Vacation rentals in Trumbo Point

The view from a balcony showcases lush tropical foliage, featuring an abundance of green palm leaves that create a serene and inviting backdrop. Sunlight filters through the leaves, adding a soft glow to the vibrant greenery.

4.77 out of 5 average rating, 362 reviews

Key West - Sunrise ❀ The Green House

Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable price and enjoy! ♡ Best location for exploring Key West, in the epicenter of Old-Town and all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride. Check out the map and see all attractions right around The Green House!

A calm waterfront scene is captured at sunset, showcasing a dock structure with a roof extending over the water. Soft hues of pink and purple reflect in the water, with palm trees and lush greenery framing the view, creating a serene ambiance.

4.98 out of 5 average rating, 505 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.

A covered deck features two lounge chairs with blue cushions, accompanied by a small round table. Lush green palm trees and tropical plants surround the area, while soft natural light filters in, creating a serene outdoor space for relaxation.

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.

A charming exterior features a bicycle adorned with vibrant flowers, positioned above a welcoming entrance. Lush greenery surrounds the quaint home, enhancing the tranquil atmosphere. The light blue siding and striped awning add to the inviting character of the property.

4.95 out of 5 average rating, 319 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!

Vacation home in Key West

4.87 out of 5 average rating, 322 reviews

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.

An aerial view showcases a vibrant pool surrounded by lush palm trees, creating a serene tropical oasis. The pool's turquoise water reflects the greenery, while lounging chairs are placed nearby for relaxation.

4.84 out of 5 average rating, 1,338 reviews

At Mine | Key West 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!

An inviting pathway is flanked by charming wooden structures, featuring pale green shutters. Lush greenery and tropical plants complement the brick walkway, leading toward the lush landscape beyond. The setting conveys a sense of tranquility and a connection to the vibrant surroundings.

4.89 out of 5 average rating, 238 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.

4.97 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

A waterfront seating area is portrayed, featuring round tables surrounded by teal chairs. Umbrellas provide shade as guests enjoy the scenic view of the sunset over the water. The outdoor space is paved with light-colored bricks, enhancing the open and inviting atmosphere.

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. 🛥️🌴

A modern kitchen area features gray cabinetry and white countertops, with stainless steel appliances visible. To the left, a seating area with a large turquoise couch and dining table overlooks the waterfront through floor-to-ceiling windows.

4.87 out of 5 average rating, 201 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

The kitchen features modern white cabinetry with ample storage space. A stainless steel refrigerator and microwave are positioned alongside a smooth top stove and dishwasher. Light-colored countertops enhance the open and clean design, while a sink is conveniently placed beneath a window.

4.9 out of 5 average rating, 275 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"

A charming entrance is revealed by a white picket fence, leading to a lush, landscaped pathway bordered by tropical greenery. A spacious patio area with dining furniture is visible under a large awning, while the upper balcony invites relaxation among the palm trees.

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).

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Other great vacation rentals in Trumbo Point

4.95 out of 5 average rating, 20 reviews

Two wooden chairs provide seating on the deck of the houseboat, facing the open waters of Key West. Large glass doors lead into the kitchenette area, with a view of the serene sea and sky, emphasizing the peaceful outdoor setting.

Houseboat in Key West

Shanty Pineapple Key West

BlakeRating, 5 stars3 days ago

Tony was an excellent host! We are locals and did this as a staycation. Beautiful views, and really comfortable space. Highly recommend this spot! The kayak was an awesome addition, there’s a little sandbar and island close by. Would definitely do this again.

A modern countertop is highlighted by a bronze faucet, complemented by clear glass jars filled with yellow bath sponges. The backsplash features a subtle blue herringbone pattern, adding a refreshing touch to the serene bathroom environment.

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

A spacious shared balcony is highlighted by a light blue ceiling and white railings. Several white chairs are arranged along the length, offering views of lush palm trees and rooftops of nearby structures. Natural light illuminates the area, enhancing the relaxing atmosphere.

5 out of 5 average rating, 7 reviews

Duval Corner - Pet friendly with Balcony

JulianRating, 5 stars3 weeks ago

Beautiful little apartment right on Duval Street. Really was a small slice of paradise.

4.96 out of 5 average rating, 82 reviews

A spacious bathroom features a large mirror above a modern sink with organized storage underneath. A shower area is visible to the left, with towels arranged neatly on a shelf. The soft color palette adds to the room's bright and airy feel.

Hotel room in Key West

Speakeasy Inn - Room 3B (2 Queen Beds)

MeghanRating, 5 stars1 week ago

The Speakeasy Inn was just what we were looking for to enjoy Key West! It was within walking distance to so many restaurants and coffee shops. The butterfly garden was just a block away. And was far enough away from the main strip/louder part of Duval street at night but close enough to walk to bars and the late night fun. Very clean and Raymond and Lindsey were super friendly and responsive. Highly recommend staying here!

4.98 out of 5 average rating, 102 reviews

A well-lit bathroom features a white sink with a polished faucet and a large mirror above it. The walls are paneled with light-colored wood, complemented by a window with delicate white curtains. Soft white towels are neatly hung on a rack nearby, adding to the room's cleanliness.

Private room in Key West

Bates - 2 full beds, private bathroom

SaraRating, 5 stars1 day ago

Our stay was relaxing with crisp air always circulating in our room and yummy breakfast each morning! We appreciated the pool and the ease and ability to rent bikes during our stay!

4.73 out of 5 average rating, 49 reviews

A plate is presented with a classic burger topped with melted cheese, lettuce, tomatoes, and pickles. Golden, crispy French fries accompany the burger, resting on parchment paper within a circular dish. The background features a tranquil pool area with lounge chairs and umbrellas.

Hotel room in Key West

Luxurious Stay | Snorkeling. Outdoor Pool

LaurenRating, 5 stars2 weeks ago

The maker is beautiful for a honeymoon stay in the Florida keys!

Hotel room in Key West

4.76 out of 5 average rating, 338 reviews

Newly renovated + Free Full Breakfast - King Bed

AmberRating, 5 stars2 weeks ago

This was a lovely stay. Well designed and taken care of. It had anything and everything you would need. I hardly wanted to leave to explore the island.