Family-friendly holiday rentals in Oldtown Scottsdale

Balcony-Pool View*Resort Feel*Walk Everywhere

Welcome to Old Town Scottsdale Traveler's Paradise!! You'll love this stylish yet comfy one bedroom condo with balcony overlooking the pool. Spend your mornings on the balcony with a fresh cup of coffee and your evenings with a fine glass of wine. Perfectly situated in a friendly community in Old Town Scottsdale, with the ability to walk to shopping, bars, spring training, the Culinary Festival, the Scottsdale Waterfront, boutiques, galleries, some of the hottest restaurants in town and more!

Walkable location, vibrant design, heated pool!

Steps to Old Town Scottsdale, our beautiful two-story townhouse, appropriately named Scott Place, is the perfect location for you and your guests to experience all the best Scottdale has to offer. This property has a resort-type feel as you experience many top amenities with Camelback Mountain as your backdrop. Located across the street from Fashion Square Mall and within walking distance to top rated restaurants, art galleries, and local attractions, your options are endless to enjoy yourself.

Designer OT Retreat 2B/2B | Com Pool/Hot Tub/Sauna

Welcome to this STUNNING designer retreat located in the heart of Old Town Scottsdale! Beautifully designed, this property offers comfort and luxury during your stay! The spacious layout, king beds, double sinks, and wine fridge make this unit so unique! Explore Old Town with the best shopping and dining options Arizona has to offer just a short walk away or relax by the resort style heated pool, hot tub, or dry sauna! Golf courses just around the corner and many more within a few minute drive!

Desert Oasis - 105, Heated Pool, Walk to Old Town

Arguably the best feature of the Palms is the location, snuggled smack dab in the middle of the Garden District with the walkability and proximity to everything you need. A quiet and private complex with a salt water pool and lush courtyard that is in the middle of the complex and just outside your sliding glass doors. Just minutes walk away is an endless mix of incredible restaurants of all types, resorts, coffee shops, convenience stores, nightlife, lounges, retail shops and entertainment.

4min Walk Old-Town Entertainment New Remodel+ POOL

Enjoy the AZ sun in our large play pool & hot tub ($150/per day heating fee) Golf turf in backyard. Comfortable outdoor furniture. 4 minute walk from the hottest restaurants, clubs, bars, lounges and luxury shopping @ Fashion Square Mall. Famous wine & art galleries in the heart of Old-Town Scottsdale. Lots of Hiking & parks a short drive away. Approx. 20min from the PHOENIX airport. Most convenient location in the area. It's one of the closest homes to everything happening in Scottsdale

Private Oasis. Walk to Old Town. Camelback Views.

🩵 OLD TOWN SCOTTSDALE BUNGALOW Your Perfect Getaway Awaits! Stay in a private home tailored for professionals, couples, families, and discerning guests who value a beautifully cared-for home, modern amenities, and one of the best walkable locations in Scottsdale. Work remotely with 758 Mbps Wi-Fi and a dedicated workspace, then shut the laptop and walk to Old Town Scottsdale. Easy access to restaurants, galleries, shopping, pubs, golf, hiking and the best experiences in the Valley.

Old Town Oasis | Heated Saltwater Pool & Hot Tub!

Escape to a world of luxury & tranquility at our Beach Cottage, an exquisite 3-bedroom, 2.5-bath retreat nestled in the heart of Old Town Scottsdale. Experience 2,500 sq ft of comfort & elegance, with a Saltwater Pool, Isla Margarita Elite Spa, and a delightful "She Shed" offering modern amenities & relaxation. From BBQs by the pool to cozy movie nights on a 75 inch HDTV, this charming Cottage promises an unforgettable blend of relaxation & fun. Book to experience this enchanting getaway.

Walk to Old Town ✴ 2 Masters ✴ Heated Pool & Spa

➳ Walk to the heart of Old Town in 2 minutes (Seriously, as good as it gets) ➳ Sprawling backyard with heated pool and spacious hot tub ➳ Endless outdoor living space with fire pit, propane BBQ grill and dining area ➳ Two generous master suites and three bathrooms ➳ Collapsible wall in the living room for indoor-outdoor living Looking for something a little different? I’ve got 8 more top-rated Scottsdale homes, all 5 minutes or less from Old Town. Click my host profile to explore!

The Kingsley|Custom|Heated Pool|Chef Kitchen|Chess

The Kingsley is a custom Scottsdale retreat by London Pierce Design featuring a private pool, oversized lawn chessboard, chef’s kitchen, and four beautifully designed bedrooms—three with en-suite baths. Located just minutes from Old Town Scottsdale, golf, and Sky Harbor Airport, the home offers open living spaces, shaded outdoor lounges, and garage parking for two vehicles. A stylish, design-forward retreat perfect for groups seeking comfort, space, and Scottsdale’s best location.

The Roosevelt, a villa in the heart of Scottsdale

Our 4-bedroom villa is nestled in a quiet, GATED community. The gorgeous furnished kitchen, HEATED* pool, and picturesque exterior spaces make this a dream getaway. Enjoy a relaxing stay with Tuft and Needle Mattresses, spa-like showers, an indoor fireplace, gorgeous baby grand piano, and modern classical styling. *HEATED pool is optional at an additional seasonal rate per day. Maximum rate of $100 per day. (Must notify the host 48 hours in advance to heat the pool.)

NewBackyardRenov | WALK 2 OLD TOWN•ShoppingDining

New backyard renovations are complete, featuring a putting green, turf, and a gazebo. Located across the street from Scottsdale's Entertainment District, the house is a short walk to Fashion Square Mall, along with other dining, entertainment, and shopping. The house features 3 bedrooms & 2 baths with a private pool, patio, dining, resting & relaxing space. It features an attached TV and Game room or second living room through a heated and cooled garage conversion.

Heated Pool | Modern Design | Private Oasis | Gym

🍹 Welcome to The Mai Tai, hosted by Happy Hour Homes. Featured in Dwell and formerly owned by a local modern architect, The Mai Tai is a one-of-a-kind mid-century retreat where thoughtful design, privacy, and outdoor living come together in the heart of South Scottsdale. Surrounded by custom steel walls, frosted glass, mature landscaping, and original architectural details, this private oasis blurs the line between indoors and outdoors.