Condo vacation rentals in Monroe County

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Top-rated condo rentals in Monroe County

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Guest favourite
A sandy beach area features tiki huts providing shade, with lounge chairs and umbrellas set along the shoreline. A pathway lined with palm trees leads toward the water, enhancing the tranquil beach atmosphere. The clear blue water glistens under the bright sky.
Condo in Key Colony Beach
4.98 out of 5 average rating, 327 reviews

Bright Cheery Condo, Ocean Views in Key Colony

Beautifully renovated condo in Key Colony Beach. with one king bed, well equipped kitchen with full-size appliances & everything you need to cook and serve meals. New A/C for great cooling. Renovated bathroom with walk-in shower, plenty of counter space and storage. Free & reliable WiFi with a private back balcony with chairs and table. Enjoy the heated pool & private sandy beach just steps away from your condo door. Sunset Park is next door, great for catching beautiful Florida Keys sunsets.

Guest favourite
Condo in Miami
4.94 out of 5 average rating, 255 reviews

Water View 48th Floor • 2B/2B • FREE Parking •Pool

Explore the luxury of this recently renovated high-rise condo completed in July 2026. It was beautifully designed with elevated finishes and stunning water views. Get free entry to all W hotel luxury amenities – Olympic pool, Jacuzzi, spa & gym. Also included is a free parking spot at a garage, just across the street, that normally costs $60/day! This suite is proudly hosted by SuCasa Vacay, offering the perfect blend of comfort, convenience and resort-style living. Property Name: SuCasa Vista

Guest favourite
A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.
Condo in Key Largo
4.9 out of 5 average rating, 163 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Kawama Yacht Club is situated between an extension of John Pennekamp Coral Reef State Park and a salt-water, filtered, tidal snorkeling lagoon! Two pools, tennis courts, private beach, a waterfront (lagoon) will keep you busy on site, while the neighborhood offers boating, many great restaurants and you may even swim with dolphins just outside the gates to the community. The townhouse comes equipped with two bicycles and two kayaks. All brand new appliances throughout + extra lg washer/dryer.

Guest favourite
A panoramic view captures the bustling downtown Miami skyline alongside the shimmering waters of Biscayne Bay. The image showcases a blend of modern high-rise buildings and green spaces, with bustling streets and the bay visible below, framed by a clear blue sky dotted with clouds.
Condo in Miami
4.93 out of 5 average rating, 116 reviews

39th Floor 3BR · Bay & City Views · Sleeps 8

Brand-new 39th-floor corner 3BR/3BA in downtown Miami's Worldcenter district, with panoramic bay and city views from a 250 sqft balcony and floor-to-ceiling windows. 1,300 sqft of space across three bedrooms — ideal for families and groups. Gym, resort-style pool, on-site dining (3 restaurants), and spa. Steps from Brightline, Metromover, Bayside, and Miami Worldcenter. Please note: A mandatory building resort fee of $35/night is required (set by the building, not the host). Paid parking only.

Guest favourite
A thatched-roof gazebo provides a sheltered seating area with wooden adirondack chairs. The serene ocean glimmers in the distance, while green navigation markers are visible on the water's surface. The structure features a wooden railing surrounding the space, enhancing the coastal atmosphere.
Condo in Tavernier
4.86 out of 5 average rating, 265 reviews

Toes in the Sand - 2 Bedroom Condo Sleeps 4

Two bedrooms and two full bathrooms on the 4th floor with ocean views. Amenities include a huge heated pool and hot tub with a bar, a beach cafe serving food and drinks, a private Key's beach, viewing pier, rentable boat slips & boat trailer storage, tennis, pickleball courts, basketball, children's swings, and BBQ areas, and gated entry with 24-hour security! Just remember that you're on "Island Time," mon, relax and enjoy! Perfectly located between Key Largo and Islamorada, close to Penneka

Top guest favourite
Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.
Condo in Key West
4.99 out of 5 average rating, 138 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Guest favourite
A modern kitchen features stainless steel appliances and white cabinetry, complemented by a light countertop. A dining area and living space are visible in the background, along with a staircase leading to the upper level. Large sliding doors provide access to an outdoor view.
Condo in Duck Key
4.88 out of 5 average rating, 112 reviews

Villa 5087 on Duck Key BOAT SLIP available

Enjoy a Fully Renovated Villa on Duck Key. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors, NO pets. Please do not take any items from the Villa. No pool access

Superhost
The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.
Condo in Marathon
4.93 out of 5 average rating, 117 reviews

Waterfront Condo, daily housekeeping & breakfast!

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

Guest favourite
A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.
Condo in Key West
4.9 out of 5 average rating, 297 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Guest favourite
A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.
Condo in Key West
4.88 out of 5 average rating, 274 reviews

Waterfront Dock Pool Condo Near Duval St Pet OK

Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.

Top guest favourite
A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.
Condo in Tavernier
4.99 out of 5 average rating, 223 reviews

Ocean Views at Ocean Pointe

Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 153 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

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