Holiday houses in Trumbo Point

4.98 out of 5 average rating, 502 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 & BlueTooth stereo system with CD player & radio.

5 out of 5 average rating, 11 reviews

Heron Hideaway

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

4.93 out of 5 average rating, 111 reviews

WALK TO BEACH, MALLORY SQUARE, DUVAL STREET

Key West a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck. THE ADJACENT UNIT MAY BE AVAILABLE FOR ADDITIONAL SPACE.

4.87 out of 5 average rating, 322 reviews

Holiday home in Key West

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

4.97 out of 5 average rating, 260 reviews

Home in Key West

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

4.88 out of 5 average rating, 1,502 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

4.89 out of 5 average rating, 237 reviews

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.

4.9 out of 5 average rating, 207 reviews

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

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

4.97 out of 5 average rating, 100 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.9 out of 5 average rating, 186 reviews

Boat in Key West

Stay on the Roxie!

Enjoy, peaceful, ocean-breezy, star-filled nights, on the water! Free parking and free round trip transport 1 to & 1 from Roxie per night’s stay! Roxie is anchored in a protected, shallow 3-4ft lagoon. We live on a boat a half-mile away should you need anything. 😊 Roxie has a Keurig, snacks like chips, breakfast muffins or donuts , Keurig pods, bread, peanut butter and jelly, and bottled waters. No cooking but you may bring to go food, drinks. 🛥️🌴

4.96 out of 5 average rating, 280 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

4.87 out of 5 average rating, 246 reviews

Houseboat in Key West

Key West Luxury Houseboat at Yacht Club Resort

2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath PANORAMIC Ocean Views 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, HUGE SKY Deck Rooftop Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

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Other great holiday rentals in Trumbo Point

4.96 out of 5 average rating, 70 reviews

Speakeasy Inn-Room 2 (1 King Bed & Sleeper Sofa)

MarkRating, 5 stars1 week ago

This is a great spot along Duval Street that is quiet yet very accessible to all that the area has to offer. The downstairs rum bar is a definite bonus. Would definitely stay here again.

4.86 out of 5 average rating, 22 reviews

Private room in Key West

Garden House Queen Room

RussRating, 5 stars3 weeks ago

Amazing stay and even better than expected. The room was quaint and everything we needed. Close enough to walk everywhere. The amenities were great. I had forgotten there’s a little pool and that was a great treat after a long day in the sun. We’re already looking to book again!

4.9 out of 5 average rating, 153 reviews

Private room in Key West

Pink - 1 Queen bed, Shared bathroom

DagoRating, 5 stars5 days ago

I still gave a 5 although we had some issues checking in. The wrong key was provided at check-in; however they handled the hiccup quickly and timely. The location is close enough to all the action. The B&B is well stocked and they thought of everything to make your stay comfortable.

4.82 out of 5 average rating, 67 reviews

Blue Room at the Grand Maloney

DiegoRating, 5 stars2 weeks ago

Phenomenal place, the location was a big plus! you can walk everywhere. looking forward to staying again

4.98 out of 5 average rating, 43 reviews

Marrero's Guest Mansion Adult Only (21+) Room 12

LoriRating, 5 stars3 weeks ago

Great place to stay! Everyone was super friendly and very helpful. Location is great. Able to easily walk and explore the area and then come back and relax in a quiet setting. Loved the breakfast offered daily and all the amenities. Definitely would stay here again.

4.88 out of 5 average rating, 354 reviews

Private room in Key West

Mallory House Room #1

LindsayRating, 5 stars3 weeks ago

We had a great stay. It's on the quieter side of town with so many great restaurants. Easy to walk to other popular spots as well. David also helped check us in and found us free parking which we very much appreciated. Thank you for a wonderful stay!

4.67 out of 5 average rating, 113 reviews

Coastal Comfort | Sunset-watching. Outdoor Pool

JannetRating, 5 stars2 weeks ago

Ich kann die ganzen negativen Bewertungen bei Google Maps überhaupt nicht nachvollziehen. Das Hotel war wie angegeben, es war sauber und das Personal war freundlich. Das einzige was gestört hat, war die Lautstärke von draußen, weil die Balkontür nicht wirklich verschließbar ist (nicht gut abgedichtet). Aber ansonsten war alles perfekt! Die Gebühren sind nachvollziehbar und man wird im Vorfeld informiert. Der Shuttle war eine gute Möglichkeit in die Stadt zu kommen.