Family-friendly holiday rentals in Clearwater

Coastal Escape: Heated Pool, Playground&Family fun

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

Family · Indoor spaces · Access

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

Kitchen · Family · Heating

Clearwater Gem! XL-Pool | Courts & More!.

Welcome to The Quazzi House, a private ½-acre tropical escape designed for fun, relaxation, and unforgettable memories. This unique 4BR / 3BA home features a 40-ft pool, private hot tub, pickleball & basketball court, and a spacious backyard perfect for families and groups. 📍 15 min to Clearwater Beach 📍 20 min to Tampa 📍 10 min to PIE Airport Ideal for large families or groups looking for an active, resort-style stay in sunny Fl! NO PARTIES — $1,000 fine & cleaning fee strictly enforced!

Kitchen · Family · Backyard

Retro home sleeps 10, Pets Welcome, beaches close

Step into 1960, skip the ordinary vacation rental and stay somewhere your family will actually remember. From the colorful retro diner and vintage décor to the fenced backyard and playful details throughout the home, every room was designed to make you smile, walk to Publix. Just minutes from Clearwater Beach, you'll enjoy modern comforts wrapped in a one-of-a-kind nostalgic Florida experience. This is Not just a place to stay it’s an experience you’ll talk about long after your vacation ends.

Kitchen · Indoor spaces · Pool

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Indoor spaces · Family · Amenities

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

Family · Kitchen · Check-in

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

Indoor spaces · Kitchen · Cleanliness

Tropical 4BR Escape with a Pool, < 7mi to beaches!

Experience the ultimate Florida getaway in this coastal retreat. Lounge beside the sparkling private pool or unwind beneath the covered lanai, complete with a 55” Smart TV, BBQ grill, and plenty of space for family dining. Just 4 miles from world-famous Clearwater Beach, you’ll be surrounded by endless upscale dining, chic bars, and boutique shopping—all within 2 miles. Baseball enthusiasts can stroll just 15 minutes to Spectrum Field, home of the Philadelphia Phillies Spring Training.

Kitchen · Indoor spaces · Decor

Spacious Key West Retreat, Fun 2 BR, Resort Pool

🌴 😎 Stunning Key West Style Retreat featuring: - Memory Foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts. Enjoy beach 🏄‍♂️ vibes decor in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Indoor spaces · Family · Outdoor spaces

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Indoor spaces · Family · Hospitality

Screened HTD Pool/SPA + Game RM + 15 Min to Beach

🏡 Bring the whole crew to a Clearwater retreat built for fun! 🎮 Newly added air-conditioned game room with pool, ping-pong, foosball, air hockey and a classic arcade cabinet. 🏊 Screened saltwater pool with built-in spa. 🌴 Fenced yard with cornhole, covered lanai and grill. 🛏️ This 5-bedroom, 3-bath home sleeps 16 and adds two living rooms, a full kitchen, WiFi, laundry and parking for four—all a short drive from Clearwater Beach and Indian Rocks Beach.

Family · Indoor spaces · Accuracy

Surf n Sand Studio Apartment by the Water 8

We were hit by 2 powerful hurricanes in the past month. As of now we are estimating to fully re-open on December 20th. In the meantime our upstairs rooms will stay open for guests who need a place to stay. Our rooms upstairs haven’t been damaged however, we will be working on fixing the rooms downstairs. Thank you for your understanding, and we really appreciate all the kind massages during this time.

Indoor spaces · Kitchen · Pool