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Kid-friendly holiday rentals in Big Pine Key

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Big Pine Key

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

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Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 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!

3–10 Mar

₹72,583 per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 185 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

12–19 Oct

₹18,122 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

₹33,326 per night

Guest favourite

Boat in Islamorada

4.9 out of 5 average rating, 171 reviews

HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

11–18 Sep

₹14,498 per night

Guest favourite

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. 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 dock and enjoy the underwater scenery!

6–13 Sep

₹39,885 per night

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

29 Oct – 5 Nov

₹28,501 per night

Villa in Marathon

4.89 out of 5 average rating, 145 reviews

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!

3–10 Apr

₹36,764 per night

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 122 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.

7–14 Oct

₹30,341 per night

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill 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.

24–31 Aug

₹33,946 per night

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

22–29 Aug

₹19,391 per night

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 125 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! 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!!

28 Jul – 4 Aug

₹41,382 per night

Guest favourite

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise at Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

15–22 Jan

₹33,747 per night

Holiday rentals for every style

Get the amount of space that is right for you

Houses

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

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Popular amenities for Big Pine Key family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Big Pine Key

4.92 out of 5 average rating, 13 reviews

Home in Big Pine Key

9–16 Feb

₹28,818 per night

Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

1–8 Oct

₹18,736 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

8–15 May

₹13,191 per night

Home in Cudjoe Key

4.86 out of 5 average rating, 43 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

10–17 Oct

₹40,720 per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 34 reviews

The Gulf Cottage at Marathon Key

6–13 Jul

₹12,633 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

₹67,220 per night

Guest favourite

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

4–11 Oct

₹32,191 per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 36 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

10–17 Nov

₹40,930 per night

Family-friendly apartment rentals

Guest favourite

Flat in Key West

4.92 out of 5 average rating, 1036 reviews

At Mine | Lovely Suite steps from Duval Street

28 Jul – 4 Aug

₹23,687 per night

Guest favourite

Flat in Key West

4.98 out of 5 average rating, 450 reviews

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

26 Apr – 3 May

₹27,776 per night

Guest favourite

Flat in Key West

4.97 out of 5 average rating, 237 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

14–21 Apr

₹61,304 per night

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 359 reviews

Studio Blu - Key West, FL - Hip Studio in Old Town

14–21 Sep

₹21,041 per night

Guest favourite

Flat in Key West

4.9 out of 5 average rating, 212 reviews

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

29 Mar – 5 Apr

₹46,626 per night

Flat in Key Largo

4.84 out of 5 average rating, 238 reviews

Key's Cottage Escape

1–8 Nov

₹15,097 per night

Flat in Key West

4.81 out of 5 average rating, 126 reviews

Mango Hideaway steps off World Famous Duval street

8–15 Aug

₹27,205 per night

Guest favourite

Flat in Tavernier

4.89 out of 5 average rating, 434 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

14–21 Jul

₹16,370 per night

Family-friendly apartment rentals

Guest favourite

Apartment in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

9–16 Aug

₹17,160 per night

Guest favourite

Apartment in Key West

4.93 out of 5 average rating, 132 reviews

Beach Club Ocean Front 2BR Condo

1–8 Dec

₹77,776 per night

Guest favourite

Apartment in Key West

4.86 out of 5 average rating, 129 reviews

A Perfect Getaway

8–15 Dec

₹37,100 per night

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

8–15 Nov

₹66,868 per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

30 Aug – 6 Sep

₹22,321 per night

Guest favourite

Apartment in Tavernier

4.88 out of 5 average rating, 228 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

30 Jul – 6 Aug

₹20,734 per night

Guest favourite

Apartment in Key West

4.83 out of 5 average rating, 243 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

27 Apr – 4 May

₹39,800 per night

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

11–18 Dec

₹34,846 per night

Quick stats about holiday rentals that are kid-friendly in Big Pine Key

Total rentals
20 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
280 reviews
Nightly prices starting at
₹8,344 before taxes and fees

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