Apartment holiday rentals in Florida Keys

4.84 out of 5 average rating, 276 reviews

Apartment in Key Largo

5. Key Largo Waterfront Studio | Kayak & Reef

See why Cabana 5 is a guest favorite — a bright, modern Key Largo waterfront studio at Waterfront Cabanas, right on the canal with direct ocean access. Kayak the mangroves, snorkel the reef, and watch manatees and nurse sharks from your seawall, then relax as the sun sets over the water. Sleeps 4, with a full kitchen, walk-in shower, Smart TV, fast Wi-Fi, ice-cold A/C, parking, and a private boat dock (by reservation). Minutes from John Pennekamp Park and world-class snorkeling and diving.

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Superhost

A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.

4.84 out of 5 average rating, 146 reviews

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

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Superhost

A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.

Apartment in Tavernier

4.88 out of 5 average rating, 100 reviews

When Paradise is Key: Tropical Oceanfront Condo

🚨*PRICE YOU SEE IS ALL IN! Includes Airbnb fees and taxes!*🚨 🚨09.09.26 - 10.14.26 Elevator will be out of service due to installation of a new elevator 🚨 ☀️ Discover the ultimate beachfront getaway in our top floor, two-bedroom, two-bathroom condo, perfectly designed to offer an unforgettable escape. Nestled right on the oceanfront, this retreat comfortably accommodates up to six guests, making it ideal for families, friends, or couples seeking a serene coastal experience. ⛱️

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4.9 out of 5 average rating, 318 reviews

A bright studio space features a plush queen-sized bed and a cozy seating area with a Roku-enabled TV. The modern kitchen includes bar seating. Balconies overlook water views and a communal pool area, while tiki huts provide shaded outdoor lounging. Kayaks and paddle boards are readily available.

Apartment in Key Largo

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

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A spacious bed is framed by elegant side tables, each topped with a softly glowing lamp. Above the headboard, three framed artworks create a balanced focal point. Decorative pillows add a touch of color, while a leafy plant provides a natural element to the serene space.

4.95 out of 5 average rating, 480 reviews

Studio Blu -Hip Studio/Old Town

*Recent Update (2025): We’ve made a wonderful upgrade to the studio bathroom — it’s now fully enclosed with walls extending to the ceiling and a new exhaust fan for ventilation. Situated in the heart of the Cuban district, just steps from arguably the best café con leche in Key West, this bright and breezy studio apartment is minutes from everything on the island. No car needed — bikes and beach chairs are provided free of charge so you can explore at your own pace.

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4.98 out of 5 average rating, 561 reviews

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.

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4.92 out of 5 average rating, 279 reviews

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!

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4.93 out of 5 average rating, 245 reviews

Apartment in Tavernier

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

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The spacious studio features two large beds with light bedding. A contemporary sofa and chairs are arranged around a coffee table in the living area. The room includes a flat-screen TV mounted on the white wall, with ceiling fans and wooden flooring enhancing the bright atmosphere.

4.88 out of 5 average rating, 323 reviews

#203 Key West Suites

Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval Street bordering Southard Street and Duval Street! Although this a vacation rental and not a hotel per se with a lobby etc, we kept hotel in the name in keeping with historic nostalgia, "Key West Suites Hotel"

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4.92 out of 5 average rating, 968 reviews

A modern living area features a cozy couch covered with a soft blanket and a minimalist coffee table made of wood. A sleek television is mounted on the wall above a decorative sideboard. Natural light filters through sheer curtains, complemented by indoor plants.

Apartment in South Beach

Elegant 2-Bedroom 2-Bathroom on Ocean Drive

Coastal Breeze units bring in the freshness of the sea and the easy, seaside vibe of Miami. Each elegant beige-and-blue apartment offers a comfortable Queen-sized bed, an attractive and homey living area perfect for family or friends, a modern writing desk so you can mix in some business with pleasure, and all the space you’ll want for an airy, relaxing sanctuary in the ever-busy Ocean Drive.

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4.96 out of 5 average rating, 569 reviews

A multi-family property is shown, featuring a two-story structure with a balcony and large windows. Lush palm trees and tropical foliage surround the building, while a curved pathway leads to the entrance. The sky is clear with scattered clouds, contributing to a sunny atmosphere.

Apartment in Glades

Everglades City Getaway - 2 BR Apartment

Escape from the big city to the little City of Everglades! Centrally located to explore the Everglades and other parks in Southwest Florida. This Airbnb accommodates 4 people and is within walking distance of boat tours and local restaurants. The base price is for 2 people. Additional guests over 2 are charged $15/ per person per night.

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