
Beachfront vacation rentals in Big Pine Key
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Top-rated beachfront rentals in Big Pine Key
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

Ocean Front Studio private Sandy Beach in Key West
Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

Exquisite Luxury Oceanfront Complex Key Colony
Beautifully renovated condo with all new kitchen & bathroom. #3 has 2 queen beds, fully equipped kitchen with full-size appliances & everything you need to cook and serve meals. Walk-in shower, free and reliable WiFi and SmartTV for watching your favorites. Enjoy stunning views of sunrise from our private beach and sunsets next door at Sunset Park. Heated pool, beach BBQs and tiki huts for guest use. We are centrally located to awesome Keys adventures just a few miles drive from the condo.

Boaters delight! 1 min to open water, Dock & Beach
Inquire for monthly discounts. The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

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.

Oceanside home 109, dock,kayaks,bikes,pool,fishing
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

SeaEsta! Bring your boat & 1 block to the beach!
Take a 1 Block walk to Sombrero Beach, dock your boat at this waterfront home or simply relax on the patio. 3 Bedrooms 3 baths. Large deck for cooking out. Direct access to the Atlantic. 65" TVs in all rooms. Enjoy your mornings by starting at our Coffee bar. Our home is fully furnished with all the essentials. We even include Kayaks, Bikes and Fishing Poles as well as Corn Hole and Giant Jenga. Boat Rental is offered at an additional cost. - VR License No: VACA -20-147

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

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.
Popular amenities for Big Pine Key beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

Powell Family Resort

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Coco Plum Beach Paradise w Heated Pool & Boat Slip

Walk to Beach, 90' Dock, Huge Pool, Kayaks

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Key West Luxury Houseboat at Yacht Club Resort
Beachfront home rentals with a pool

Stunning tropical Ocean view condo

Hyatt Windward Pointe Resort: Beachfront Condo

(# 6)Waterfront Beautiful 4 Bed 3 Bath Pool Home

RV In The Keys | Tropical Retreat

Coconut Palms in Marathon

Beachfront Condo on Coco Plum Beach w/heated pool

Florida Keys Getaway w/ Stunning Ocean Views

Calypso Cottage
Private beachfront home rentals

Oceanfront Sunrise Condo Private Beach Heated Pool

Spectacular 2BR Oceanfront Dog Friendly | Dock

Key Colony Beach Luxury Condo, New Modern Interior

Charming Beach House directly ON the beach

Modern Beachfront Steps to Beach/Pool, Key Colony

Sunny Beachfront Condo - Key Colony Beach & Pool

Paradise awaits.

Large 1 Bedroom Oceanview Condo With Two Balconies
Quick stats about beachfront rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at $247 CAD per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Big Pine Key rentals

4.8 Average rating
Big Pine Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Sombrero Beach
- Smathers Beach
- Long Beach
- Sea Oats Beach
- Bahia Honda State Park
- Conch Key
- Sunset Park
- Ernest Hemingway Home & Museum
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- The Turtle Hospital
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- Key West Lighthouse Museum
- Key West Butterfly & Nature Conservatory
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- Boyd's Key West Campground
- History Of Diving Museum
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