in Icon Brickell, shared with the W Hotel, enjoy resort-style amenities like a large pool and dining.

A covered outdoor seating area features modern furniture arranged on a tiled patio. A small table is situated at the center, surrounded by comfortable chairs. Decorative plants and soft lighting create a relaxed atmosphere, inviting guests to enjoy the space.

Home in Little Havana

4.27 out of 5 average rating, 15 reviews

VERY CLOSE, Airport, port, Downtown, Beach Wynwood

👋 Welcome to Miami! 🏡 Spacious and remodeled house in the heart of Miami, in front of the Marlins stadium ⚾. 3 bedrooms, 2 bathrooms, 6 beds, sofa, queen size inflatable mattress, double mattress and a single mattress. Large patio with barbecue 🍖 ideal for groups/families. Quick access to the highway 🚗. 5 minutes from Downtown, Brickell, airport ✈️, port 🛳️ and water park💦. 15 min from South Beach 🏖️.

A cozy sleeping area features a spacious bed made with white bedding, accented by dark throw pillows. Nightstands with lamps on either side provide additional lighting. Soft wood flooring complements the simple decor, and a small plant adds a touch of greenery.

Private room in Little Havana

5.0 out of 5 average rating, 5 reviews

Overlooking Miami Downtown,Room private & restroom

Enjoy the simplicity of this quiet and centrally located accommodation with a spectacular panoramic view of Downtown Miami, Brickell Financial District and Miami Beach 🏖, in the heart of Little Havana near the famous Calle 8 for dining and salsa dancing 💃🏻 and Latin rhythms.

A comfortable living area features a plush sofa and a small white coffee table. Shelves filled with books stand against the wall, while natural light streams in through large glass doors. Soft lighting is provided by a lamp on the side table.

Flat in Big Pine Key

Sir David Waterfront

Located off US1 on Big Pine Key Waterfront canal. Peaceful , trendy townhome. Perfect for couples looking for some R&R and in an upscale peaceful townhome. . 20 min to Key West. Take a swim in the canal or rent a boat or jet skis and enjoy some tranquility.

A cozy sleeping area features a sleek dark wood bed with light-patterned pillows. A soft throw is neatly placed at the foot of the bed. A bedside table with a lamp stands nearby, providing gentle illumination, while a window with blinds offers natural light.

Private room in Coral Way

4.5 out of 5 average rating, 6 reviews

Coral Way Miami Private Room

Our house is very central well located just 5 minutes from Key byscaine, 15 minutes from the Airport. 15 minutes from South Beach and 1 min from La Coral Way where you can walk and enjoy a day of shopping or eating at the restaurants of this famous Ave.