Pet-friendly holiday rentals in Big Pine Key

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

The Snapper House is a spacious 3/2.5 bed/bath duplex with 45' of canal dock frontage, also Includes the Cabana Club with large pool (food/drinks for purchase) and ocean facing beach. Awning extends to dock from sliding doors. TV package includes 100+ channels Each bedroom and living room has a full size flat screen TV. For best WIFI reception, an extender is available and should be used when in the back bedrooms, it's name is the same as the main house with an "ext" at the end (same pw).

Boater’s Paradise 3br/2.5ba at Coral Lagoon

*PLEASE NOTE* Villa slips/canal are under construction until Dec 2025. Please inquire before booking. Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun.

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.

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

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!

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

Starr's Suite - 2 person K Suite w/Private Spa!

Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.

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.

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.

Beautiful Renovated Home in Marathon, FL

Cozy home centrally located in the heart of Marathon with a ton of parking space for a boat or RV... Stay at ease in this family friendly neighborhood with lots of fun nearby (within 10 minutes) such as Sombrero Beach, FL Keys Aquarium, public boat ramp, kayaking, diving, restaurants and more!!! Licensed and inspected by the City of Marathon, Lic.#VACA-21-409

Sunset Villa in Duck Key

Relax and unwind with the family on the patio of this scenic villa overlooking Tom's harbor and Hawks Cay Marina, where you can choose to keep your boat with confidence and ease of access by contacting the marina directly.