Vacation rentals in Trumbo Point

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, 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.

A private hot jacuzzi is nestled under a sheltered area, surrounded by green foliage. Soft seating is positioned nearby, and natural light filters through the striped curtains. A staircase in the background leads to an upper level, while a wooden fence offers privacy.

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!

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.

Vacation home in Key West

A charming garden pathway is lined with lush tropical foliage, leading to a colorful green cart among vibrant plants. The surrounding trees provide a natural canopy, creating a serene atmosphere in this verdant outdoor space.

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.

4.97 out of 5 average rating, 259 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.

A serene private pool area is surrounded by lush tropical landscaping. Lounge chairs are arranged along the water's edge, inviting relaxation. A rock feature complements the pool, enhancing the natural ambiance created by palm trees and various greenery.

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!

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, 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).

A wooden pier extends into calm waters, leading towards a beach with soft golden sand. In the background, a multi-story building is nestled among palm trees, set against a sky with scattered clouds and a single bird in flight.

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 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).

4.87 out of 5 average rating, 246 reviews

A tranquil beachfront scene showcases a sandy shore lined with palm trees. Calm waters reflect the sky, dotted with fluffy clouds. In the distance, a marina displays boats alongside wooden docks, while cozy thatched-roof structures provide shaded seating.

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 vacation rentals in Trumbo Point

A private balcony area features comfortable seating with plush gray cushions and a glass-topped table. Lush greenery is visible in the background, and shutters frame the windows, allowing natural light to filter through while providing a sense of privacy.

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

A white wooden sign displays the words 'Garden House' surrounded by lush green foliage. Tropical plants and palm leaves frame the sign, creating a serene and inviting atmosphere in the outdoor setting.

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

A peaceful outdoor area features a blue swimming pool surrounded by lounge chairs. Lush greenery and tropical plants create a natural barrier, while a wooden lattice fence offers privacy. A sun umbrella provides shade for guests enjoying the poolside space.

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.

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 stately Victorian house is surrounded by lush greenery and tropical palm trees. The exterior features bright orange shutters and a welcoming front porch with decorative railings, providing an inviting entrance amid the vibrant foliage.

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

A balcony is presented with several beige chairs arranged around a small table. A potted orchid adds a splash of color. The space features wooden flooring and is bordered by white railings and dark shutters, providing a cozy outdoor seating area.

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!

An outdoor pool is surrounded by vibrant palm trees and colorful flowers. Stylish lounge chairs with bright cushions are positioned around the water. A covered seating area offers shade and relaxation, creating a welcoming space for guests to enjoy the sun.

4.67 out of 5 average rating, 113 reviews

Coastal Comfort | Sunset-watching. Outdoor Pool

JannetRating, 5 stars2 weeks ago

I can't understand all the negative reviews on Google Maps at all. The hotel was as advertised, it was clean and the staff were friendly. The only thing that bothered me was the volume from outside, because the balcony door doesn't really lock (not well sealed). But otherwise everything was perfect! The fees are transparent and you will be informed in advance. The shuttle was a good way to get into town.