
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.

Key Colony Beach Luxury Condo, New Modern Interior
Private studio condo at Key Colony Beach with a private balcony, heated pool and sandy beach. Unit #15 was recently renovated and offers one comfy King size bed and a fully equipped kitchen with essentials (stove, oven, toaster, microwave, blender, fridge, cooking utensils). Wifi, Amazon Echo and a TV. Enjoy a short walk to Sunset Park next door to experience a stunning Florida Keys sunset. Guests also have access to a private beach with lounge chairs, patio tabales, tiki huts, and BBQ grills.

RV In The Keys | Tropical Retreat
Tropical retreat in the heart of Florida Keys. Relax in this fully furnished private & clean RV with parking just 30 miles from Key West. Enjoy breezy indoor/outdoor living with a fold-down patio, 2 TVs, full kitchen, bathroom, pantry. Outside seating g with awning. Nestled in a local RV park w/ pool, fish station, and coin laundry. Vacation here & swim in the ocean —Next to Pine Channel in Big Pine Key and 10 miles to Bahai Honda State Park. Walk to groceries, Walgreens, restaurants. Staycation

*NEW* Private Beach, pool & fully loaded kitchen
Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. 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.

Private Beach in Marathons Key Colony Beach
Atlantic Ocean location with a beautiful ocean view. The beach is private for sunbathing, fishing, diving, and snorkeling. The sea life off the beach is abundant. Watching the boats come in and out of Vaca Cut is very cool. In addition to the onsite pool there is a Tiki Hut, beachside barbecue area, and a beautiful grass lawn. Being on the third floor offers beautiful ocean views. Please see my host guidebook for detailed info on a few of the local attractions including fav restaurants.

Grouper Getaway @ Ocean Isles Fishing Village
Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

Oceanside home 111, 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 #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 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.

Paradise found! Sea-Esta Condo beach and pool.
Sea-Esta is located on the Atlantic Ocean with a private white sandy beach. If the ocean isn’t calling you, Sea-Esta by the heated pool to cool off and work on your tan. Or, Sea-Esta in your master bedroom with its king-size bed and ocean views from its small deck. Sea-Esta under the shade of the lush landscaping that Sea Isle has to offer. Walking distance to Sunset Park, 3 par golf course, pickleball, tennis, bocce ball, and playground. Safe bike/walking paths throughout Key Colony.

*NEW*May the Surf Be With You-Florida Keys Retreat
Beautiful 2 bedroom, 2 bath condo in Key Colony Beach, Marathon FL. This spacious retreat features a king bed, a queen bed, and bunk beds, perfect for families or groups. Enjoy access to a private beach and a refreshing pool, all just steps from your door. Centrally located near restaurants, fishing, and the best of the Florida Keys, this condo offers the perfect mix of comfort and island relaxation. -No Pets are allowed. -No Smoking allowed. -You must be 25 years or older to rent.

Hidden Beach unit 1 The Perfect Place to stay
This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Oceanview Retreat w/Pool Steps Away From Beach #14
Discover our inviting 1-bedroom condo in Marathon, a serene retreat with stunning ocean views from a screened balcony. Featuring a king bed, updated amenities, and cozy living spaces, this condo is ideal for those seeking a beachside experience. Steps from a rare sandy beach and adjacent to Coco Plum Beach, it's perfect for water sports or relaxation. Enjoy updated furnishings, a king-sized bed, and easy pool and tennis court access for a memorable Florida Keys adventure.

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

Beach Home and Boater’s Paradise Sombrero

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

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

Charming Beach House directly ON the beach

Key West Luxury Houseboat at Yacht Club Resort

New Private 4/3 Single Family - Kayaks & Bicycles+

Vibrant Beachfront Villa
Beachfront home rentals with a pool

Wreckers House King Room - Adults Only

Oceanfront Breeze, Stunning Views, Beach/Pool

Key West paradise- 3 night stay Minimum

Oceanfront Balcony King, Isla Bella, Beach Resort

Port Antigua NEW lux apart

Amazing Beachfront Studio w/ Stunning Gulf Views!

Tropical Beachfront Condo Key Colony Beach & Pool

Beachside Unit 37 - Come Relax on the Atlantic!
Private beachfront home rentals

Beachside Unit 22 - Private Beach on Atlantic

Beachside Unit 14 - Brand New Kitchen and Bathroom

Keys Breeze Ocean View Condo & Pool - Key Colony

Modern Beachfront Steps to Beach/Pool, Key Colony

Sunny Beachfront Condo - Key Colony Beach & Pool

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Ocean Blue Condo, Key Colony Beach Heated Pool

A slice of paradise!
Quick stats about beachfront rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at R3,017 ZAR per night before taxes and fees

Verified guest reviews
Over 230 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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- Beachfront rentals Monroe County
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- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Conch Key
- Bahia Honda State Park
- Long Beach
- Florida Keys Aquarium Encounters
- Sunset Park
- Seven Mile Bridge
- Dolphin Research Center
- Southernmost Point
- Fort Zachary Taylor Historic State Park
- Key West Butterfly & Nature Conservatory
- Robbies Marina Of Islamorada
- Key West Lighthouse Museum
- Ernest Hemingway Home & Museum
- The Turtle Hospital
- Boyd's Key West Campground




