Vacation rentals in Pine Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Location · Family · Beach

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!

Value · Location · Grill

Cottage

Experience island living at Sugarloaf RV Resort & Cottages in the Lower Keys, just 25 minutes from Key West. Our NEW Two-Bedroom Cottages sleep up to 6 guests with two queen beds and a full-size pull-out sofa. Enjoy a kitchenette with a double-burner stovetop, pots, pans, dorm fridge, microwave, K-Cup coffee maker, toaster, dishes, and utensils. Relax on your private patio and enjoy resort amenities including a heated / chilled pool, kayaks, paddle boards, bicycles, and a peaceful private lake.

Location · Value · Parks

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.

Location · Value · Air conditioning

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.

Value · Location · Biking

Lagoona-Matata

A truly magical place "Lagoona-Matata" sits on the edge of Vaca Cut showcasing fabulous views of the Gulf. The outdoor area flows from the patio to the pool deck, private sandy beach, tidal pool and then to the pier dock. "Vaca Cut" is a fast-moving body of water from incoming to outgoing tides with fish of every kind moving through that makes fishing from the dock great entertainment. The continuous plethora of sea life in the lagoon makes this property an experience unlike any other.

Family · Location · Comfort

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.

Location · Value · Hospitality

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. 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 dock and enjoy the underwater scenery!

Location · Family · Check-in

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

Family · Location · Cleanliness

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!

Location · Value · Heating

Private Dock| 5min beach| Kayak| Sunset view|RV

Relax in this serene beach house, just a 5-minute walk from Sombrero Beach and a quick drive to Publix. Located in the heart of Marathon, FL, this home features its own boating dock, perfect for water adventures. The master bedroom includes a king bed, full bathroom, and closet. The second bedroom offers a king bed, bunk bed with pullout, and a nearby full bathroom. Enjoy a fully equipped kitchen, washer/dryer, kayaks (3) and trailer parking. Your perfect vacation getaway

Family · Value · Quiet

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.

Location · Value · Long stay