
Beachfront holiday rental in Big Pine Key
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Quick stats about beachfront rentals in Big Pine Key

Nightly prices starting at
Big Pine Key holiday rentals start at $314 NZD per night before taxes and fees

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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!
Top-rated beachfront accommodation in Big Pine Key
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

*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

Bright Cheery Condo, Ocean Views in Key Colony
Beautifully renovated condo in Key Colony Beach. with one king bed, well equipped kitchen with full-size appliances & everything you need to cook and serve meals. New A/C for great cooling. Renovated bathroom with walk-in shower, plenty of counter space and storage. Free & reliable WiFi with a private back balcony with chairs and table. Enjoy the heated pool & private sandy beach just steps away from your condo door. Sunset Park is next door, great for catching beautiful Florida Keys sunsets.

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

Cabana Club Condo: Key Colony Beach, FL
Located on the Atlantic Ocean in the middle keys. Accommodations for up to 10 people. Waking up to the sounds of ocean waves and the beautiful waters of the Florida Keys is breath taking. Very few are on a private beach. The unit is very spacious and well kept. Large master closet for storage. Private entrance and Cabana Club access during operating hours: ( Monday 10-5, Tuesday-Sunday 10-7 ). New furnishings, full kitchen, clothes washer and dryer. Minimum one week rental, seven nights.

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!

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

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.

P01 - New 3 bed, 3 bath with private pool
This beautiful new home offers 3 bedrooms, 3 baths and a comfortable open floorplan. Additionally, this property boasts and abundance of fabulous outdoor living space and is ideally located minutes from Coco Plum Beach. - Maximum Occupancy: 6 guests (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 3 vehicle max - 3 bedroom/3 bathroom

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

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

Coco Plum Beach Paradise w Heated Pool & Boat Slip

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

Key West Luxury Houseboat at Yacht Club Resort

SeaEsta! Bring your boat & 1 block to the beach!

Vibrant Beachfront Villa

Grassy Key Ocean Front Beach House
Beachfront home rentals with a pool

Grouper Getaway @ Ocean Isles Fishing Village

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Marathon 2BR Waterfront property on Resort

Private Beach in Marathons Key Colony Beach

Beach Front

Canal/Dock - Cabana Club - Pickleball - Remodeled

2 Bdrm Oceanfront Complex Private Beach & Pool

Paradise found! Sea-Esta Condo beach and pool.
Private beachfront home rentals

Spectacular 2BR Oceanfront Dog Friendly | Dock

Powell Family Resort

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Charming Beach House directly ON the beach

RV In The Keys | Tropical Retreat

Paradise awaits.

Florida Keys Getaway w/ Stunning Ocean Views

Calypso Cottage
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- Beachfront rentals Monroe County
- Beachfront rentals Florida
- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Southernmost Point
- Dolphin Research Center
- Conch Key
- History Of Diving Museum
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium
- Curry Hammock State Park





