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Kid-friendly holiday rentals in Big Pine Key

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Big Pine Key

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

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Cottage in Cudjoe Key

4.9 out of 5 average rating, 134 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!

12 – 19 Dec

$10,101 AUD total

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 186 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.

4 – 11 Aug

$2,673 AUD total

Tiny home in Big Pine Key

4.81 out of 5 average rating, 93 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

15 – 22 Aug

$1,325 AUD total

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.

10 – 17 Aug

$4,509 AUD total

Guest favourite

Condo in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

1 – 8 Sept

$4,140 AUD total

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!

4 – 11 Feb

$6,608 AUD total

Villa in Marathon

4.89 out of 5 average rating, 148 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!

15 – 22 Apr

$5,360 AUD total

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 124 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.

14 – 21 Oct

$5,075 AUD total

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 107 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.

14 – 21 Sept

$5,278 AUD total

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!!

11 – 18 Aug

$5,067 AUD total

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."

19 – 26 Dec

$4,991 AUD total

Guest favourite

Campervan/RV in Big Pine Key

4.93 out of 5 average rating, 41 reviews

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

17 – 24 July

$1,564 AUD total

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 kid-friendly rentals

Free parking on premises

Air conditioning

Child-friendly house rentals

Guest favourite

Home in Key Colony Beach

5.0 out of 5 average rating, 15 reviews

Coral House: 2/2 Waterfront in KCB w/ King Beds

13 – 20 May

$2,043 AUD total

Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

1 – 8 Oct

$2,807 AUD total

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 35 reviews

The Gulf Cottage at Marathon Key

29 June – 6 July

$1,898 AUD total

Guest favourite

Home in Marathon

4.98 out of 5 average rating, 85 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

24 – 31 Aug

$5,813 AUD total

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 15 reviews

Florida Keys Oceanside Utopia

24 – 31 Oct

$4,619 AUD total

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

20 – 27 Oct

$2,301 AUD total

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 35 reviews

Waterfront Tropical Oasis in the FL Keys

2 – 9 Nov

$4,831 AUD total

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

29 Mar – 5 Apr

$7,606 AUD total

Kid-Friendly apartment rentals

Guest favourite

Apartment in Key West

4.92 out of 5 average rating, 1053 reviews

At Mine | Lovely Suite steps from Duval Street

9 – 16 May

$2,966 AUD total

Guest favourite

Apartment in Key West

4.94 out of 5 average rating, 360 reviews

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

14 – 21 Sept

$3,027 AUD total

Guest favourite

Apartment in Key West

4.98 out of 5 average rating, 451 reviews

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

28 Apr – 5 May

$3,905 AUD total

Guest favourite

Apartment in Key West

4.97 out of 5 average rating, 237 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

3 – 10 Apr

$8,616 AUD total

Guest favourite

Apartment in Key West

4.9 out of 5 average rating, 212 reviews

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

20 – 27 Dec

$7,263 AUD total

Guest favourite

Apartment in Tavernier

4.89 out of 5 average rating, 437 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

14 – 21 July

$2,572 AUD total

Guest favourite

Apartment in Key West

4.91 out of 5 average rating, 707 reviews

Duval Balcony Spanky's Retreat

4 – 11 Dec

$5,581 AUD total

Apartment in Key West

4.8 out of 5 average rating, 127 reviews

Mango Hideaway steps off World Famous Duval street

26 Nov – 3 Dec

$6,098 AUD total

Child-Friendly Holiday Condos

Guest favourite

Condo in Key West

4.93 out of 5 average rating, 133 reviews

Beach Club Ocean Front 2BR Condo

21 – 28 Dec

$11,212 AUD total

Guest favourite

Condo in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

10 – 17 Nov

$2,920 AUD total

Condo in Key Colony Beach

4.81 out of 5 average rating, 108 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

10 – 17 Apr

$4,047 AUD total

Guest favourite

Condo in Key West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

22 – 29 Mar

$8,746 AUD total

Guest favourite

Condo in Key West

4.86 out of 5 average rating, 130 reviews

A Perfect Getaway

7 – 14 Oct

$5,255 AUD total

Guest favourite

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

28 Aug – 4 Sept

$3,171 AUD total

Guest favourite

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

1 – 8 Apr

$6,635 AUD total

Guest favourite

Condo in Tavernier

4.99 out of 5 average rating, 102 reviews

Ocean View Corner Penthouse | Ocean Pointe 5416

7 – 14 Sept

$4,452 AUD total

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
$151 AUD before taxes and fees

Destinations to explore