Family-friendly holiday rentals in Big Pine Key

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 158 reviews

Cancellation Deal: March 21 thru March 28

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Tiny home in Big Pine Key

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

4.93 out of 5 average rating, 75 reviews

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

4.94 out of 5 average rating, 153 reviews

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.93 out of 5 average rating, 122 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Guest suite in Key Colony Beach

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

4.99 out of 5 average rating, 120 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Campervan/RV in Big Pine Key

4.74 out of 5 average rating, 123 reviews

Tropical RV Getaway in Big Pine Key

Cozy RV is located on Big Pine Key where the endangered Key Deer roam. It is the perfect location! Located near a bike path that leads to restaurants, shops, bars, grocery store and beautiful waterfront park. Close to lots of Swimming, Snorkeling, Diving, Kayaking and Fishing. Just a short drive to Key West, Marathon, Bahia Honda State Park and National Key Deer Refuge. Great fishing spots nearby! Relax and unwind with a game of Connect 4 or Ring Toss in fenced in private backyard.

Condo in Key Colony Beach

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, 330 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

An aerial view of the waterfront area shows vibrant turquoise waters and lush greenery. The scene includes several residential buildings along the coastline and a nearby marina, with boats visible on the water and the horizon illustrating a scenic expanse.

4.93 out of 5 average rating, 215 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.84 out of 5 average rating, 114 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

4.9 out of 5 average rating, 453 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

4.92 out of 5 average rating, 106 reviews

Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.

Home in Summerland Key

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.

4.95 out of 5 average rating, 129 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Popular amenities for Big Pine Key family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.

4.98 out of 5 average rating, 56 reviews

Waterfront, Dock, Pool, Pickleball, near Key West!

4.86 out of 5 average rating, 219 reviews

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

Townhouse in Key West

Poolside Cottage #412

A light-filled living area features a comfortable seating arrangement with leather sofas and a large area rug. A television is housed within a white entertainment unit, flanked by decorative glass vases. Expansive sliding glass doors open to the outside, providing an airy ambiance.

4.95 out of 5 average rating, 61 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.81 out of 5 average rating, 294 reviews

Jan. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

4.95 out of 5 average rating, 371 reviews

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

4.82 out of 5 average rating, 100 reviews

Palm Breezes! Room for Everyone on the Ocean.

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

4.88 out of 5 average rating, 130 reviews

Waterfront Sanctuary in the Keys!

4.88 out of 5 average rating, 115 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

Villa in Paradise. Plunge pool. Middle of the Keys

Family- and pet-friendly home rentals

A spacious outdoor area is surrounded by tropical landscaping, featuring a BBQ grill and a hot tub. Comfortable lounge chairs are available under umbrellas, with a gravel walkway leading to various seating arrangements. Sunlight filters through the palm fronds, creating a relaxing atmosphere.

4.95 out of 5 average rating, 41 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

4.89 out of 5 average rating, 123 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

5 out of 5 average rating, 8 reviews

Dolphin Daydreams at Venture Out

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

4.95 out of 5 average rating, 133 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

4.95 out of 5 average rating, 80 reviews

Ocean~View*Pool*Dock*Kayaks*King Bed

A shaded tiki hut is situated on a stone patio beside a tranquil canal. The space is furnished with a table and chairs, surrounded by palm trees. Brightly colored kayaks are neatly arranged on a nearby dock, adding to the outdoor ambiance.

4.9 out of 5 average rating, 105 reviews

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

A spacious outdoor area features a tiki hut with a thatched roof, a swimming pool surrounded by lounge chairs, and a boat docked beside a canal. Lush palm trees provide shade, enhancing the tropical ambiance of the property. The home is visible in the background.

4.96 out of 5 average rating, 80 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

4.94 out of 5 average rating, 18 reviews

Boat in Key West

Houseboat in Key West

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 104 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Condo in Marathon

Canal View Condo w/ Pool, Balcony & Bar

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.

4.85 out of 5 average rating, 131 reviews

Beachside Unit 22 - Private Beach on Atlantic

5 out of 5 average rating, 3 reviews

A bright living area features a spacious sectional sofa and reclining chair, complemented by a large area rug with a wave pattern. A smart TV is mounted on the wall, and glass doors lead to a balcony with coastal views, framed by light blue curtains.

Condo in Marathon

The Turquoise Turtle-Beach/Pool

5 out of 5 average rating, 4 reviews

A tranquil pool area features lounge chairs arranged around a crystal-clear pool. Palms sway gently nearby, and a tiki bar with a roof can be seen in the background, overlooking calm waters. The sky transitions to a soft blue as evening approaches.

Apartment in Marathon

Marathon Studio on Lovely Gulf Front Resort

A serene canal view during sunset, showcasing vibrant orange and pink hues reflecting off the water. A concrete dock extends into the water, equipped with a fish cleaning station. A table and chairs are positioned nearby for relaxation and enjoyment of the picturesque scene.

5 out of 5 average rating, 9 reviews

Blue Heaven Waterfront Home

A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.

4.94 out of 5 average rating, 49 reviews

Rise And Shine On The Water

An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.

5 out of 5 average rating, 31 reviews

Bohemian Beach Bungalow