Family-friendly vacation rentals in Big Pine Key

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Top-rated family-friendly rentals in Big Pine Key

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

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Guest favorite

Apartment 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.

Apr 13 – 20

R6,517 ZAR per night

Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 119 reviews

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

Our home is close to grocery stores, restaurants and dining, the beach, family-friendly activities, and public transport. You’ll love my place because of the high ceilings, the views, the location, the people, and the ambiance. Our place is good for couples, business travelers, and families (with kids). Included in the rental you'll have access to 4 bicycles for adults and 2 tandem kayaks and 2 paddle boards during your stay. We have a cooler, 2 beach umbrellas and 4 beach chairs for your use.

Jul 6 – 13

R13,648 ZAR per night

Guest favorite

Townhouse in Duck Key

4.98 out of 5 average rating, 141 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.

Oct 9 – 16

R8,843 ZAR per night

Superhost

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.

Jan 17 – 24

R7,661 ZAR per night

Guest favorite

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.

Apr 12 – 19

R10,942 ZAR per night

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 166 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Nov 30 – Dec 7

R5,056 ZAR per night

Guest favorite

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.

Nov 6 – 13

R6,287 ZAR per night

Guest favorite

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.

Sep 28 – Oct 5

R3,539 ZAR per night

Guest favorite

Apartment 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).

Mar 26 – Apr 2

R15,172 ZAR per night

Guest favorite

Townhouse in Marathon

4.83 out of 5 average rating, 122 reviews

Plunge Pool Villa on Blue Water Lagoon

YOUR TROPICAL PARADISE AWAITS. TWO BEDROOM 2 1/2 BATH SPA VILLA OVERLOOKING BLUE WATER LAGOON. SLEEPS 6 COMFORTABLY. GREAT FOR COUPLES, FAMILIES, HONEYMOONERS, FISHERMAN, GIRLS WEEKEND! 7 NIGHT MINIMUM IN HIGH SEASON. 3 NIGHT MINIMUM IN OFF SEASON.

Apr 22 – 29

R7,336 ZAR per night

Guest favorite

Apartment in Key West

4.94 out of 5 average rating, 359 reviews

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

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this Studio apartment is minutes from everything on the island. No cars are necessary, bikes & beach chairs are provided.

Sep 14 – 21

R4,871 ZAR per night

Guest favorite

Townhouse in Key West

4.91 out of 5 average rating, 267 reviews

Sparkling clean. Newly Updated Family Friendly

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a beautiful salt water pool just steps away from the property. Perfect for families or groups of mature adults.

Aug 10 – 17

R13,198 ZAR per night