Family-friendly holiday rentals in Pinetop-Lakeside

The Happy Haven - Cozy Cabin w/fireplace

The Happy Haven is a newly decorated cabin in Showlow, Arizona! Just 3 hours from Phoenix, you and your family can escape to the white mountains to make new memories in the cool pines. The cabin is walking distance to hiking trails, a playground and only a mile from Fool's Hollow Lake! At the cabin enjoy drinking coffee on the deck, playing games and cooking in the well stocked kitchen. Enjoy the winter months with our cozy fireplace. NFL Sunday ticket included Follow us @happyhavenshowlow

Centrally Chic Bear Bungalow with AC & Hot Tub

A Stylishly Unique 3 BR 2BA Home; The Bear Bungalow provides amenities, comfort and convenience to enjoy White Mountains to the fullest! Located just behind a local Brewery, you're also within paws reach to quickly get to local restaurants, outdoor excursions, shops & more. Find Your retreat year-round for Families, Groups, Couples and those that want to bring a pooch with a fully fenced yard. TVs in every room, A/C, Hot Tub, Kid Friendly & custom artisan touches with quality furnishings abound.

#AzStoneCabin- Finest Luxury Cabin in Pinetop!

Are you ready for luxury in the tall pines? Experience the #AzStoneCabin, the finest luxury cabin in Pinetop- Lakeside! Tucked away in the woods of Pinetop with the most modern amenities and less than 30 minutes from Sunrise Ski Resort. This beautiful cabin sleeps up to 12 people with 3 bedrooms and a loft, full kitchen, and everything you need for your dream getaway in the woods. Book your trip to discover why many of our guests have said “This is the NICEST” AirBnB I have ever stayed at!”

Fun+Cozy Cabin | 2 Kings, Bunks, Slide, Game Room

Relax at this boho cabin 5 min from lake, packed with comforts, surrounded by treed lots on all sides! Two luxe king bedrooms, each with a quiet work space and 14" king mattress. A 3rd room with toys, books, and 6 incredible built-in bunks with premium Beddys for snuggly sleep. Spacious great room, with cozy fireplace and dining area for 10+. Ample cook’s kitchen, with island and pantry including amenities of home. Plus garage game room--ping pong, foosball, & arcade basketball! Rest + recharge!

The Bitty Bungalow

Welcome to The Bitty Bungalow, a charming tiny guest studio, perfect for those seeking cozy simplicity with all the comforts of home. It features a well-supplied mini kitchen, a deluxe redesigned bathroom, and a mini washer and dryer. My grandmother's antique roll-top desk and grandfather's original oil paintings complete the home's rustic look. While ideal for a solo or couple getaway, The Bitty Bungalow sleeps up to 6 guests, allowing families or groups to enjoy a modest retreat in the pines.

1/2 Acre Log Cabin w/ Fire Pit, Near Trails & Lake

Indulge in the tranquility of Pinetop at this 3-bed+loft, 1.5-bath log cabin surrounded by tall trees & nestled in a quiet community bordering the forest close to great dining, hiking, biking, fishing, skiing and more! The trailhead to Woodland Lake Park is located just steps from the property. Enjoy mornings sipping coffee on the porch while kids play on the play set. Spend nights w/ dinner on the grill, cozying up by the fireplace/TV, & roasting s'mores around the fire pit. High Speed WiFi!

Honey Bear’s Cabin in the White Mountains

This rental is right between Showlow and Pinetop. The woodsy cabin is perfect for an individual, couple as well as small group or family. The cabin is pet friendly. The upstairs loft is a hit with children and additional sleepers. Guests may access the clubhouse and it’s immenities. The two seating areas inside as well as outdoor firepit allow for diversity of gathering. The community is quiet, friendly and highly wooded. Smart tvs and starlink Wi-Fi, and Firepit. Central ac and heating.

Relax & Recharge in Cozy Pinetop 2BR Retreat

Your 2bed/2bath, was thoughtfully designed to feel like home. If you’re escaping for a weekend or a longer stay, our cozy retreat has everything you need to relax and recharge. Nestled in the heart of Pinetop-Lakeside, you’re close to Woodland Lake Park, and plenty of local gems to explore. Each room has its own A/C, heater, and fan, so you can enjoy peaceful, restful nights. Outside entertaining includes two covered decks and a patio set, perfect for soaking in the fresh mountain air.

Cozy Cabin in the Woods

Cabin is 400 square feet in size located 35 feet from owner's residence. Cabin is located near the end of a dead-end street, in a quiet neighborhood. Rainbow Lake can be accessed from the north side, an approximate 5-minute drive. Movie theater, grocery store and restaurants are within 10 minutes of the cabin. Blue Ridge High School is 2 miles from cabin. I take extra care to disinfect frequently touched surfaces between reservations in addition to my typical disinfecting routine.

The Monarch

Pets approved on a case by case basis! Please inquire. Escape the desert to enjoy the beauty and peace of the white mountains! The Monarch is conveniently located near local dining, lakes, and scenic hiking trails. Whether you are gathering to go skiing at Sunrise, reuniting with family for the holidays, or escaping the heat of the valley we are happy to accommodate your needs to make for a fun vacation! With a game room and other fun amenities, you will not be disappointed!

Twin Spruce Guesthouse

Available Year-Round, Conveniently Located in Downtown Pinetop in the White Mountains of Arizona. 512 sq ft., 1 bdr, 1 full bath. FAST NEW 5G WiFi. Walk to The Lion's Den, Charlie Clark's Steakhouse & Eddie's Country Store. Summer months bring Festivals and live music. Winter brings fun at Sunrise Ski Park, opens Dec 12th, 2025! Apache-Sitgreaves National Forest, just at the end of the street. Doggy Door, Pups welcome w/additional charge, send info with inquiry.

Shoreline Cabin w/ Kayaks *Channel Front*

Shoreline Tiny home located on the channel of Rainbow Lake! This 600 sq. ft. 1 bedroom, 1 bathroom cabin has 1 queen bed and a futon couch bed. Perfect for a couple or small family. In the warmer months, launch a kayak right off the backyard into the channel and paddle around the beautiful lake! Afterward, wind down for happy hour and enjoy the gorgeous outdoors around a campfire on the shore, or enjoy the large wrap around patio with a gas firepit and ample seating.