Holiday rentals with a kayak in Big Pine Key

Oceanside, Smart Home with SUP/kayaks - 60 FT Dock

This pet-friendly, waterfront home upgraded in 2021 (see notes) has two rooms with ample bedding - 1 king-size bed, one queen (pull-out sofa bed), and one full. The home has a cute kitchen that is well-equipped. A nice open area allows you to walk and enjoy the canal. Enjoy the ocean view or simply sunbathe in serenity. There is house parking in front for boats and trailers and covered parking for one car. It only takes minutes to access the ocean. We just completed construction of a 60FT dock.

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below March 30th - April 15th, 2025 April 23rd - May 3rd,  2025 May 17th - May 31st, 2025 June 6th - June 13th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

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.

Boaters delight! 1 min to open water, Dock & Beach

Inquire for monthly discounts. The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Dream Vacation KCB Marathon with private pool !

Dream Vacation Duplex in Key Colony Beach. Private pool Brand New state of the art house with all commodities and amenities, 3 bicycles 2 kayaks near to restaurants, fast WIFI, washer ,dryer, blue tooth speakers, night mood lights. A modern lift for boat up to 18000 lb Main canal Use of electric golf car Gem and jet sky and boat can be arrange Electric Gem-4 car offered for a minimum extra charge Options of private boat or jet sky (ask) Heated pool on demand (extra cost)

Living the Dream, Key West Style

Reconnect with nature at this unforgettable escape. Experience and enjoy what life is like living on a large 60 ft world cruising sailboat on the sailing vessel Serenity. Staying on Serenity is what Key West is known for and living a carefree lifestyle. Experience and enjoy the Artistic and Tropical landscaped private marina with spectacle views of the harbor. This is a all-inclusive price. No cleaning fee and includes 2 Paddle boards ,4 Kayaks and a large floating mat.

Waterfront&Dock/ kayaks,Hot tub/3mims to the beach

Waterfront Vacation Home just 1 minute from Publix & Winn-Dixie, and 3 minutes from Sombrero Beach! Beauty and The Sea beach house offers direct ocean access, 2 bedrooms, 2 bathrooms, a full kitchen, and spacious living room with queen sofa bed. Enjoy ocean views from your balcony, smart TVs in every room, high-speed internet, and local canals. Fully furnished with washer/dryer, kitchenware, towels, and more. Bring your boat or jetski—dock it right in your backyard!