Family-friendly holiday rentals in Key West

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 184 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

4.92 out of 5 average rating, 217 reviews

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

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, 122 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!

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

4.9 out of 5 average rating, 247 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to relax & enjoy waterfront living in this corner condo in historic Downtown Key West. Walk or bike everywhere—less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. On-site amenities include a heated pool, tiki bar & grills, parking, secure keyless entry, building elevator. Please note: The condominium dock will be under construction beginning April 27, 2026 for approximately 30 days; dock access will be unavailable and daytime construction noise is expected.

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

5 out of 5 average rating, 114 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

4.96 out of 5 average rating, 152 reviews

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

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.

4.97 out of 5 average rating, 111 reviews

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.

4.9 out of 5 average rating, 482 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!

4.98 out of 5 average rating, 533 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs & DVD players.

A private courtyard is displayed, featuring a hot tub, two chairs, and a small table. The entrance to the suite is visible with elegant French doors that open to the interior. Lush greenery enhances the tranquil ambiance, with a striped awning offering partial shade.

4.92 out of 5 average rating, 310 reviews

Starr's Suite - 2 person K Suite w/Private Spa!

Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.

4.91 out of 5 average rating, 197 reviews

A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.

Townhouse in Key West

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

4.91 out of 5 average rating, 116 reviews

Prime Downtown Key West Spot - Walk Everywhere!

Welcome to The Cozy Little Cottage! A REAL ISLAND GETAWAY IN KEY WEST!!! Nestled in the heart of Key West, The Cozy Little Cottage, welcomes you to a sanctuary of comfort and convenience. As your host, we're delighted to extend our warmest greetings and ensure your stay is nothing short of exceptional.

Popular amenities for Key West family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

4.91 out of 5 average rating, 160 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

5 out of 5 average rating, 3 reviews

Sunset Harbor 2 bed Ocean views!

4.96 out of 5 average rating, 23 reviews

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

Cottage in Cudjoe Key

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

4.86 out of 5 average rating, 72 reviews

A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.

Home in Cudjoe Key

Cozy 2 br/2 bath home in Cudjoe

A modern living area is presented with a comfortable grey sofa and two patterned chairs facing a large sliding door. Natural light fills the space, illuminating a textured wood coffee table and a side table with a lamp. A mounted television displays vibrant sunset imagery.

4.98 out of 5 average rating, 60 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.9 out of 5 average rating, 156 reviews

Tropical Escape at Sunrise

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 306 reviews

Affordable Beachfront Luxury Condo Sleeps 6

4.94 out of 5 average rating, 155 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 MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Family- and pet-friendly home rentals

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.

4.91 out of 5 average rating, 82 reviews

Cottage 30 min from Key West, free parking, pool

4.76 out of 5 average rating, 74 reviews

An open-concept interior features a full kitchen with modern appliances and ample cabinetry. A comfortable seating area is present, with a grey sofa and decorative yellow pillow. Natural light floods through the windows, highlighting the wooden beams and white walls that create a bright and welcoming space.

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

A light and airy living area features a modern blue sofa adorned with patterned throw pillows. A wooden coffee table sits in front, complemented by a tall indoor plant. A full-length mirror reflects the space, while natural light brightens the room through the patio door.

4.88 out of 5 average rating, 33 reviews

Duval Corner - Pet friendly with Balcony

4.97 out of 5 average rating, 205 reviews

The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

Home in Islamorada

Flakey's

5 out of 5 average rating, 11 reviews

A charming entrance is framed by lush tropical landscaping and vibrant foliage. A brick walkway leads through a white arched gate, guiding guests between two pastel-colored cottages. Lush palm trees and colorful plants create a welcoming atmosphere, enhancing the overall serenity of the space.

Home in Key West

Robinson Crusoe Cottage~ Delight In Island Vibes

4.91 out of 5 average rating, 106 reviews

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.

Home in Marathon

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

4.92 out of 5 average rating, 109 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!

4.95 out of 5 average rating, 129 reviews

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

Home in Key West

Paradise found

Family-friendly home rentals with a pool

4.77 out of 5 average rating, 13 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

The interior of the boat features wood-paneled walls and cozy seating areas. A plush gray sofa and an accent chair surround a star-patterned rug. A flat-screen TV is mounted on the wall, while the galley area is visible in the background, highlighting the boat's spacious layout.

4.77 out of 5 average rating, 52 reviews

Boat life with all the amenities

4.98 out of 5 average rating, 80 reviews

A busy street scene showcases Duval Street, with clear signage pointing in both directions. Lush palm trees line the sidewalks while pedestrians, enjoying the sunny weather, walk along the path. Colorful storefronts and flags create a vibrant atmosphere typical of Key West.

Home in Key West

Gorgeous Romantic Private Villa, Steps from Duval!

A shared pool area is showcased overlooking Garrison Bight Marina. Lounge chairs are arranged around the pool, with a thatched gazebo providing shaded seating. The marina is visible in the background, featuring moored boats and palm trees against a clear sky.

4.94 out of 5 average rating, 95 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

5 out of 5 average rating, 33 reviews

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.

Home in Key Colony Beach

Bohemian Beach Bungalow

An open-concept living area features wraparound seating in dark leather surrounding a polished wooden dining table. Abundant natural light filters through panoramic windows, reflecting off the rich wooden flooring. Tropical-themed wall decor and greenery enhance the inviting aesthetic. A well-equipped kitchen is visible in the background.

5 out of 5 average rating, 23 reviews

Sailboat Stay + Resort Amenities

4.81 out of 5 average rating, 175 reviews

A spacious studio apartment features a king bed with simple wooden bedside tables. A comfortable black sofa with decorative greenery is paired with a wooden coffee table. A dining area is located next to a light grey table, accented by soft lighting from overhead fixtures.

Apartment in Marathon

Knight's Key Suites Deluxe King Room w/ Kitchen