Vacation rentals in Pigeon Key

NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!

NEW RENO! Welcome to The Keys Hideaway! 🌴🍍 The ✨ONLY✨ house in Marathon with its own private Pickleball Court and 4-Hole Putt-Putt Course!! Live your dream getaway in this Gorgeous 3BR Paradise in the heart of the Florida Keys. Sip a cold drink by your private pool🍹, play Pickleball🎾, enjoy Putt-Putt⛳, paddle out on a Kayak🌅, enjoy a bike ride🚲, or play Ping-Pong🏓, end the day with a family cookout🔥 At The Hideaway, you’ll have it all, adventure, relaxation, and unforgettable memories!✨

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

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.

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

Entire private two family water front home.

Forget your worries in this spacious and serene space. This is a great option for large multi-generational families that want to be in two separate areas of a full home. This is a full two family home with separate entrances. Enjoy 75 feet of waterfront with a concrete seawall, davits, a fish cleaning station, and direct ocean and bay access via nearby Vaca Cut. The home offers full privacy, a private heated and chilled pool in the heart of Key Colony Beach; the entire home is yours!

Beautiful Beachfront Home w/ Pool/Tiki/Dock

Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

Dapper Dolphin | Canal View + Breakfast + Pool

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

Private Gated Cottage | Hot Tub | Pet Friendly

License#VACA-23-370. Hot Tub, BBQ. Bring Your Boat, RV Parking. Conch Home located in the Heart of Marathon. Home sits on 8,000+sf lot w/2 bed (king in main BD & 2 twins in 2nd BD) 1 bath home w/ fully equipped kitchen & full bath w/shower & tub + lots of natural light & garden view all around. W/D, new mini split ACs in living room, & both bedrooms, back deck has a BBQ, Hot Tub & huge yard w/plenty of parking for a boat and trailer. YOUTUBE VIDEO TOUR: SEARCH sandys conch cottage

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

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!

Villa Mars In Marathon

Enjoy your Florida Keys Vacation at the NEWLY LISTED Villa Mars! This recently renovated two bedroom, two bathroom single level home is the perfect place for your tropical getaway! Centrally located on 29th Street in The City of Marathon, you will be right in the middle of all the action and attractions with most being within walking/biking distance. The home comes fully stocked with everything youll need to be comfortable during your stay!

70ft Dock, Bikes, Beach, Spacious, VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.