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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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Apartment

4.82 out of 5 average rating, 156 reviews

2/2 Fully Updated Old Town Waterfront Corner Condo

Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW)

Guest favourite

Cottage

4.96 out of 5 average rating, 26 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

Guest favourite

Holiday home

4.96 out of 5 average rating, 52 reviews

Perfect Paradise

Perfect paradise is located in the heart of marathon. Only 9 minutes away from sombrero beach. Restaurant, supermarkets, ice cream, aquarium, and much more less than 7 minutes away. Public boat ramp is 5 minutes away. The house has plenty of parking spaces in the front to park your boat and cars. The home is fully stocked with everything you will need during your stay. For specific dates please message me first before booking so I may accommodate you to the dates that you would like to book.

Guest favourite

Home

4.97 out of 5 average rating, 238 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.

Guest favourite

Apartment

4.96 out of 5 average rating, 244 reviews

Amazing Ocean Front Views Key Colony Beach

Ocean front Florida Keys Studio Condo in Key Colony Beach with private balcony, heated pool and sandy beach. Continental Inn Unit #40 is a studio condo with a tropical interior featuring 2 queen beds and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Guest favourite

Home

5 out of 5 average rating, 21 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favourite

Home

4.97 out of 5 average rating, 180 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.

Home

5 out of 5 average rating, 5 reviews

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Home

4.84 out of 5 average rating, 25 reviews

( #3)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

#3: BIKINI BOTTOM 👙Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

Guest favourite

Home

4.9 out of 5 average rating, 107 reviews

Beautiful Renovated Home in Marathon, FL

Cozy home centrally located in the heart of Marathon with a ton of parking space for a boat or RV... Stay at ease in this family friendly neighborhood with lots of fun nearby (within 10 minutes) such as Sombrero Beach, FL Keys Aquarium, public boat ramp, kayaking, diving, restaurants and more!!! Licensed and inspected by the City of Marathon, Lic.#VACA-21-409

Townhouse

4.92 out of 5 average rating, 199 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a saltwater pool just steps away from the property. Perfect for families or groups of mature adults. All renters must be 25 or over or with a parent/guardian.

Holiday rentals for every style

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Villas

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Houses

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Convenient locations with everyday essentials

Popular amenities for Big Pine Key family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home

4.91 out of 5 average rating, 46 reviews

Key West Paradise

Guest favourite

Home

5 out of 5 average rating, 11 reviews

Waterfront paradise w/Private Pool-Dockage-Beach

Home

4.79 out of 5 average rating, 78 reviews

Waterfront Private Pool & Dock Near Sombrero Beach

Guest favourite

Home

4.94 out of 5 average rating, 102 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Guest favourite

Home

4.96 out of 5 average rating, 49 reviews

Paradise Ocean front Family Home Heated Pool.

Guest favourite

Home

4.98 out of 5 average rating, 53 reviews

Casa Blue Flamingo

Guest favourite

Home

4.86 out of 5 average rating, 14 reviews

Golf Coast Oasis

Home

4.8 out of 5 average rating, 86 reviews

Palm Breezes! Room for Everyone on the Ocean.

Family-friendly apartment rentals

Guest favourite

Flat

4.9 out of 5 average rating, 1,337 reviews

At Mine | Lovely Suite steps from Duval Street

Flat

4.78 out of 5 average rating, 226 reviews

The Green House ❀ Cool Shade

Guest favourite

Flat

4.98 out of 5 average rating, 479 reviews

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

Guest favourite

Flat

4.91 out of 5 average rating, 765 reviews

Duval Balcony Spanky's Retreat

Guest favourite

Flat

4.85 out of 5 average rating, 226 reviews

Studio Near Downtown - The Bartlum

Guest favourite

Flat

4.92 out of 5 average rating, 184 reviews

Duval St Apartment w/ Balcony w/parking Adult Only

Flat

4.85 out of 5 average rating, 222 reviews

#205 Key West Suites

Guest favourite

Flat

4.97 out of 5 average rating, 263 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Family-friendly apartment rentals

Guest favourite

Apartment

4.98 out of 5 average rating, 58 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Guest favourite

Apartment

5 out of 5 average rating, 25 reviews

Oceanfront and Sunrise Views!

Guest favourite

Apartment

4.9 out of 5 average rating, 115 reviews

Tropical Escape at Sunrise

Guest favourite

Apartment

5 out of 5 average rating, 5 reviews

*NEW* Kokomo Views-Pool/Beach

Apartment

5 out of 5 average rating, 10 reviews

Spacious - Excellent Key West Location

Apartment

4.87 out of 5 average rating, 93 reviews

Key Wes't Best- Upgraded condo 5 mins to Smathers

Apartment

4.61 out of 5 average rating, 239 reviews

Sunrise Suites Resort Key West, FL U #111 2bdr2bth

Apartment

4.85 out of 5 average rating, 106 reviews

Beachside Unit 37 - Come Relax on the Atlantic!

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

Total rentals
30 properties
Nightly prices starting at
€ 105 before taxes and fees
Total number of reviews
360 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore