Beachfront vacation rentals in Big Pine Key

A spacious sleeping area includes a king-sized bed with crisp white bedding and decorative pillows. Metal fish sculptures adorn the wall, complemented by two bedside lamps. A dark sectional sofa is positioned nearby, creating a comfortable seating area for relaxation.

4.92 out of 5 average rating, 310 reviews

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.

Tiny home in Big Pine Key

A well-maintained 28-ft Grey Wolf RV is parked on a gravel lot, surrounded by tropical greenery. Two lounge chairs are positioned on a green patch of grass, creating a relaxing outdoor seating area. Sunshine filters through the clouds, adding a bright ambiance to the scene.

4.81 out of 5 average rating, 21 reviews

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

4.88 out of 5 average rating, 113 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

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.

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 23 reviews

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.

4.98 out of 5 average rating, 55 reviews

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.

4.75 out of 5 average rating, 4 reviews

A bright and inviting living area showcases a comfortable seating arrangement of a sofa and chairs, with tropical-patterned accents. A glass dining table is set to accommodate four, while a large sliding door opens to the screened balcony, revealing views of lush greenery.

Condo in Marathon

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!

Lounge chairs are positioned on the grass near the ocean, surrounded by palm trees. A soft gradient of colors in the sky, transitioning from pale pink to light blue, is visible above the tranquil waters. Rocky shoreline meets the beach, creating a peaceful environment.

4.96 out of 5 average rating, 49 reviews

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.

4.77 out of 5 average rating, 13 reviews

A three-story oceanfront home is showcased, featuring a spacious outdoor deck and private pool area. Lush palm trees surround the property, and a sandy pathway leads to the entrance. The home is painted in a light color, blending with the bright blue sky.

Home in Cudjoe Key

Latitudes-Ocean Front Pool

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers. This home is priced based on the number of guests.

5 out of 5 average rating, 10 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

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!

4.94 out of 5 average rating, 35 reviews

A spacious balcony provides views of the ocean and pool area, with comfortable seating arrangements including two chairs and a table. The gentle wave pattern of the sea is visible in the background, along with a poolside and a nearby pier.

Condo in Marathon

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.

4.97 out of 5 average rating, 111 reviews

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

Condo in Key West

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.

A tiki hut with a thatched roof provides shaded seating, surrounded by tall palm trees. Clear blue waters extend to the horizon, while the sandy beach features white lounge chairs arranged nearby, creating a serene coastal setting.

4.85 out of 5 average rating, 115 reviews

Beachside Unit 37 - Come Relax on the Atlantic!

Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, 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. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.

Popular amenities for Big Pine Key beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

New place to stay

Beach Home and Boater’s Paradise Sombrero

The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.

4.9 out of 5 average rating, 41 reviews

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

An aerial view of a canal-front home showcases a spacious backyard with a private swimming pool. A long dock extends into the water, bordered by lush greenery. The surrounding neighborhood features a mix of single and multi-story homes, with palm trees dotted throughout the landscape.

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

5 out of 5 average rating, 4 reviews

A sunlit deck features white lounge chairs positioned towards a private beach and ocean view. A thatched-roof tiki hut provides shade, while a hammock is nestled nearby among greenery. The calm waters reflect the blue sky, enhancing the serene coastal setting.

Home in Islamorada

Charming Beach House directly ON the beach

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

5 out of 5 average rating, 49 reviews

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

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.83 out of 5 average rating, 270 reviews

Key West Luxury Houseboat at Yacht Club Resort

A private backyard showcases a tranquil pool surrounded by a stone deck. Comfortable lounge chairs are positioned for relaxation, with a vibrant float placed in the water. The blue exterior of the house enhances the outdoor space under a partly cloudy sky.

4.93 out of 5 average rating, 84 reviews

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

A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.

Townhouse in Duck Key

4.81 out of 5 average rating, 203 reviews

Vibrant Beachfront Villa

Beachfront home rentals with a pool

4.85 out of 5 average rating, 279 reviews

A spacious room features a large wooden bed with crisp white bedding. Light from a sliding glass door illuminates the space, revealing a view of palm trees and the outdoors. A ceiling fan and two bedside lamps provide ambient lighting, with a small desk and seating area visible.

Hotel room in Marathon

Wreckers House King Room - Adults Only

4.93 out of 5 average rating, 263 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

An outdoor balcony space features a round table surrounded by two armchairs and a spacious sofa, all in light wicker with patterned cushions. Palm trees frame the serene ocean view, creating a relaxing retreat.

Hotel room in Marathon

5 out of 5 average rating, 5 reviews

Oceanfront Balcony King, Isla Bella, Beach Resort

Apartment in Marathon

Ocean front with private beach and pool!

A private pool area features two connected sections, including a spacious swimming area and a jacuzzi. Surrounding palm trees and well-maintained landscaping create a serene atmosphere. Bright blue skies and fluffy clouds reflect on the water's surface, inviting relaxation.

Vacation home in Islamorada

Port Antigua NEW lux apart

A sandy beach scene is depicted with palm trees swaying gently in the breeze. A rainbow arches over the turquoise sea, while a wooden dock stretches into the water. Two lounge chairs are positioned near the shoreline, creating a relaxing outdoor space.

Hotel room in Layton

4.59 out of 5 average rating, 17 reviews

Amazing Beachfront Studio w/ Stunning Gulf Views!

4.81 out of 5 average rating, 26 reviews

An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.

Condo in Key West

Oceanfront Key West Condo

A bright and airy studio room features two queen-sized beds with crisp white bedding and anchor-themed decorative pillows. Light blue accents are present throughout, complemented by coastal artwork on the walls. Large windows allow natural light to fill the space, enhancing its serene atmosphere.

4.92 out of 5 average rating, 331 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

Private beachfront home rentals

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 227 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.86 out of 5 average rating, 134 reviews

Beachside Unit 22 - Private Beach on Atlantic

4.85 out of 5 average rating, 106 reviews

Beachside Unit 14 - Brand New Kitchen and Bathroom

A modern living area is displayed with light-colored walls and a wood-style floor. A comfortable sectional sofa and vibrant blue seating surround a circular table. A flat-screen television mounts on the wall, and natural light enters through two windows, enhancing the bright atmosphere.

4.96 out of 5 average rating, 263 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

A spacious studio condo layout is featured, showcasing two queen beds with light-toned beddings. A comfortable seating area is included with a dark sofa and an accent chair. Decorative wall art and a potted plant enhance the fresh and minimalist style of the room.

4.91 out of 5 average rating, 132 reviews

Sunny Beachfront Condo - Key Colony Beach & Pool

Apartment in Key Colony Beach

A view from a balcony reveals a calm canal with a clear blue sky above. Palm trees sway gently in the breeze, and various boats are docked along the waterfront. The setting showcases a peaceful neighborhood with homes lining the opposite shore.

4.89 out of 5 average rating, 9 reviews

A slice of paradise!

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.88 out of 5 average rating, 146 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

A well-maintained lawn leads toward the ocean, with palm trees swaying gently in the breeze. Beach chairs are arranged along the shore, offering a view of the sparkling water under a partially cloudy sky.