Holiday rentals with a patio in Big Pine Key

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Beach House Getaway - Free Kayaks 2/2.5 Villa

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Keys Beach Retreat Close to Key West

Your family will be close to everything when you stay at this centrally-located place. we are only 3 miles from Bahia Honda Beach and about 27 Miles from Key West. We are perfect for nature lovers and adventure seekers. 1. National Key Deer Refuge: Home to the endangered Key deer, this refuge offers beautiful trails and great for wildlife viewing and 2.Looe Key Reef: A popular snorkeling and diving location, featuring vibrant coral reefs. 3.Sand bars nearby & world famous fishing spots.

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

3 Bedroom Home - Perfect Location & Private Pool

The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.