Holiday rentals in Big Pine

4.93 out of 5 average rating, 129 reviews

Cottage in Cudjoe Key

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.

Tiny home in Big Pine Key

4.81 out of 5 average rating, 195 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!

4.92 out of 5 average rating, 12 reviews

Perfect Couple Oasis!

You’ll treasure your time at this memorable location. New camper recently added to lot. Queen bedroom, bathroom, open living room with a full kitchen. Located on Big Pine Key, FL, between Marathon and Key West. Parking for 1 vehicle on lot, large vehicles will not fit. Key deer and roosters walk around park. Community pool and laundry facility. Great place to relax after fun in the sun or a night on the town! Renters must 25 years old or over. Community requires a rental form to be completed.

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

4.8 out of 5 average rating, 271 reviews

Boat in Marathon

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.

4.8 out of 5 average rating, 15 reviews

Home in Little Torch Key

Indulge yourself. It's heavenly in Little Torch

Welcome to our new 3 bedroom, 2 full bath home with a 60' dock on a gorgeous wide deep water canal. We are only 1,200' to the open waters of Pine Channel at the very southern end of Little Torch Key. Our home is thoroughly cleaned and sanitized before each visit. We have a guest friendly cancellation policy described in the additional house rules section. The living room, dining area and spacious kitchen open to a cozy rear porch and deck overlooking the serene canal. Enjoy ---....

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!

4.85 out of 5 average rating, 66 reviews

The Island Gypsy

Reconnect with nature at this unforgettable escape. Property butts up to the endangered Key deer refuge with almost daily sightings in the yard. Only 6 miles offshore is Looe key and the 3rd largest reef in the world. Our lot has parking for 2 vehicles with a outdoor dining area and large backyard for hanging out. The island gypsy is our 5th wheel which sleeps 4 with a queen bed, queen bunk beds and a sofa bed. Heated pool in the park and right across street from clubhouse.

4.91 out of 5 average rating, 320 reviews

Villa in Marathon

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!

4.97 out of 5 average rating, 159 reviews

Home in Cudjoe Key

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.

4.89 out of 5 average rating, 120 reviews

Houseboat in Marathon

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.

4.93 out of 5 average rating, 178 reviews

Home in Cudjoe Key

106 Newly Renovated House with Oceanview and Pool

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

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Other great holiday rentals in Big Pine

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars2 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!

4.6 out of 5 average rating, 25 reviews

Tiny home in RV park with pool

HermesRating, 5 stars4 weeks ago

everything was good and I recommend

4.8 out of 5 average rating, 5 reviews

Glamping in the Keys

JeffreyRating, 5 stars5 days ago

A1 place to stay! Ms Donna is a great host!

Holiday 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!

4.86 out of 5 average rating, 14 reviews

Home in Big Pine Key

Big Pine Key

BryanRating, 5 stars1 month ago

We had a great stay in Big Pine. We wanted a quiet area to use as our home base in the keys and the place and location were perfect. Snorkeling at horseshoe beach was fun. Easy to get down to key west for our snorkeling and boat trip. POP’s BBQ is great. Overall - a nice relaxing stay and the home was beautiful and well appointed. Thanks!

Townhouse in Little Torch Key

4.77 out of 5 average rating, 91 reviews

Waterfront 2BD / 2.5BTH Luxury Townhome

AlexRating, 5 stars1 month ago

Wonderful place to stay and great location for multiple key adventures throughout your stay. My family and I enjoyed the stay. We will definitely stay with little torch cottages again!