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Family-friendly vacation rentals in Monroe County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Monroe County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Home in Key Largo

4.84 out of 5 average rating, 426 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

Ocean views on Largo Sound, totally renovated home with large TV’s, spacious living area, 2 Large Balconies including roof top great for star gazing, all the amenities of home. Free use of kayaks at the house, Kayak John pennekamp state park steps away from front door. 27 foot boat available 4 all water activities Which I captain.Quiet private street close to all keys activities and restaurants. There is a downstairs space that on a very rare occasion is occupied by myself or family member

Rental unit in Key West

4.98 out of 5 average rating, 470 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 & BlueTooth stereo system with CD player & radio.

Villa in Marathon

4.95 out of 5 average rating, 123 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Cottage in Florida

4.83 out of 5 average rating, 184 reviews

Gateway to the Everglades, The Cottage

The Cottage is located about 45 min. South-West of Downtown Miami in the Redland Farming district along the eastern boarder of the Everglades National Park. Roughly the size of a two-bedroom apartment, it stands alone in the south-east corner of the property. Surrounded by trees, and many types of orchids, Bromeliads, and other exotic plants. Privet, and off the beaten path, the Cottage is perfect for those who wish to stay away from town, yet be close for day trips to most all attractions.

Townhouse in Duck Key

4.98 out of 5 average rating, 155 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Home in Homestead

4.93 out of 5 average rating, 375 reviews

Private Paradise between Miami & the Keys

My 4/3 home is in the area known as the "Gateway to the Keys". Enjoy a comfortable stay for 10 people in 4 bed rooms. Great place for families & travelers. Very comfy home, & the back yard has the feel of a true tropical paradise. Good WIFI My cleaning crew & I work very hard to keep it clean and sterile due to COVID. NO ADDITIONAL GUESTS & NO DJs. NO PARTIES. I RESERVE THE RIGHT TO ENTER THE HOME IF I FEEL THERE IS AN UNAUTHORIZED PARTY/EVENT. FINES WILL BE APPLIED FOR NOISE VIOLATIONS.

Guesthouse in Coral Gables

4.96 out of 5 average rating, 272 reviews

Cozy Cottage in quiet neighborhood.

Refurbished, SMALL DETACHED STUDIO (no kitchen, and sitting area is outside) with King sized bed, Wifi, microwave, kettle, French Press, small TV with premium channels, mini fridge, and private shower. Our peaceful backyard sanctuary is perfect for relaxing with a glass of wine (complimentary bottle upon arrival!) music,and/or a book. 2 miles to Miracle Mile restaurants / 12 miles to South Beach (20 - 30 mins.)/ Wynwood / Little Havana (3 miles).

Rental unit in Key Largo

4.83 out of 5 average rating, 317 reviews

Escape to the Keys!

Charming Keys Home located in a quiet residential neighborhood on the bay side. The house is on the 2nd floor with a large breeze balcony, great space to relax with a cup of coffee, tea or wine. Large fenced yard for sunbathing or for kids to run and play. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada.

Boat in Miami

4.98 out of 5 average rating, 726 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

Guest suite in Homestead

4.99 out of 5 average rating, 271 reviews

beautiful private king studio on nearly 5 acres

Close to Everglades National Park, Biscayne National Park, FL Keys, located in the Redland tropical agricultural area. This is a gated property with secure parking for campers, boats, trailers, etc. The studio is totally renovated with the highest quality of materials. Fruit is available to guests when in season and there is usually something in season during the year.

Home in Duck Key

4.89 out of 5 average rating, 161 reviews

4 Bed Sanctuary Villa w/ 35 ft Dock & Private Pool

My place is close to the heart of the FL keys. You’ll love my place because of the private tranquil pool in the backyard!. My place is good for couples, business travelers, families (with kids), and big groups. We also have a 35 foot dock that comes with the rental of the villa. You will need to procure trailer parking at Grassy Key Marina 2 miles South of the villa.

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Popular amenities for Monroe County family-friendly rentals

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Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in Coral Gables

4.85 out of 5 average rating, 319 reviews

Studio #1 hot jacuzzi Miami Center Beach

Condo in Tavernier

4.83 out of 5 average rating, 141 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

Rental unit in Miami

4.93 out of 5 average rating, 503 reviews

Deluxe 5 Stars ICON Brickell @37TH 2B/2B / Pool

Condo in Miami

4.92 out of 5 average rating, 166 reviews

Guest Favorite Coconut Grove, pool, gym, park free

Serviced apartment in Miami

4.96 out of 5 average rating, 195 reviews

2BD PH W/ Top Views & Five-Star Amenities | W 49

Home in Palmetto Bay

4.9 out of 5 average rating, 187 reviews

Hamilton House Tropical Oasis in Miami-Heated Pool

Guest suite in Miami

4.87 out of 5 average rating, 474 reviews

Studio Apartment Dino's Place

Condo in Tavernier

4.89 out of 5 average rating, 142 reviews

Spectacular 2 Bedroom with a beautiful ocean view.

Family- and pet-friendly home rentals

Cottage in Coconut Grove / Miami

4.9 out of 5 average rating, 356 reviews

Coconut Grove, Miami’s Hidden Tropical Gem

Home in Miami

4.89 out of 5 average rating, 217 reviews

Large heated Pool Home (Centrally Located)

Rental unit in Miami

4.88 out of 5 average rating, 130 reviews

OCEANFRONT VIEW. W Residences, FREE: POOL, Wi-Fi

Condo in Miami

4.91 out of 5 average rating, 186 reviews

YES! AMAZING APARTMENT - CORAL WAY

Townhouse in Key West

4.92 out of 5 average rating, 197 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

Rental unit in Miami

4.84 out of 5 average rating, 372 reviews

Enjoy A Tropical Retreat in Coral Gables

Guest suite in Cutler Bay

4.78 out of 5 average rating, 287 reviews

Private Waterfront Studio Paradise

Home in Coral Gables

4.87 out of 5 average rating, 119 reviews

Coral Gables Charm

Family-friendly home rentals with a pool

Serviced apartment in Miami

4.91 out of 5 average rating, 144 reviews

Exclusive Condo at Four Seasons + Free Valet & Gym

Townhouse in Key Largo

4.84 out of 5 average rating, 116 reviews

LIC. MGR. - 2/2 VILLA - OCEANFRONT BEACH RESORT!

Home in Key West

4.85 out of 5 average rating, 145 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

Rental unit in Miami

4.83 out of 5 average rating, 113 reviews

2/2 South Miami by MiamiVacations

Condo in Key Largo

4.99 out of 5 average rating, 103 reviews

Enjoy sunsets & sunrise in your home away home.

Townhouse in Key Largo

4.91 out of 5 average rating, 287 reviews

Casa Fish LLC

Condo in Miami

4.82 out of 5 average rating, 347 reviews

Beautiful Blue & Gold Studio with Ocean View

Condo in Key Largo

4.96 out of 5 average rating, 117 reviews

Kawama Suntastic @ Key Largo

Destinations to explore