Family-friendly vacation rentals in Cudjoe Key

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

4.89 out of 5 average rating, 177 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

FamilyKitchenBeach

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.

4.94 out of 5 average rating, 180 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

FamilyIndoor spacesView

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

4.97 out of 5 average rating, 129 reviews

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Indoor spacesKitchenHospitality

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, 323 reviews

SEPT/OCT. Save$Oceanfront 4 BIKE/2 Kayak KING Bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

FamilyIndoor spacesHot tub

Tiny home in Big Pine Key

A serene beach scene captures soft sands meeting clear waters under a bright blue sky. Lush palm trees frame the view, while visitors are seen enjoying the tranquil coastline and gentle waves. Green foliage and distant beach cabanas are also visible, enhancing the natural beauty.

4.88 out of 5 average rating, 132 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!

Indoor spacesFamilyHeating

4.81 out of 5 average rating, 114 reviews

A clear view of the sparkling waterway is framed by lush palm trees, with a blue boat docked on the left. The scene captures a seamless blend of greenery and water, while the surrounding landscape offers unobstructed access to open waterways.

Bungalow in Cudjoe Key

Cudjoe Key OCEANFRONT 2B/2B in gated community!!

Pets are not allowed. Sparkling clean and beautifully remodeled 2Bd/2Ba vacation home that features OPEN WATER views with great boating access to the ocean or gulf! This waterfront paradise features a 35' concrete seawall. There is a resort usage fee of $125 payable upon arrival to Venture Out. Pre-registration form of guests must be completed prior to stay or when checking in at the security gate. Check out my other property right next door! airbnb.com/h/islandtherapy46444432

Indoor spacesFamilyGrill

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, 129 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 a resort entry fee of $125 is charged per Whole group per stay directly to security upon entry into the park***

Indoor spacesFamilyBeach

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, 160 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

FamilyIndoor spacesCondition

4.86 out of 5 average rating, 610 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!

Indoor spacesFamilyDecor

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

4.96 out of 5 average rating, 211 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Indoor spacesFamilyParking

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.

4.83 out of 5 average rating, 111 reviews

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Indoor spacesKitchenLaundry

4.95 out of 5 average rating, 116 reviews

A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.

Home in Summerland Key

Waterfront Anchor 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 Haven 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!

Indoor spacesFamilyNearby

Popular amenities for Cudjoe Key family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A pair of outdoor chairs is positioned on a balcony, overlooking a vibrant canal. Palm trees and neighboring homes line the waterway, while a bright sky filled with fluffy clouds enhances the serene waterfront view.

4.86 out of 5 average rating, 126 reviews

Island Oasis ~ YOUR Paradise Awaits!

Indoor spacesKitchenParks

4.99 out of 5 average rating, 140 reviews

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.

Condo in Key West

Gorgeous Ocean View in Paradise, Close to Key West

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 101 reviews

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

Condo in Key West

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Indoor spacesFamilyHot tub

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.

4.89 out of 5 average rating, 18 reviews

Blue Heaven Waterfront Home

KitchenFamilyValue

A charming waterfront villa is framed by lush palm trees, featuring a spacious sandy area with vibrant landscaping. A boat is docked nearby, with soft clouds drifting across the blue sky, contributing to a serene outdoor environment.

4.97 out of 5 average rating, 29 reviews

Jan. Disc, Waterfront Retreat/Dock/Pool/golf cart,

KitchenIndoor spacesCleanliness

4.92 out of 5 average rating, 97 reviews

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

FamilyIndoor spacesAccess

Adirondack chairs are positioned on a coastal patio, providing views of the water and distant shoreline. Gentle waves reflect the sky, dotted with clouds. A palm tree sways lightly nearby, enhancing the serene environment by the water's edge.

4.97 out of 5 average rating, 95 reviews

Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW

KitchenIndoor spacesValue

A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.

4.81 out of 5 average rating, 37 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

KitchenFamilyCleanliness

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 129 reviews

A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.

Home in Key Colony Beach

Waterfront House with 37 ft Dock & Cabana Club

FamilyIndoor spacesCondition

4.94 out of 5 average rating, 158 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

KitchenFamilyBathroom

4.94 out of 5 average rating, 122 reviews

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

Home in Marathon

Coco Plum Waterfront Hideaway Home in Marathon

FamilyKitchenLocation

4.94 out of 5 average rating, 18 reviews

Blue Palms Retreat

FamilyKitchenCheckout

4.8 out of 5 average rating, 30 reviews

A covered outdoor dining area features a round table surrounded by six cushioned chairs. Scenic views of the turquoise water and distant shoreline are visible through the railing, with soft, natural light illuminating the space.

Bungalow in Cudjoe Key

Oceanfront Bungalow Venture Out

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 36 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)

FamilyIndoor spacesLaundry

4.94 out of 5 average rating, 17 reviews

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

Indoor spacesFamilyGetting around

Tiny home in Summerland Key

4.94 out of 5 average rating, 81 reviews

Cottage

KitchenIndoor spacesQuiet

Family-friendly home rentals with a pool

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.

4.99 out of 5 average rating, 75 reviews

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

KitchenFamilySkiing

A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.

4.88 out of 5 average rating, 42 reviews

Yellow Home - Receive $400 towards a Boat Rental!

Indoor spacesFamilyTV

The exterior of a yellow house is shown with multiple windows providing natural light. A bike stands parked on the gravel beside a garden featuring tropical plants. Stairs lead to the entrance, and the surrounding area is landscaped with pebbles.

4.87 out of 5 average rating, 39 reviews

Fisherman's Paradise Cudjoe Key

KitchenIndoor spacesBeach

A serene waterfront scene captures the reflection of clouds and colorful sunset hues on the calm water. Flanking the canal are inviting homes characterized by palm trees, with docks indicating easy access for boating enthusiasts. The peaceful setting suggests a tranquil atmosphere.

4.89 out of 5 average rating, 35 reviews

Pelican's Roost, Waterfront comfort at Venture Out

Indoor spacesKitchenParking

A charming cottage features light-colored siding and bright green shutters. A large palm tree adds tropical ambiance in the front yard, while a decorative welcome sign and colorful planter enhance the entrance. A smooth driveway leads to the home, complemented by sunny blue skies.

4.77 out of 5 average rating, 35 reviews

Wonderful Chalet - 20 miles from Key West

KitchenIndoor spacesBathroom

A colorful array of lounge chairs in yellow, green, and blue is positioned by a shared pool area. A thatched-roof cabana is visible, providing shaded seating near the water's edge. The lush surroundings and bright blue sky complement the inviting atmosphere.

4.94 out of 5 average rating, 33 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

Indoor spacesFamilyGetting around

4.95 out of 5 average rating, 21 reviews

Serenity Now Seaside Escape - Brand New Build!

Indoor spacesKitchenView

A newly constructed stilt home features a vibrant teal exterior and white railings. A staircase leads to the upper deck, where double doors open to the living space. A carport space is visible underneath, offering shaded parking and easy access to the entrance.