Holiday rentals with breakfast in Key West

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.

*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.

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.

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.

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.

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.

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.

Mo Room - 1 Queen, Shared bathroom, Breakfast

21 + age limit! Queen bed with funky art overlooking the front of the house on our 2nd floor. The bathrooms for this room are shared with 3 other rooms on our 2nd floor. 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. A favorite of repeat guests!

Duval St Apartment w/ Balcony w/parking Adult Only

This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*