Holiday rentals with breakfast in Key West

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.

Family · Value · Check-in

Gorgeous 3 Bdrm Home w/ private pool, 60' dockage

🌴 4 Ever Big Sky – Coastal Luxury Retreat | Private Pool + 60’ Dockage | Key Colony Beach, FL | 3 Bedroom plus bonus Florida Room/ 3 Bath Welcome to 4 Ever Big Sky, a sophisticated waterfront escape where modern coastal design meets effortless Florida Keys living. Ideally located on prestigious 12th Street in Key Colony Beach, this beautifully curated home features a private pool, 60 feet of dockage, and an unforgettable outdoor oasis designed for both relaxation and entertaining. ✨ The Expe

Family · Location · Cleanliness

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

Oasis in The Keys, as the name implies, is a haven for guests looking to escape the everyday and enjoy the relaxing peace and beauty of The Florida Keys. Sit back and relax in this spacious and luxurious amenity filled waterfront home with floor to ceiling views of the turquoise blue Caribbean waters. This home has everything you need to enjoy your vacation without having to go far, though should you venture out it's central location makes it ideal for anyone looking to explore the middle keys!

Value · Family · Getting around

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.

Family · Location · Comfort

Marrero's Guest Mansion Adult Only (21+) Room 7

Adult Only (21+) Boutique Hotel. Experience the grandeur of the stately Victorian home, thoughtfully updated and lovingly converted into a boutique hotel. Located in the heart of Old Town, just half a block from Duval Street. This second floor room has a long and distinctly resonant history thanks to the benevolent touch of Enriquetta Marrero, the former wife of the mansion's original owner. Mrs. Marrero's favorite room includes a pillow top king bed, private bath, sitting area, and balcony.

Value · Location · Amenities

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. 🛥️🌴🎣

Location · Value · Outdoor spaces

Dapper Dolphin | Canal View + Breakfast + Pool

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

Value · Location · Getting around

Key West Orchid Garden Duplex @ Suite Dreams Inn

Suite Dreams Inn is an intimate family-owned boutique Key West Bed & Breakfast in the tranquil upscale Casa Marina Old Town neighborhood, offering oversized suites with luxurious king & queen beds, kitchens, living rooms, 2 pools, 24/7 laundry, free parking, and relaxing outdoor spaces. We are LGTB & pet friendly & well accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St, jet ski re

Location · Family · Biking

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.

Value · Location · Breakfast

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

Family · Location · Hospitality

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.

Value · Location · Outdoor spaces

The Artist House Key West - Upgraded King Suite

Upgraded king suite. Once the master bedroom, this spacious suite at our romantic Key West, FL inn features an elegant king bed, Dade County pine floors, sofa, TV and an opulent bathroom featuring a clawfoot slipper soaking tub, large glass shower and an abundance of space. This Upgraded King Suite is located on the second floor. This romantic escape was recently remodeled and is one of our most popular rooms.

Location · Decor · Walkability