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

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.

Garden Oasis with Ocean Views | Pool & Beach
Uncover a hidden gem in our charming condo overlooking a tranquil garden with two unexpected side views of the ocean. It’s perfect for couples seeking a value-packed Keys getaway. A peaceful retreat, it is steps from the beach and pool, featuring a king bed, updated decor, and a screened balcony. With a full kitchen, it's your cozy base for exploring Marathon's beauty. Dive into relaxation or adventure, all while enjoying the comforts of our island home. Discover your Marathon haven today!

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.

Ocean front 1BR/1BA Suite w/ kitchen & living rm
1BR 1BA ocean front suite with a living room, kitchen and one bedroom. Doors that open to a balcony overlooking the Atlantic Ocean. Heated pool, hot tub, sun deck and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street and the most Southern Point. Located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. Free garage parking. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy central a/c.

*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.

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.

Oceanfront Breeze, Stunning Views, Beach/Pool
Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

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.

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

Colorful 2BR Oceanfront 4th-Floor | Balcony

Keys Breeze Ocean View Condo & Pool - Key Colony

Oceanfront Balcony King, Isla Bella, Beach Resort

Amazing Beachfront Studio w/ Stunning Gulf Views!

Oceanfront Key West Condo

Beachfront Condo on Coco Plum Beach w/heated pool

Coastal Key Colony Beach Condo, Oceanfront Complex

Seaport Serenity-Beach-Pool-King-BBQ-ExtraEntrance
Private beachfront home rentals

Oceanfront Sunrise Condo Private Beach Heated Pool

Beachside Unit 22 - Private Beach on Atlantic

Key Colony Beach Luxury Condo, New Modern Interior

Beachside Unit 14 - Brand New Kitchen and Bathroom

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Ocean Blue Condo, Key Colony Beach Heated Pool

A slice of paradise!

Tropical Beachfront Condo Key Colony Beach & Pool
Quick stats about beachfront rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at G$39,732 GYD 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Waterfront rentals Big Pine Key
- Rentals with a hot tub Big Pine Key
- Rentals with outdoor seating Big Pine Key
- Rentals with a fire pit Big Pine Key
- Rentals with a patio Big Pine Key
- Apartment rentals Big Pine Key
- Pet-friendly rentals Big Pine Key
- Rentals with pools Big Pine Key
- Family-friendly rentals Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Smoking-friendly rentals Big Pine Key
- Condo rentals Big Pine Key
- House rentals Big Pine Key
- Rentals with a kayak Big Pine Key
- Rentals with beach access Big Pine Key
- Rentals with a washer and dryer Big Pine Key
- Villa rentals Big Pine Key
- Cottage rentals Big Pine Key
- Beachfront rentals Monroe County
- Beachfront rentals Florida
- Beachfront rentals United States
- Ernest Hemingway Home & Museum
- Key West Lighthouse Museum
- Sombrero Beach
- Smathers Beach
- The Turtle Hospital
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Conch Key
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Seven Mile Bridge
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground




