Vacation rentals in Big Pine

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Perfect Couple Oasis!

You’ll treasure your time at this memorable location. New camper recently added to lot. Queen bedroom, bathroom, open living room with a full kitchen. Located on Big Pine Key, FL, between Marathon and Key West. Parking for 1 vehicle on lot, large vehicles will not fit. Key deer and roosters walk around park. Community pool and laundry facility. Great place to relax after fun in the sun or a night on the town! Renters must 25 years old or over. Community requires a rental form to be completed.

1 Bedroom Cabin Half/Duplex Unit B up on Stilts

You'll have a great time at this comfortable place to stay. 1 Bedroom Cabin located at the Old Wooden Bridge Resort and Marina in Big Pine Key, FL. 1/2 of a Duplex, up on stilts. It has a shared deck with a beautiful view over the marina. Guests can utilize amenities offered at Old Wooden Bridge Resort and Marina. There is NO Swimming in the Marina Boat Basin. This is a marina with houseboats and rental boats in the slips. There is a pet fee of $15 plus tax per night, per pet.

Lighthouse - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

The Island Gypsy

Reconnect with nature at this unforgettable escape. Property butts up to the endangered Key deer refuge with almost daily sightings in the yard. Only 6 miles offshore is Looe key and the 3rd largest reef in the world. Our lot has parking for 2 vehicles with a outdoor dining area and large backyard for hanging out. The island gypsy is our 5th wheel which sleeps 4 with a queen bed, queen bunk beds and a sofa bed. Heated pool in the park and right across street from clubhouse.

The Hideaway - Private Paradise at its Best!

Hideaway in your private paradise! This 3-bed, 2-bath home on a 1/4-acre lot offers serene surroundings and ocean views. Relax on the wrap-around porch for sunsets and stargazing. Boat ramp less than 5 minutes away with parking on property for your boat. Just minutes from beaches, the National Key Deer Refuge, and local attractions, it's perfect for both relaxation and adventure. Recent updates include new A/Cs, plus one in the 3rd bedroom. Your Florida Keys getaway awaits!

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!

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

106- Newly Renovated House with Oceanview and Pool

Sunrise Beach Resort gated community (11 homes, built 2007) 2 balconies, pool, dock, hammock, tropical landscaping Dock boats up to 25 ft; kayaks & paddleboards included 20 mins from Key West; near dining, Bahia Honda, Looe Key 2 master suites w/ king beds, en-suites & Smart TVs Open living/kitchen, BBQ, outdoor dining, parking for 3 Sleeps 6 w/ air mattress; Wi-Fi, streaming, towels provided No pets allowed

Cottage 30 min from Key West, free parking, pool

Get away from it all when you stay under the stars in this amazing little gateaway, surrounded by nature and amazing deers . This is Tiny house with 1 bedroom, 1 bathroom and 3 beds, accommodating up to 4 people!