Holiday rentals in Big Pine Key

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.

Ocean Side Paradise Awaits!

This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic Ocean. Take advantage of the many tiki huts, fishing dock, air-conditioned clubhouse, and grilling station to cook up your fresh catch. Our turnkey townhouse is perfect for a short vacation or a longer-term stay. Everything in the complex, from the facilities to the furnishings, is brand new. Don't miss the opportunity to experience paradise at its finest. Book your stay now!

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

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.

Resort Condo: Pool | Marina | Beach | Pickleball

NEW LISTING! Experience the best of the Florida Keys in this prime location, offering both the luxurious amenities of a high-end resort and the cozy comforts of home, all with stunning views of the turquoise ocean. Enjoy access to an Olympic-size pool, hot tub, beautiful beach, marina, outdoor grills, tennis courts, pickleball, playground, and more. All of this comes at an excellent value, allowing you to spend more on the unforgettable experiences the Keys have to offer.

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.