
Beachfront holiday rentals in Big Pine Key
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Top-rated beachfront rentals in Big Pine Key
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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

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.

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 107,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 #107 and I also rent adjacent homes 111 and 109 in case you need more than one. We are 120 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.

Beachside Unit 14 - Brand New Kitchen and Bathroom
Unit 14 Details: Second Floor Unit, Walk-In Shower, King Bed and Queen Sized Sofa Pull-Out Bed, 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.”

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.

Stylish Anglers Retreat Poolside and Ocean U16
Embrace the charm of the Keys in our serene escape for couples or families. Nestled just steps from a heated pool and the ocean, this marine-themed retreat offers king comfort, a cozy sofa sleeper, and a screened balcony for intimate evenings. Dive into local adventures with available beach gear, or unwind in our airy space, boasting a fully equipped kitchen and tasteful decor. Ideal for those seeking a blend of relaxation and oceanic exploration, it's your perfect coastal haven.

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.

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts
Welcome to Ocean Oasis, your tropical haven in Marathon, Florida! Our stunning 2-bedroom, 2-bathroom condo is located at 501 E Ocean Dr, Marathon, FL 33050. Ocean Oasis offers the ultimate beachfront retreat, with a King-sized bed in the master bedroom and two full-sized beds in the second bedroom, comfortably sleeping six. The spacious balcony boasts breathtaking views of the ocean and pool, perfect for sipping morning coffee or enjoying a sunset cocktail. No Pets Allowed.

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

Beach Home and Boater’s Paradise Sombrero

Powell Family Resort

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

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

Charming Beach House directly ON the beach

Key West Luxury Houseboat at Yacht Club Resort

A slice of paradise!

Vibrant Beachfront Villa
Beachfront home rentals with a pool

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Island Vibes / 1BR + Den & 2 Balconies

Florida Keys Getaway w/ Stunning Ocean Views

Hyatt Beach House-Quiet Key West Spot!

Canal/Dock - Cabana Club - Pickleball - Remodeled

Oceanfront community 114 Anglers Reef Islamorada

Cabana Club Condo: Key Colony Beach, FL

2 Bdrm Oceanfront Complex Private Beach & Pool
Private beachfront home rentals

Peaceful Island Getaway in Islamorada! Parking!

Key West 2 BR Deluxe, Beach Front, sleeps: 6

Stunning tropical Ocean view condo

Hyatt Windward Pointe Resort: Beachfront Condo

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Oceanfront Key West Condo

Beachfront Condo on Coco Plum Beach w/heated pool

Coastal Key Colony Beach Condo, Oceanfront Complex
Quick stats about beachfront rentals in Big Pine Key

Nightly prices starting at
Big Pine Key holiday rentals start at ₹17,204 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
- Beachfront rentals Florida
- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- Conch Key
- Bahia Honda State Park
- Long Beach
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Southernmost Point
- Seven Mile Bridge
- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Boyd's Key West Campground
- History Of Diving Museum
- Ernest Hemingway Home & Museum
- Robbies Marina Of Islamorada
- Key West Lighthouse Museum




