
Condo holiday rentals in Monroe County
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Top-rated condo rentals in Monroe County
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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.
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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.
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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
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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.
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Cuban Paradise @ Cuban Club
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy two-bedroom condo has a private balcony to enjoy all the hustle and
Hospitality

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!
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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.
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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.
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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.
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Tropical Heron Hideaway w/ Hot Tub + Pool
Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.
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Bright Modern Studio Apartment
Find yourself at this slick Studio Apartment professionally designed, top of the art appliances with a unique modern touch. Based in a quiet and peaceful neighborhood. Located close to Downtown Miami and also to The Florida Keys. Nearby shoppings centers, restaurants and supermarkets. All you need to enjoy a charming getaway.
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Tequila Sunrise
Licensed FL Vacation Rental CND5404099 Enjoy a stylish experience at this newly renovated 2 bedroom condo looking right into the ocean. Located in Building 3 directly across from the pool and a 2 minute walk to the beach and marina. Enjoy amazing ocean views from the balcony!
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Popular amenities for Monroe County condo rentals
Weekly condo rentals

Oceanfront Sunrise Condo Private Beach Heated Pool
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Reel Large END Unit in Ocean Point Suites
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Tropical Escape at Sunrise
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Oceanfront Brickell Miami Condo 20 Pool Free Parkg
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Affordable Beachfront Luxury Condo Sleeps 6
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SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
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Ocean Shores Villa 2 with pool and boat slip
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Slip, Private Ramp, Pool, Trailer Parking, Freezer
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Pet-friendly condo rentals

Luxury Loft: 270° views, Rooftop Pool, Parking
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Icon Brickell (W) Huge unit with bay & river views
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Luxe Penthouse in Downtown Miami
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Walkable Apt with Free Garage Parking
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Modern Self Check in, Parking, Wi-Fi, Pets Ok
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🎖W Hotel Residence 2 bedrooms
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Sunrises - Sunsets - Free Kayaks
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Beautiful BAY VIEW Apt, 2/2br 1100sqf
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Condo rentals with a pool

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
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Spacious 2BR Queen Suite | 2 Bath | Sleeps 6
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Grand Marina Suite - Poolside & Waterfront Condo
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Anchor Drop modern elegance upgrades throughout vi
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Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
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EYW Getaway
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Condo in Tavernier
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Fully renovated 2/2 bath condo w/ shared pool!
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Coral Castle
- Bahia Honda State Park
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- Everglades Alligator Farm
- Theater of the Sea
- Ernest F. Coe Visitor Center
- Key Largo Kampground And Marina
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Monkey Jungle
- Harry Harris Beach and Park
- Founder's Park
- Calusa Campground
- Homestead Bayfront Park
- Everglades Safari Park
- Conch Key
- Fruit & Spice Park
- Zoo Miami
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