Condo vacation rentals in Monroe County

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Top-rated condo rentals in Monroe County

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Guest favorite

Condo in Tavernier

4.86 out of 5 average rating, 265 reviews

Condo in the Keys, Peaceful ocean view retreat!

Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Guest favorite

Condo in Tavernier

4.89 out of 5 average rating, 247 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 38 acres and one side is surrounded by a nature preserve.

Guest favorite

Condo in Tavernier

4.96 out of 5 average rating, 173 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Guest favorite

Condo in Tavernier

4.93 out of 5 average rating, 153 reviews

It's Tiki Time Ocean Pointe Penthouse 1 Br/1Ba

Stay at our tropical hideaway rated one the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort in the nature isle of Tavernier. You'll love the colorful mid-century modern decor that reflects the shades of this Keys paradise in the American Caribbean. With 60+ pristine acres, Ocean Pointe is the perfect blend of natural beauty and modern-day luxury and convenience for a great couples or small family getaway .

Guest favorite

Condo in Key Colony Beach

4.95 out of 5 average rating, 169 reviews

Keys Time Condo Oceanfront Complex Heated Pool

Impeccably clean - Beautiful new furnishings in private condo. Ocean front complex with heated pool in Key Colony Beach. Condo has king bed, new bathroom with walk-in shower and kitchen stocked with everything you need to cook complete meals (stove, oven, toaster, microwave, blender, fridge, etc). New smart TV with free Cable/Wifi and smart speaker for music. Relax on the private back balcony or beautiful private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Superhost

Condo in Key West

4.81 out of 5 average rating, 191 reviews

Large 2/2 Waterfront Condo Great View Pool & Dock

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Guest favorite

Condo in Tavernier

4.98 out of 5 average rating, 171 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 favorite

Condo in Key Largo

4.98 out of 5 average rating, 133 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACKETS/BALLS AND FISHING GEAR in a private beach resort community with a fishing jetty, a 24/7 boat ramp & a 3-acre salt-water lagoon for swimming, snorkeling, kayaking & paddleboarding. The condo sleeps 6 & is in the gated Kawama Community of Key Largo, surrounded by JOHN PENNEKAMP CORAL REEF STATE PARK. Marina boat slips may be available for rent.

Guest favorite

Condo in Marathon

4.9 out of 5 average rating, 111 reviews

10% Off November! Balcony, Pool Access & Marina

Welcome to THE MAD MAHI – your ultimate waterfront getaway! This stunning 1-bedroom condo (sleeps 4) in Marathon features a full kitchen, private balcony, resort pool, Tiki Bar, restaurant, and full-service Marina with boat ramp, trailer parking, and boat slips available. Enjoy exclusive access to the CABANA CLUB with its private beach, pool, and bar & grill. Perfectly located between Key Largo and Key West, with shops and dining just a walk or bike ride away.

Guest favorite

Condo in Key Colony Beach

4.92 out of 5 average rating, 130 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Superhost

Condo in Marathon

4.88 out of 5 average rating, 213 reviews

Sombrero Beach Tropical Getaway

Find an ideal home base for exploring the Florida Keys at our canal-front condo in Marathon, a cozy escape with a private balcony and easy access to the open ocean. You can spend your days boating, fishing, snorkeling, and lounging at Sombrero Beach, and return home each evening to a comfortable living space, a flatscreen cable TV, and an on-site Pool, tiki bar and restaurant! Vacation Rental Number - VACA-21-19

Guest favorite

Condo in Palmetto Bay

4.9 out of 5 average rating, 232 reviews

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.