Vacation rentals in Pine Key

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Top-rated vacation rentals in Pine Key

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Guest favorite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 129 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.

Superhost

Tiny home in Big Pine Key

4.81 out of 5 average rating, 196 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Top guest favorite

A spacious outdoor Tiki Hut provides shaded seating with wicker furniture around a table. Sunning loungers are arranged nearby, facing the water. A ceiling fan circulates air above, while scenic views of the waterway and dock are visible in the background.

Home in Key Colony Beach

4.96 out of 5 average rating, 105 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 favorite

A modern washing machine is showcased beside a stainless steel countertop. A glass container labeled 'Homemade Laundry Soap' is placed nearby. Natural light filters through sheer curtains, enhancing the functional space.

Tiny home in Big Pine Key

4.93 out of 5 average rating, 76 reviews

Tiny Fish Haus

Come experience Tiny Home Living in this Park Model RV right next to the National Key Deer Refuge! . Relax on our covered patio next to a large Saltwater Swimming Pool, Cook dinner on a Blackstone grill , enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..explore Big Pine Key with our 2 bicycles that are included .AirPurifier for clean air inside. 28 Miles to Key West. Keys Shuttle located next to our park

Top guest favorite

A thatched-roof building is seen surrounded by lush palm trees and colorful tropical plants. A clear sky is visible above, and a vehicle is parked in the driveway, indicating convenient access to this vibrant establishment.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 109 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!

Guest favorite

An aerial view showcases the property situated by the ocean, with a private beach area lined with palm trees. The bright blue roofs of the buildings contrast with the lush greenery and the sparkling turquoise water, highlighting the inviting outdoor pool and surrounding lounge areas.

Condo in Key Colony Beach

4.96 out of 5 average rating, 208 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Superhost

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

4.8 out of 5 average rating, 271 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.

Guest favorite

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 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 favorite

Home in Key Colony Beach

4.95 out of 5 average rating, 116 reviews

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.

Guest favorite

Three colorful Adirondack chairs, yellow, turquoise, and green, are positioned on a sandy beach facing a calm blue ocean. A rocky shore and sparse greenery surround the seating area, while fluffy white clouds drift in a bright sky, enhancing the serene water view.

Villa in Marathon

4.91 out of 5 average rating, 322 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 favorite

The houseboat is illuminated with green lighting at night, creating a striking reflection in the water. The exterior features a porch with white railings, while the name 'Hokey Couch' is displayed above the entrance. The surrounding area is calm and dark, enhancing the serene ambiance.

Houseboat in Marathon

4.89 out of 5 average rating, 120 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Guest favorite

A black and white Jeep is parked in the gravel driveway of a charming yellow house. The house features large windows and is surrounded by palm trees, under a partly cloudy blue sky. A blue recycling bin is visible in the foreground.

Home in Marathon

4.9 out of 5 average rating, 162 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

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Popular amenities for Pine Key vacation rentals

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Other great vacation rentals in Pine Key

A bright living space features large windows with light-filtering shutters, offering a view of the outside. A spacious day bed is positioned near the windows, complemented by a rustic dining table and chairs. The adjacent kitchen includes modern appliances, enhancing the open layout.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars3 weeks ago

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

A modern RV is parked in front of a vibrant blue home, showcasing a well-maintained yard with palm trees and gravel. The house features large windows and a contemporary design, offering a sense of spaciousness and outdoor living. The setting highlights a relaxed, coastal atmosphere.

Vacation home in Big Pine Key

5 out of 5 average rating, 5 reviews

Boater dream home 75ft wide crystal clear canal

KathyRating, 5 stars14 months ago

My husband and I, along with some friends, stayed the month of March. The description of the house is accurate; clean, homey, comfortable beds, nice furnishings and decorated nicely. A few minor issues came up while we were there and Kelly & Walter responded very quickly to resolve! We kayaked/paddle board with manatees in the canal right outside our front door, to include different kinds of fish. I enjoyed my morning runs on the bike/walking trail at the end of our street. Also, met many nice neighbors as well while walking our dog. The weather was beautiful, only rained 3 days the entire time we were there. The boat lift and pool were a plus, after a day of boating we would come back and cool off in the pool. We enjoyed our stay so much, we have already booked March of next year!!! Thank you Kelly & Walter for sharing your home with us!

A sandy waterfront area is lined with colorful lounge chairs. The inviting blue waters stretch into the distance, while palm trees provide shade. Wooden pilings are visible in the water, contributing to the serene coastal environment.

Houseboat in Marathon

4.82 out of 5 average rating, 11 reviews

Tiny Home Aqua Lodges 2/1

JasonRating, 5 stars2 weeks ago

Great spot. Would stay again

Guest favorite

Home in Marathon

4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars3 weeks ago

Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

Superhost

Aerial view of the Venture Out community showcases a large swimming pool adjacent to the sandy beach. Palm trees surround the area, with calm turquoise waters extending into the distance. Amenities include a tiki structure and a spacious lounging area, ideal for relaxation and outdoor activities.

Home in Cudjoe Key

4.88 out of 5 average rating, 32 reviews

Waterfront FL Keys Cottage @ Venture Out

ElizabethRating, 5 stars4 days ago

Great location, easy access to everything, lots of amenities on the community.

Superhost

A well-equipped kitchen features stainless steel appliances, including a refrigerator and dishwasher. A large window offers views of the ocean and palm trees, while a sliding glass door provides access to a balcony. Light-colored cabinets and a granite countertop enhance the space.

Home in Marathon

4.67 out of 5 average rating, 12 reviews

P76 - Meticulous 2 bed, 2 bath home with stunning

FreidaRating, 5 stars4 months ago

The views are breathtaking!! We loved every minute we spent here. Will absolutely stay again if it’s still available.

Guest favorite

Home in Big Pine Key

5 out of 5 average rating, 6 reviews

Cozy Waterfront Key Deer Retreat

KatherineRating, 5 stars1 month ago

Beautiful, Beautiful Beautiful did I say Beautiful. you won't be disappointed if you rent this house, so private and quiet. yes the neighbors are close but they weren't home our entire stay and we wouldn't have noticed if they were there, there was to much to do and see. So easy and close to a marina to put your boat in the water for 10$ each day In and Out. The Rooster was perfect for many dinners. Boondocks 10 minutes away for a little competitive putt putt, live music,and great food. Shopping galore Key West just 30 minutes away. Oh yes and the house was Beautiful, the beds were comfy, extremely clean and everything to make your vacation great is right here. The Key Deer are a bonus. Thank you Estrella we will be back.

Top guest favorite

Home in Key Colony Beach

5 out of 5 average rating, 30 reviews

Trip Around the Sun 2/2 + dockage & cabana club

KelliRating, 5 stars1 week ago

We absolutely loved our stay and would book this place again! The beds were incredibly comfortable! The house, especially the kitchen, is stocked with everything you will need and more! A boat launch is down the street within the Key Colony community, which was perfect! Peaceful back patio area with a pretty view on the canal. The house includes very impressive upgrades, so nicely done!!

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Vacation rentals in Pine Key

Top-rated vacation rentals in Pine Key

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Popular amenities for Pine Key vacation rentals

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