Holiday rentals in Trumbo Point

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 New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Ocean Front Studio private Sandy Beach in Key West

Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to relax & enjoy waterfront living in this corner condo in historic Downtown Key West. Walk or bike everywhere—less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. On-site amenities include a heated pool, tiki bar & grills, parking, secure keyless entry, building elevator. Please note: The condominium dock will be under construction beginning April 27, 2026 for approximately 30 days; dock access will be unavailable and daytime construction noise is expected.

McCartney's Manor - Deluxe K Suite W/Pvt. Spa!

Beautifully decorated, step inside with cool pastel colors. The amenities include a blue tooth speaker, Alexa Echo, and a full kitchen with dishwasher. End your day by relaxing in front of the 65" Smart TV (bring your login information for Netflix/Amazon). The tumbled marble shower adds a luxurious touch to your stay. Located in a gated compound with 3 other units, you'll have privacy during your stay. The heated family pool is next door, while the adult heated pool is across the lane.

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

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.

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.

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Duval Corner - Pet friendly with Balcony

Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

Vacation home Island Suite 16

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.