Apartment holiday rentals in Monroe County

Stunning Studio w/Bay & City View Free Park/Pool

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

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!

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.

Luxury ICON Brickell Condo @47th Floor / POOL

This Unique and Deluxe 5-star Condo, Fully Equipped and located in the same building of the famous W Hotel, Icon Brickell, at 47th-floor with the biggest SWIMMING POOL in town. We are located on the mouth of Miami river on the sea, with amazing views of the sunrise in the morning and sunsets in the dusk. Steps from City Centre Mall, downtown, restaurants, cafés, and nightclubs. Five to six miles from Design District & South Beach. THIS IS THE PLACE TO STAY!

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.

#201 Key West Suites

Welcome to your charming, private studio apartment located right on Duval Street! Originally built in 1919, this historic building was once known as the Central Hotel due to its prime location at the heart of Duval Street, bordering Southard Street. While this is a vacation rental rather than a traditional hotel (no lobby, etc.), we've preserved the nostalgic feel by naming it "Key West Suites Hotel" in honor of its rich history.

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!

Early Bird Deal:Miami Studio w/Marriot Club Access

Welcome to your NEW studio at The Elser — a modern, resort-style tower in the heart of Downtown Miami. Stay steps from Kaseya Center, Bayside, Bayfront Park, and the waterfront. Enjoy the energy of the city outside and a calm, private space inside. ✨ 11+ years hosting · 10K+ 5-star reviews · 50K+ guests — we focus on clean spaces, smooth check-ins, and stays that simply work.

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.

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families

Duval Balcony Spanky's Retreat

Located in the heart of Duval Street, this one bedroom, one bathroom apartment with kitchen, and living area puts you right in the middle of all the action on Duval Street. Restaurants, bars, shops and attractions are just minutes away!