Condo holiday rentals in Florida Keys

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

Family · Location · Getting around

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.

Value · Location · Condition

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.

Location · Value · Amenities

Waterfront Condo Dock Pool Downtown Near Duval

Time to relax and vacation in this spacious 1,350 sq ft waterfront corner condo in downtown Key West. Bring your family and friends and enjoy a private balcony with marina views, full kitchen, and open living space. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator access, and secure entry. Located about 1 mile from Duval Street and 10 minutes from EYW airport.

Family · Value · Laundry

Amazing Ocean Front Views Key Colony Beach

Everything is brand new in this gorgeous condo with amazing oceanfront views. #40 has two queen beds, well equipped kitchen with full-size appliances and everything you need to cook & serve meals. Fast, reliable WiFi, large SmartTV. Super cold new A/C unit Enjoy stunning views of sunrise from your private balcony & sunsets next door at Sunset Park. Heated pool, beach BBQs & tiki huts for guest use We are centrally located to awesome Keys adventures just a few miles drive from the condo.

Family · Value · Cleanliness

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.

Family · Location · Accuracy

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig & drip coffee New stainless appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, Beach, beach towels One parking space, no charge

Family · Value · Amenities

Dapper Dolphin | Canal View + Breakfast + Pool

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!

Location · Family · Cleanliness

Turtle Nest 1 Private beach,Pool, 2bed 2bath

Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.

Family · Location · Sleep quality

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.

Family · Value · Getting around

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.

Location · Value · Air conditioning

Ocean Shores Villa 2 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boatslip,kayaks,bikes,fire pit,hammock and heated pool). 32ft dock slip and trailer parking are included in the rental. Conveniently located near Sandbars, State Parks and many attractions.

Location · Family · Parking