Apartment holiday rentals in Florida Keys

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

5. Guest's Favorite: Waterfront Apt in Key Largo!

Embrace the tranquil waterfront lifestyle in Key Largo! Revel in picturesque boat views and indulge in freshly caught dishes served at nearby restaurants. Observe the serene presence of manatees, nurse sharks, and a variety of fish leisurely gliding through the canal. Conveniently dock your boat at the Pilot House Marina nearby. Our unit boasts a Modern, Spacious, and Impeccably Clean atmosphere, featuring Private Parking, Wifi, YouTubeTV, Refreshingly Cool AC, Plush Pillows, and a Cozy bed.

King Bed | Key West *Best Downtown Locations *Cool

AUGUST, SEPTEMBER, OCTOBER – We have significantly lowered our prices for the off-season. Please use part of the discount to purchase travel insurance at the time of booking. AirBnB Cancellations and Major Disruptive Events Policy excludes weather or natural conditions that are common enough to be foreseeable in a given location. Hurricanes are considered common and foreseeable in Florida between June and November, with peak activity typically occurring in August, September, and October.

Boot Key Harbor Retreat | Pool & Breakfast

Stay in a brand-new luxury 1BR/1BA Waterfront Suite on scenic Boot Key Harbor in the heart of the Florida Keys. Enjoy breathtaking marina views and resort-style amenities including a pool, Tiki Bar, waterfront restaurant, pickleball courts, fitness center, and complimentary breakfast. Ideally located between Islamorada and Key West, this elegant retreat is perfect for boating, beaches, fishing charters, waterfront dining, and unforgettable island adventures.

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs & DVD players.

OCEAN community, perfect condo

Experience coastal living in this modern 1BR/2BA condo in the gated Ocean Isles Fishing Village. Enjoy a king bed, new queen sleeper sofa, full kitchen, WiFi, A/C, and in-unit laundry. Relax in the oceanfront heated pool, fish from the pier, or launch your paddleboard onsite. OIFV offers 7 acres of oceanfront amenities, including a clubhouse, grills, and more. Perfect for a relaxing or adventure-filled stay in the Florida Keys!

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Top Floor - Oceanview condo with tennis courts, pickleball, hot tub, BBQ, marina & private beach. ★ "Exactly as described & very clean. Beautiful views & a nice peaceful escape." ➠ Resort size heated pool + Jacuzzi ➠ Balcony w/ ocean view ➠ Private beach access w/ sun lounger ➠ Fully equipped + stocked kitchen ➠ Double Master Suites ➠ 55” smart TVs w/ cable ➠ Car park (2 cars max) ➠ 250 Mbps WIFI

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

Historic 1880's Cigar Maker's cottage completely renovated. 1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV's, Full kitchen with granite counter tops, new stainless steel appliances. A newly remodeled bath with tumbled marbled tile, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!

Elevated Retreat | Sunset Access + Boat Basin

Elevated, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Set above the trees for a more open, airy feel, yet tucked into a peaceful setting. Enjoy walkable access to restaurants, shops, and breweries, plus fast WiFi and everything needed for a comfortable Keys getaway 🌴

Backwater Paradise

Clean, updated, and perfectly centered in middle of the island. Rental is a first floor 2 bedroom/2 bathroom unit with separate entrance. Living room opens up to the backyard with tranquil views of the water and docks. Take a complimentary backpack beach chair and take a short ride to the beach which is only a straight 1 mile ride down Winterberry Drive.

Duval Street Suites with full kitchen heated pool,

Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duval street in historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Waterfront Condo FREE Slip & Pool 2B2B in Key West

🌴 Key West Waterfront Paradise – FREE Dockage Included! Wake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes. Enjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.