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

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

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

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Top guest favorite

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 KEY COL BCH

4.95 out of 5 average rating, 20 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.

Guest favorite

A modern single-family house is displayed with a bright yellow exterior. A white pergola extends over the front porch, providing shade. Lush tropical plants add greenery to the landscape, while clear blue skies create a vibrant background.

Home in Marathon

4.92 out of 5 average rating, 12 reviews

Keys Escape - It's 5 o'clock

A modern 3 bedroom / 4 full bathroom single family house with a pool and dock and spectacular water views! Easily sleeps 8 people. First level of the property will contain the living room, dining and kitchen. This home boasts numerous at-home dining options, with a large indoor dining table for 8, cozy balcony seating; perfect for morning coffee or afternoon cocktails, and a Cabana for casual poolside dining. Pull your boat up to the dock and jump in the salt water pool to cool off.

Superhost

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.

Condo in Miami

4.77 out of 5 average rating, 97 reviews

CHIC Ocean View 2BR/1BA | ICON Brickell

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. Kitchen features Wolf and Sub-Zero appliances. Steps from Brickell’s top spots.

Superhost

Apartment in Cutler Bay

New place to stay

Bay Nest Hideaway | Private Lux 1BR Near It All

Bay Nest is a peaceful, centrally-located private 1BD/1BA LUX Apartment in Miami, perfect for couples, solo travelers, and business guests. Enjoy a quiet retreat with a private entrance, fast Wi-Fi, comfortable bed, and a clean, stylish space ideal for relaxing or remote work. Conveniently located near major highways, shopping, dining, beaches, and local attractions, Bay Nest offers easy access to everything while providing a calm, home-like stay.

An open-concept living space features a modern kitchen with stainless steel appliances and a dining area with a glass table. Large windows provide views of the city and sky, while a white sofa complements the neutral color palette. Decorative plants add a touch of greenery.

Apartment in Miami

Spectacular sunsets 2/2 downtown

.Fully furnished and equipped 2 bed/2 bath in the heart of downtown with sunset and city views. Beautifully designer decorated, just bring your suitcase! Amenities include: fitness center, infinity pools, business center, playroom, racketball, bbq area, valet, concierge, media room and more. One assigned parking space. Walking distance to Brickell City Center, 8 min to the beach. Great restaurants and just steps away from the MetroMover station

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 Miami

3.33 out of 5 average rating, 3 reviews

VERY CLOSE, Airport, port, Downtown,Beach Wynwood

👋 Bienvenido a Miami! 🏡 Casa amplia y remodelada en el corazón de Miami, frente al estadio de los Marlins ⚾. 3 habitaciones, 2 baños, 6 camas, sofá, colchón inflable queen, colchón matrimonial y uno individual. Patio grande con barbacoa 🍖 ideal para grupos/familias . Acceso rápido a la autopista 🚗. A 5 min de Downtown, Brickell, aeropuerto ✈️, puerto 🛳️ y parque acuático 💦. A 15 min de South Beach 🏖️.

Apartment in Miami

New place to stay

Icon Brickell | 1BR Modern Condo

Enjoy a stylish 1-bedroom condo at Icon Brickell, located in the heart of Brickell. This modern high-rise home features a comfortable bedroom, open living space, fully equipped kitchen, and in-unit washer/dryer. Walk to top restaurants, cafés, shopping, and nightlife. Building amenities include a pool, spa, and fitness center. Perfect for couples, business travelers, or a relaxing Miami stay.

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 Miami

5 out of 5 average rating, 3 reviews

Overlooking Miami Downtown,Room private & restroom

Disfruta de la sencillez de este alojamiento tranquilo y céntrico con una vista Panorámica Espectacular del Downtown de Miami, Zona Financiera Brickell y Miami Beach 🏖 , en el corazón de Little Havana cerca de la Famosa Calle 8 para comer y Bailar Salsa 💃🏻 y Ritmos Latinos .

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.

Apartment 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 Miami

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.

Superhost

Home in Miami

Spacious Family Home with Private Patio.

Spacious family home with cozy bedrooms, bright living spaces, and a multi-game table. Private backyard with fire pit, BBQ, hammock, and outdoor seating. Perfect for families and groups.