Holiday rentals in Trumbo Point

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Top-rated holiday rentals in Trumbo Point

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Guest favourite

Apartment in Key West

Boat Slip - Waterfront Condo - Key West Pool

Be among the first to experience this spacious waterfront Key West getaway, newly available as a vacation rental! Enjoy a heated pool, marina views, an oversized private balcony, and over 1,200 sq ft of living space, all just minutes from Duval Street. Complete with a full kitchen, free parking, elevator access, pet-friendly accommodations, high-speed WiFi, and a private boat slip. Perfect for boating, fishing, beaches, and everything Key West has to offer. Pet friendly. 10-min from EYW airport.

LocationFamilyComfort

5.0 out of 5 average rating, 11 reviews

Guest favourite

Home in Key West

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!

ValueLocationWalkability

4.82 out of 5 average rating, 17 reviews

Top guest favourite

Hotel room in Key West

The Sanchez House Room #2

There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.

ValueLocationCheck-in

4.85 out of 5 average rating, 711 reviews

Guest favourite

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

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. 🛥️🌴🎣

FamilyValueDecor

4.89 out of 5 average rating, 247 reviews

Guest favourite

A private conch cottage floats on calm waters, featuring a light green exterior with white trim. Spacious decks are present at the front and back, while paddle boards and kayaks are visible nearby, highlighting the connection to the surrounding nature.

Houseboat in Key West

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

LocationFamilyAccuracy

4.95 out of 5 average rating, 84 reviews

A spacious houseboat floats gracefully on calm waters under a vibrant blue sky. The exterior features a sleek white design with large windows, providing ample natural light. A small dock extends from the side, offering convenient access to the boat.

Houseboat in Key West

Happys Houseboat

Looking for a unique and unforgettable vacation experience in Key West? Look no further than this charming houseboat listed on Airbnb! Escape the ordinary and indulge in the tranquility of living on the water. Our houseboat offers all the comforts of a cozy home, with the added bonus of breathtaking views and a prime location. Included in the rental is use of a skiff to get to and from land and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

FamilyValueGetting around

4.79 out of 5 average rating, 280 reviews

Guest favourite

A comfortable room features a spacious bed with crisp white linens, positioned against a coral-themed accent wall. Natural light streams through a window with white shutters. A small dining table and chairs complement a kitchenette area, while a large mirror enhances the sense of space.

Flat in Key West

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!

ValueLocationSolo travel

4.86 out of 5 average rating, 1744 reviews

Guest favourite

Home in Key West

Old Town Key West Escape - The “Eyebrow Saltbox”

28 Night Minimum. Welcome to "The Saltbox"! 710 Ashe Street is a charming house circa 1889. This historic Eyebrow home offers classic elegance and history with modern comforts. A spacious living area, sleek kitchen, three tropically decorated bedrooms (1 King and 2 Queen Beds). 6 person max. Private and heated Cowboy pool. Conveniently located in Old Town, walking distance to shops and attractions and Duval St. Local Key West Artist Designed.

LocationValueBeach

4.88 out of 5 average rating, 16 reviews

Guest favourite

A floating home is anchored in calm waters, featuring a sleek design with large windows. Two red buoys are visible alongside the vessel. A paddle board rests on the top deck, which is covered for shade, inviting guests to relax while taking in the surrounding nature.

Boat in Key West

“The Easy Way” Comfy, Practical, Convenient

Reconnect with nature at this unforgettable escape. Stay off Key West away from the crowds and listen to nature. Vessel “Easy Way” is perfect for up to 2 people. Come enjoy the amazing sunrise and sunset. Cook out on the balcony, watch fish, birds, stingrays, and dolphins go by. Vessel Easy Way has an outdoor shower, paddle board, and outdoor grill. This floating home is perfect for people who want to relax and enjoy nature.

LocationCleanlinessIndoor spaces

5.0 out of 5 average rating, 24 reviews

A view of the resort pool area is framed by lush palm trees and greenery. Loungers are positioned around the pool, inviting relaxation. The scene is brightened by clear blue skies, creating an atmosphere of leisure and tranquility.

Apartment in Key West

Poolside Suite with Direct Pool Access

Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

ValueFamilyDecor

4.78 out of 5 average rating, 115 reviews

Guest favourite

The Tiki Suite is presented on a wooden platform, showcasing thatched roofing and an inviting porch area. Two stand-up paddleboards are placed alongside the structure, with calm waters reflecting the clear sky.

Houseboat in Key West

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

ValueLocationNearby

4.91 out of 5 average rating, 562 reviews

Superhost

The balcony offers stunning views of the turquoise waters and sandy beach, framed by palm trees. A resort-style pool can be seen nearby, and the expansive outdoor space invites relaxation under the sun, enhancing the beachside atmosphere.

Apartment in Key West

Windswept Palms at The Beach

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. WINDSWEPT PALMS has been thoughtfully decorated and furnished.

FamilyLocationAmenities

4.95 out of 5 average rating, 43 reviews