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Family-friendly holiday 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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Cottage in Florida

4.82 out of 5 average rating, 173 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.

6–13 Oct

$190 SGD per night

Guest favourite

Flat in Key West

4.98 out of 5 average rating, 449 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.

13–20 Apr

$463 SGD per night

Home in Cudjoe Key

4.9 out of 5 average rating, 104 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.

17–24 Jan

$544 SGD per night

Guest house in Miami

4.85 out of 5 average rating, 450 reviews

Tropical Elegence in Miami Brickell

You will appreciate your private entrance and space that Casa Roja has to offer. It is a stylish studio with a tropical elegance. The large room has a nice sitting area with a queen bed, sofa bed , desk, nice closet, large shower, microwave, kurig coffee maker and mini fridge. Located in one of Miami's best neighborhoods. RIght off I95 a short walk to Brickell Village ,Key Biscayne beaches, and Calle Ocho. Close to metrorail & a short uber to SOBE. Tropical paradise...location, location!

10–17 Aug

$149 SGD per night

Guest favourite

Home in Key West

4.97 out of 5 average rating, 206 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

28 Jul – 4 Aug

$555 SGD per night

Guest favourite

Flat in Miami

4.9 out of 5 average rating, 246 reviews

Tropical Bungalow Hideaway, Spacious Patio

Your studio in this peaceful bungalow is nestled in a lush tropical patio. It is separated from the rest of our home with private entrance in our little paradise! Want to start that book, rest or walk to the bay at dusk? Great for walking/biking. Children's and dog park nearby. Our village three blocks away has eateries, theatres, shops, gyms, boutiques, food markets, and sailing. Fridge/microwave/coffee/toaster. Private guest bath. Pets OK. Free parking.

9–16 Sep

$120 SGD per night

Guest favourite

Guest house in Coral Gables

4.96 out of 5 average rating, 262 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).

10–17 Aug

$127 SGD per night

Guest favourite

Home in Marathon

4.93 out of 5 average rating, 169 reviews

Beach, 70ft Dock, Entire Home, VACA-23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

26 Nov – 3 Dec

$419 SGD per night

Guest favourite

Home in Key Largo

4.9 out of 5 average rating, 347 reviews

Your Keys Getaway!

Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.

6–13 Feb

$254 SGD per night

Guest favourite

Boat in Miami

4.98 out of 5 average rating, 694 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 Key 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.

14–21 Jun

$187 SGD per night

Guest favourite

Guest suite in Homestead

4.99 out of 5 average rating, 247 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.

12–19 Jul

$110 SGD per night

Guest favourite

Flat in Key West

4.97 out of 5 average rating, 236 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

26 Mar – 2 Apr

$1,077 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Monroe County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Guest suite in Miami

4.87 out of 5 average rating, 456 reviews

Studio Apartment Dino's Place

7–14 Dec

$248 SGD per night

Guest favourite

Home in Homestead

4.93 out of 5 average rating, 357 reviews

Private Paradise between Miami & the Keys

28 Aug – 4 Sep

$454 SGD per night

Guest favourite

Townhouse in Marathon

4.83 out of 5 average rating, 122 reviews

Plunge Pool Villa on Blue Water Lagoon

25 Oct – 1 Nov

$354 SGD per night

Guest favourite

Apartment in Miami

4.92 out of 5 average rating, 161 reviews

Heart of Coconut Grove, pool. gym/sauna, park free

22–29 Jun

$170 SGD per night

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

17–24 Feb

$531 SGD per night

Guest favourite

Serviced apartment in Miami

4.92 out of 5 average rating, 156 reviews

Bay view, Coconut Grove, Mia

27 Feb – 6 Mar

$218 SGD per night

Guest favourite

Guest house in Coral Gables

4.85 out of 5 average rating, 300 reviews

Studio #1 hot jacuzzi Miami Center Beach

21–28 Aug

$202 SGD per night

Guest favourite

Serviced apartment in Miami

4.92 out of 5 average rating, 239 reviews

Private condo hotel at Four Seasons Brickell 34th

16–23 Jun

$501 SGD per night

Family- and pet-friendly home rentals

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 166 reviews

Flakey's

30 Nov – 7 Dec

$359 SGD per night

Guest favourite

Guest house in Miami

4.93 out of 5 average rating, 520 reviews

Artsy Cottage. Cute patio. LittleHavana & Brickell

4–11 Feb

$154 SGD per night

Guest favourite

Loft in Miami,Coconut Grove

4.89 out of 5 average rating, 156 reviews

The CoCo CABANA in coconut grove

18–25 Nov

$214 SGD per night

Guest favourite

Guest suite in Miami

4.89 out of 5 average rating, 196 reviews

Cozy Studio.

3–10 May

$132 SGD per night

Guest favourite

Flat in Miami

4.84 out of 5 average rating, 358 reviews

Enjoy A Tropical Getaway in Coral Gables

31 May – 7 Jun

$195 SGD per night

Guest suite in Miami

4.79 out of 5 average rating, 316 reviews

The JŪNGALŌW The Miami hidden Oasis 🌿

22–29 Aug

$175 SGD per night

Guest favourite

Townhouse in Key West

4.91 out of 5 average rating, 267 reviews

Sparkling clean. Newly Updated Family Friendly

8–15 Aug

$937 SGD per night

Guest favourite

Place to stay in Coconut Grove / Miami

4.89 out of 5 average rating, 345 reviews

Coconut Grove, Miami’s Tropical Hideaway

22–29 Jul

$280 SGD per night

Family-friendly home rentals with a pool

Guest favourite

Guest suite in Miami

4.95 out of 5 average rating, 243 reviews

"Casa Mia's" pool & BBQ bungalow

25 Aug – 1 Sep

$240 SGD per night

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 134 reviews

Beautiful open plan remodeled home in Key Colony

29 Jun – 6 Jul

$471 SGD per night

Guest favourite

Apartment in Key Largo

4.94 out of 5 average rating, 130 reviews

Private Condo, north Key Largo

25 Jul – 1 Aug

$654 SGD per night

Guest favourite

Villa in Marathon

4.95 out of 5 average rating, 119 reviews

4/3 Private Pool w Heater/Dock/Kayaks & more incl.

7–14 Dec

$1,204 SGD per night

Guest favourite

Townhouse in Key Largo

4.91 out of 5 average rating, 268 reviews

Casa Fish LLC

19–26 Dec

$322 SGD per night

Home in Key Colony Beach

4.88 out of 5 average rating, 113 reviews

Tiki Time

11–18 Nov

$294 SGD per night

Guest favourite

Townhouse in Key Largo

4.88 out of 5 average rating, 125 reviews

Key Largo House

8–15 Sep

$366 SGD per night

Guest favourite

Flat in Miami

4.97 out of 5 average rating, 126 reviews

0142 Skyline Serenity Apartment 1B/1B

13–20 Aug

$387 SGD per night

Destinations to explore