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.

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!

It's 5 O'clock Somewhere 5 min drive to the beach

Escape to paradise in the heart of the Florida Keys! This stunning 4BR/3BA luxury home in Marathon offers the perfect blend of comfort, fun, & coastal charm. - Private heated/chilled pool - 36-ft dock with fish cleaning tables, water, and electric. Boat lift required. Fees apply. - Waterfront gazebo with 2-minute access to the ocean or gulf - Pet-friendly (fees apply) - Ping pong table and life-sized Connect Four - Sleeps up to 10 guests - 5 minutes to restaurants, attractions, & Beaches

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.

World-Class Oceanfront Pool/Hottub Sunset Escape

Escape to Oceans Cay Villas—luxury oceanfront in the Florida Keys. Why you’ll love the Islander: ✨ Heated swimming pool + Relaxing HOT TUB! ✨ Fire pit with perfect sunset views ✨ Fishing, snorkeling, and swimming in your backyard ✨ Free kayaks, paddle boards, and bicycles ✨ Walk or ride to Seven Mile Bridge ✨ Walking distance to restaurants and attractions ✨NO SEAGRASS SMELLS! ✨ Ping pong table ✨ Private dock for your boat ✨ Stylish, modern villa design ✨ Breathtaking SUNRISE and SUNSET views

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. 🛥️🌴🎣

Happy Manatee - 3 bed/2 bath 1/2 duplex home water

Happy Manatee - Waterfront Keys Coastal Retreat | 37’ Dockage | Tiki Hut | Cabana Club Private Access with private pool, beach and tiki bar. Key Colony Beach, FL Welcome to Happy Manatee, a laid-back island escape in Key Colony Beach. This 3BR/2BA waterfront home offers 37’ dockage, a private tiki hut, fish cleaning station, and bait freezer. Perfect for boating, fishing, and relaxing in true Florida Keys style. Pet friendly. Walking distance to Cabana Club. Easy Atlantic and Gulf access.

Waterfront Condo, daily housekeeping & breakfast!

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!

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.

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

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.

Bella's room - 1 Queen + 1 Twin, Shared bathroom

21 + age limit! This room is 2 beds - queen and twin for up to 3 adults. This room is the most spacious of the shared baths. The bathrooms for this room are shared with 3 other rooms. Both bathrooms are fully equipped with toilets, showers, sinks, body wash, shampoo, conditioner, hand towels, and hair dryers. Bath towels are in the rooms. We also have a plethora of outdoor sitting areas for guest use.