Vacation rentals with breakfast in Key West

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Top-rated breakfast rentals in Key West

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The resort's outdoor pool area features a clear blue pool surrounded by lounge chairs. Palm trees are seen in the background, alongside a two-story building. Red umbrellas provide shade for guests enjoying the poolside atmosphere under a bright blue sky.

Apartment in Marathon

4.6 out of 5 average rating, 883 reviews

Standard 1 Bedroom King Suite with Balcony

Our Standard King One Bedroom Suite offers you with all the comforts of a home with a private balcony overlooking the hotel grounds. All Standard Suites have a private bedroom with a King-sized bed with memory foam mattress and a Sleeper Sofa in the living room area. Each suite is equipped with a full living and dining room area, with two 42’’ flat screen TV’s and a desk with USB charging stations. The fully equipped kitchenette provides you with dinner & silver ware, cups & glasses, a mini fridge, microwave and a coffee maker. The private bathroom has custom tiled showers and designer bath amenities by Hydra Spa.

A charming cottage is surrounded by lush tropical greenery, with a welcoming front porch featuring two oversized rocking chairs. The light pink exterior contrasts with the vibrant foliage, and the entrance is framed by tall palm leaves, creating a serene and inviting atmosphere.

Home in Key West

5 out of 5 average rating, 4 reviews

Poolside Cottage at Simonton Court - Adults Only

Your private cottage awaits you in paradise! Nestled among lush tropical gardens, this poolside cottage is part of our gated 2 acre adults only resort. Relax in any of our 4 pools – just steps from your door. Located 1 block away from infamous Duval St, yet still peaceful and secluded. A continental breakfast is included and is served poolside at the adjoining Mansion at Simonton Court. We also offer poolside beverage service, happy hour, food tours, bicycle rentals and concierge service.

A private dock extends into a serene canal, flanked by palm trees and landscaped with white gravel. Clear blue water reflects the sky, while nearby homes add a coastal ambiance to the scene. Sunlight creates a bright and inviting atmosphere along the waterfront.

Home in Marathon

4.83 out of 5 average rating, 6 reviews

*4 YR New* Private Dock/Cabana Club/Bikes & Kayak

Key Colony Beach Duplex, 2 Bedrooms (w/4 beds) 2 baths w/Cabana Club Access & Private 37.5 ft Dock on 100 ft wide Canal. This home has been recently remodeled, includes new furnishings, coastal décor, bedding, appliances and cookware. Master bedroom has an en-suite bathroom with a shower, flat screen TV, King bed, ceiling fan, and hairdryer. The second bedroom offers a bunk bed w/full size on the bottom and twin on top, flat screen TV is adjacent to a full bath with a hairdryer and a sofa bed.

An airy living space is showcased with a light-filled ambiance. Soft seating arrangements include a plush sofa and two patterned chairs. A dining area with metal chairs flows into a kitchen countertop, and sliding glass doors lead to a view of the outdoor area.

Home in Key Colony Beach

5 out of 5 average rating, 4 reviews

Key Colony Beach with Cabana Club Access

Key Colony Beach House with Cabana Club Access This 3 bedroom home with 37.5ft dock is an ideal getaway for fishermen, nature lovers, and sunbathers in search of warm weather, clear water, and tropical comfort. Walk into the open living room, where plush sofas create an inviting space that is full of light and the large windows frame the lush beauty outside. The full kitchen is equipped for cooks of all skill levels, and the dishwasher ensures that they won't waste one minute on chores.

A private pool is surrounded by tropical plants, illuminated by soft lighting that creates a serene atmosphere. The stepped entrance into the pool is clearly visible, and the tranquil water reflects the greenery above, enhancing the overall landscape.

Home in Key West

4.9 out of 5 average rating, 39 reviews

Millionaire Row Heart of Key West 4 BR Resort Home

5 Star Getaway With GREAT RATES - Renovated, WI-FI, Heated Pool and Garage. GREAT LOCATION!! Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for owners approval. Flexible cancellation policy. We try to beat rates of all the other houses in Truman Annex. Welcome to Island Living. Cozy, but upscale. Truman Annex is the most exclusive private residential community in Old Town Key West, just off the main drag of Duval Street.

Top guest favorite

A serene outdoor space features a clear swimming pool surrounded by palm trees. A covered lounge area provides shade, while lounge chairs offer spots for relaxation. The tranquil waters are visible in the background, enhancing the overall atmosphere of the private retreat.

