Vacation rentals in Big Pine Key

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Top-rated vacation rentals in Big Pine Key

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Guest favourite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 reviews

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.

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 113 reviews

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.

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 193 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Top guest favourite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 115 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Superhost

Boat in Marathon

4.8 out of 5 average rating, 286 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Superhost

Cottage in Little Torch Key

4.88 out of 5 average rating, 171 reviews

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!

Guest favourite

Home in Cudjoe Key

4.86 out of 5 average rating, 109 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Guest favourite

Villa in Marathon

4.91 out of 5 average rating, 360 reviews

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!

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 167 reviews

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.

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 114 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Guest favourite

Home in Cudjoe Key

4.93 out of 5 average rating, 185 reviews

106- Newly Renovated House with Oceanview and Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

Top guest favourite

Home in Marathon

5 out of 5 average rating, 117 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

See our home on HGTV's "Vacation House for Free", (Rental Lisc#VACA-20-690) BRING YOUR BOAT TO OUR PRIVATE 60 FOOT DOCK WITH 30 AMP SHORE POWER OUTLET. We call our home "Bahama Breeze" because that's what you feel blowing in as you spend your vacation at this Oceanside single family home.