Holiday rentals with breakfast in Stock Island

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.

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. 🛥️🌴🎣

Beachfront Key West + Free Breakfast, Bar & Pool

Located at the quiet end of Duval Street, The Guesthouses at Southernmost Beach Resort offer an adult-focused sanctuary with a sophisticated Key West vibe. Guests enjoy "stay at one, play at all" access to the entire resort, including 3 pools, a private beach, and oceanfront bars. Walk to the Southernmost Point or relax in lush tropical gardens. Highlights include the beach-chic decor, world-class spa, and daily breakfast, blending boutique intimacy with full-scale luxury amenities.

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!

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.

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.

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 & will accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St, jet ski re

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.

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.*

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.

Oceans Edge Key West Resort & Marina

Ocean view balcony king features a king bed, private balcony with seating and ocean views, mini-fridge, smart TV, plush bathrobes, and custom amenities. Enjoy a spacious bathroom with walk-in shower, personalized Bluetooth entertainment, desk with multi-charging station, coffee maker, and high-speed wifi. Elegant, tropically inspired comfort for your island escape

Garden House TINY Queen Room

One-of-a-kind place accommodations in the heart of Old Town. These rooms feature one queen bed that can accommodate up to two people. Our Adults Only accommodations come complete with a quaint swimming pool and spa, in addition to, a free continental breakfast served daily.