Holiday Homes in Florida Keys

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Value · Family · Condition

1. Key Largo Waterfront Studio | Canal & Ocean

Settle into calm at this bright, modern Key Largo waterfront studio at Waterfront Cabanas — a canal-front rental with direct ocean access to the Atlantic and Florida Bay. Watch boats drift past, manatees surface, and nurse sharks cruise the seawall, then unwind to the quiet rhythm of the water. Sleeps 4, with a full kitchen, walk-in shower, Smart TV, fast Wi-Fi, ice-cold A/C, parking, and a private boat dock (by reservation). Minutes from John Pennekamp Park, snorkeling, diving, and boating.

Location · Family · Cleanliness

The Mantell Plaza South Beach Studio balcony 01.

7 day minimum Charming Boutique building w/balcony, pool, gym & gardens. 1 block to Beach. Studio, cooktop, microwave. Washer, dryers in building. Minutes to Convention Center, shops, cafes, entertainment. Renovated. . TV FREE WIFI IN UNIT! Mantell Plaza. Sleeps 2 . SMOKING ON BALCONY ONLY. $600.00 USD CHARGE IF DETERMINED SMOKING IN UNIT. NO PARKING. Host Florida Realtor Cervera Real Estate, Inc. Elevator, stairs. Must have airbnb review. Provide photo identification after booking.

Family · Location · Air conditioning

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Family · Location · Comfort

Cabana Club Condo: Key Colony Beach, FL

Located on the Atlantic Ocean in the middle keys. Accommodations for up to 10 people. Waking up to the sounds of ocean waves and the beautiful waters of the Florida Keys is breath taking. Very few are on a private beach. The unit is very spacious and well kept. Large master closet for storage. Private entrance and Cabana Club access during operating hours: ( Monday 10-5, Tuesday-Sunday 10-7 ). New furnishings, full kitchen, clothes washer and dryer. Minimum one week rental, seven nights.

Family · Location · Backyard

Coral Gables Paradise 2

This property is centrally-located minutes away from South Beach, Miami Design District/Wynwood, Merrick Park , Miracle Miles and Coconut Grove. Perfect for families who want to walk in shopping malls, restaurants and the beautiful beaches Miami offers. For those who want to enjoy the nightlife, you will find Coconut Grove, South Beach, Wynwood, and Miami Design District between 10 and 20 minutes away. Here you will find the top-rated restaurants & most desirable lounges and clubs.

Location · Value · Check-in

4-bedroom house with pool steps from the dock!

Bring your boat and experience Big Cypress, the Everglades and 10,000 islands in luxury! We have parking for 6+ cars and a carport for your boat or kayak trailer. You can also have access to a dock with a lift upon request. All beds have extremely comfortable mattresses and smooth bamboo sheets that let you sleep like you are at home. Bring the whole family for tons of fun in the sun. Relax with open living space inside or lounge by the pool. Guaranteed not to disappoint!

Value · Family · Parks

Perfect Paradise

Relax with family and friends at this newly renovated Marathon getaway! Located minutes from Sombrero Beach, boat ramps, restaurants, shopping, and local attractions, it’s the perfect base for your Florida Keys adventure. Enjoy boat and trailer parking, complimentary kayaks, a fire pit, grill, patio dining area, and a fully stocked kitchen. After a day on the water, unwind in the king suite or relax under the stars. Perfect for families, anglers, and beach lovers.

Family · Value · Quiet

Location! 3 Apts •3 Parkings•Ocean Drive! Miami

Espanola Way Location! 2 blocks from the famous Ocean Drive! Miami Beach Highlights • 3 private apartments in one property • 3 FREE parking spaces • 2 blocks from the beach • Walk to Lincoln Road, Española Way & Ocean Drive • In the Historic Art Deco District • Ideal for family reunions, friend gatherings & business trips • Close to Miami Beach Convention Center Stay together, park for free, and experience the best of Miami Beach at your doorstep. 🌴☀️🏖️

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Location · Value · Heating

Beautiful Cozy Apartment.

Bring the whole family to this great place with lots of room for fun. Located in Homestead, you are in the central location for outlets, The Florida Keys, and Miami. 2 floor apartment with the main bedroom on the second floor. Also located on the second floor is the bathroom and shower. All Televisions are brand new smart Tv's. Avocado Villas is a quiet neighborhood, and the house is surrounded with security cameras for your protection.

Value · Family · Accuracy

Luxurious Apartment with views of Biscayne Bay!

New, fully equipped, apartment in Downtown Miami! The building is 3 years old with all the amenities a guest ask for! You Biscayne Bay and Miami beach from your room. Imagine being one block from Bayside Outdoor Mall , Kaseya center and walking distance to the Port of Miami! The pool is beautiful with a hot tub and cabanas to relax and enjoy to the downtown skyline. The gym is state of the art with peloton bikes! No pets allowed

Value · Family · Walkability