Home in Marathon

5 out of 5 average rating, 14 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Looking for the perfect home for your next Florida Keys vacation? Waterfront home with over 100 feet of dock space. Just a short boat ride out to Sombrero Beach and open water for a day of fishing, snorkeling or cruising around. Our Coastal home has a secluded setting, nestled at the end of the road, with water views & Sunsets that never disappoint!! Additionally, you will enjoy your own private beach and heated pool... complete with Hammock, Adirondack chairs and lots of outside seating.

Top guest favorite

A bright cabana room features a spacious bed adorned with colorful pillows. Large glass doors open to a view of the pool area, allowing natural light to brighten the space. Vibrant floral wallpaper complements the light tones of the decor, contributing to a tropical ambiance.

Hotel room in Key West

4.98 out of 5 average rating, 50 reviews

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

Adult Only Boutique Hotel (21+). Experience the grandeur of their stately Victorian home, thoughtfully updated and lovingly converted into a boutique hotel. We are located in the heart of Old Town, just half a block from Duval Street. This beautiful room is right next to our revitalizing saltwater-treated pool. Separate from the main house, this cabana room offers guests a more private tropical escape. This room features a pillow top king bed with a private bath and sitting area.

Guest favorite

The vacation home features a spacious under-house parking area surrounded by lush palm trees. The two-story structure has a wrap-around balcony adorned with wooden railings. Clear blue skies provide a bright backdrop, enhancing the home's inviting presence.

Home in Marathon

4.9 out of 5 average rating, 20 reviews

Villa Casa Cayo

Beautiful Marathon vacation home in the Sombrero Beach area, this waterfront vacation rental is surrounded by lush tropical gardens and a newly constructed pool. Only 300 meters from beautiful Sombrero Beach. Open concept home with wrap around balconies and views of the water. Hurricane impact doors and windows and new metal roof just completed in 2022. It's a 5 star! Tie your boat or kayak up for easy access to the Atlantic Ocean. Family friendly, just 45 minutes from Key West.

Top guest favorite

A bright room features a spacious bed adorned with tropical-themed pillows. Natural light filters through a large window with blinds, and a door leads to an outdoor area. A plush bench and a small wooden table add to the inviting decor.

Private room in Key West

4.98 out of 5 average rating, 136 reviews

Steps off Duval - Paris - Beautiful Queen Room, Included in the price: breakfast, happy hour, bicycles.

One of 6 rooms at Andrews Inn! Neighbor with the Hemingway House, a beautifully decorated room with private bathroom, air conditioning, ceiling and tower fan, a new queen-size NECTAR mattress, Smart TV with Netflix, free Wi-Fi, in-room refrigerator. Guests staying here must be able to climb a single flight of stairs. We are an owner-operated Guest House where you will feel a lovely welcoming and a relaxing atmosphere. Included in the price: breakfast, happy hour, bicycles.

Superhost

The exterior of the modern home showcases a spacious backyard featuring a heated swimming pool, fire pit, and lounge chairs. Lush green grass surrounds the paved pathway leading to the entrance, with the house's contemporary design highlighted against a colorful sunset backdrop.

Villa in Marathon

New place to stay

Ocean Muse - Lux Waterfront Escape - Pool - Dock

Step into Ocean Muse, a luxurious 4BR 3Bath waterfront escape in peaceful Marathon, FL! Enjoy a private backyard with heated pool & spa, fire pit, dock, elevator, and stunning ocean views at Ocean Muse—just minutes from top attractions. ✔ 4 BRs (2 Master Suites, Bunk Room) ✔ Open‑Design Living ✔ Full Kitchen + Wet Bar ✔ Backyard w/ Lounge, Pool, Fire Pit, Games, BBQ ✔ 40' Dock w/ Fish Station ✔ Rooftop Ocean Views ✔ Elevator to All Levels ✔ Minutes from Top Attractions

Guest favorite

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

4.91 out of 5 average rating, 199 reviews

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. 🛥️🌴

Guest favorite

A two-story yellow villa is seen against a clear blue sky, featuring a private pool surrounded by lounge chairs. The outdoor area includes a grassy lawn and is bordered by a white fence, enhancing the space for relaxation and enjoyment.

Home in Marathon

4.98 out of 5 average rating, 66 reviews

Luxury 4/3 Waterfront/Private Heated Pool/Dock/Ice

Located on Sombrero Beach Road, Paradise Cove is a new and luxurious 4 bedroom and 3-bathroom Villa with plenty of space to comfortably accommodate up to 10 guests. The spacious Villa offers three Master King Suites, one on the first floor and two on the second floor. You will find a fourth Bedroom with full bunkbeds on the second floor as well! Daily rate includes unlimited use of Pool Heater, Ice Machine, and multiple amenities during your stay.