Family-friendly holiday rentals in Clearwater Beach

4.97 out of 5 average rating, 153 reviews

The exterior of a charming blue beach house is surrounded by lush palm trees and vibrant landscaping. A spacious front yard features a green lawn and neatly trimmed bushes, while a driveway accommodates parked vehicles. Sunlight filters down, creating a warm atmosphere.

Home in Clearwater Beach

THE HOUSE - 32 Steps to the Beach - Beautiful Clea

House sleeps 6 - Private patio and Hot Tub, Wifi, Grill . '32 Steps to the Beach' is a charming and cozy Clearwater Beach retreat in a TOP LOCATION. The pristine Gulf Beach is just across the street! We also have a Cottage at the same address and they can be rented separately or together. Covid-19 UPDATE - See below. To book the House & Cottage or the Cottage on its own please see the links to their descriptions at the right of this page. THE HOUSE is a tastefully decorated, upscale

Indoor spacesFamilyPets

5.0 out of 5 average rating, 177 reviews

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

Home in Palm Harbor

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

FamilyKitchenHospitality

4.91 out of 5 average rating, 204 reviews

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

FamilyIndoor spacesCheck-in

Bungalow in Indian Shores

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

KitchenFamilyAmenities

4.97 out of 5 average rating, 206 reviews

Townhouse in Indian Rocks Beach

A multi-story coastal condo stands proudly along the shoreline, with a light-colored exterior that complements the blue ocean in the background. Tropical landscaping encircles the entrance, while the private parking area is visible in front. The sandy beach is just a short walk away.

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U2 ♥

✳ DAYDREAMERS ✳ Indian Rocks Beach condo offers convenient access to white sand beaches of the Gulf. Watch as dolphins swim into the sunset and beachcombers look for shells and buried treasure. With a coastal beachy atmosphere, this beauty will take you out of your element. This home features ultra comfy bedding for maximum rest & relaxation. So dream a little dream, while relaxing your day away. The unique coastal design compliments all of the things IRB has to offer. PETS MUST BE APPROVED

Indoor spacesKitchenCheck-in

4.94 out of 5 average rating, 152 reviews

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

4.98 out of 5 average rating, 182 reviews

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.

KitchenFamilyLong stay

4.94 out of 5 average rating, 102 reviews

PVT Heated Pool + Spa + Game Room, Dream VacaHome

🏊Private saltwater heated pool with built-in spa. 🎮Newly added air-conditioned game room with pool, ping-pong, foosball, air hockey and a classic arcade cabinet. 🌴 Fenced yard with cornhole, covered lanai and grill. 🛏️ This 5-bedroom, 3-bath home comfortably hosts up to 10 guests, with two living rooms, a full kitchen, WiFi, laundry and parking for four.—all a short drive from Clearwater Beach and Indian Rocks Beach. 🏡 Bring the whole crew to a Clearwater retreat built for fun!

Indoor spacesFamilyCheck-in

Townhouse in Clearwater Beach

A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.

Waterfront Beach House Steps Away from #1 Beach!

Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

Indoor spacesFamilyWalkability

5.0 out of 5 average rating, 152 reviews

4.93 out of 5 average rating, 122 reviews

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

FamilyIndoor spacesHospitality

4.99 out of 5 average rating, 214 reviews

A panoramic view of the inter-coastal waterway features clear turquoise waters and a marina with multiple boat docks. The backdrop is formed by a skyline of Clearwater's buildings under a bright blue sky, framed by lush tropical vegetation.

Home in Clearwater Beach

Waterfront 4BR | Walk to Beach | Pool & Spa

This stunning 3 story 4BR/3BA townhome (built in 2017) blends luxury, comfort, & the perfect beach town vibe. 2 blocks from the world famous white sands of Clearwater Beach and directly on the intracoastal waterway, this home offers everything you need for an unforgettable Florida getaway. Pool and hot tub access! Ideal for families, couples, or groups of up to 10 guests looking for a premium vacation experience. Beaches, boating, biking, shops, food, drink & water fun all steps away!

FamilyKitchenWifi

4.98 out of 5 average rating, 237 reviews

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

KitchenFamilyDecor

Townhouse in Clearwater Beach

The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.

3 Bedroom Waterfront Paradise Sleeps 8

Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

Indoor spacesFamilyLocation

4.99 out of 5 average rating, 148 reviews

Popular amenities for Clearwater Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Apartment in Indian Shores

Panoramic Gulf View Beachfront Condo

Indoor spacesFamilyComfort

4.93 out of 5 average rating, 153 reviews

A scenic view of the Intra-Coastal Waterway features several boats docked along wooden piers, framed by palm trees. The clear blue water reflects the sky, while distant buildings line the shore, creating a tranquil coastal setting.

4.86 out of 5 average rating, 311 reviews

Sandy Feet Retreat

KitchenIndoor spacesNearby

4.9 out of 5 average rating, 187 reviews

Heated Pool & Spa • Pergola Swing

FamilyKitchenGetting around

Townhouse in Clearwater Beach

The exterior of the multi-story vacation home is shown, featuring light-colored walls with arched windows and balconies. Palm trees line the front, and a paved driveway leads to individual garages below. The rooftop terrace is visible, suggesting additional outdoor space and amenities.

Luxurious Beach House, Private Rootop, & Hot Tub!

KitchenFamilyNearby

4.86 out of 5 average rating, 180 reviews

A cozy sitting area is featured on the private balcony, highlighted by a circular rattan chair adorned with soft cushions. Green plants provide a touch of nature, while water views and boats can be seen beyond the railing, enhancing the relaxing atmosphere.

4.99 out of 5 average rating, 147 reviews

Waterfront Condo | Steps to Clearwater Beach 2King

Indoor spacesKitchenAccess

Superhost

4.81 out of 5 average rating, 171 reviews

Hot Tub, Heated Pool, Mini Golf | Island Vibes

FamilyIndoor spacesGetting around

4.97 out of 5 average rating, 257 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

Indoor spacesFamilyBack garden

4.88 out of 5 average rating, 147 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

KitchenFamilyParking

Family- and pet-friendly home rentals

Apartment in Belleair Beach

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

FamilyIndoor spacesBeach

4.72 out of 5 average rating, 548 reviews

A spacious outdoor terrace features modern seating arrangements with gray cushions and white wooden frames. Clear glass railings provide unobstructed views of the Gulf of Mexico, while a single palm tree adds a touch of greenery to the coastal setting.

4.84 out of 5 average rating, 192 reviews

Beachfront on Clearwater Beach!

FamilyIndoor spacesBathroom

Superhost

A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.

Cottage in Clearwater Beach

Mermaid Cottage

Indoor spacesKitchenDecor

4.84 out of 5 average rating, 170 reviews

A serene outdoor space features a heated saltwater pool with gentle lighting, surrounded by a screened enclosure. Comfortable seating areas are arranged nearby, with a covered space for relaxation and an outdoor bar in the background, creating an inviting atmosphere for leisure and gatherings.

4.91 out of 5 average rating, 133 reviews

Luxury Oasis • Heated Salt Pool • Near Beaches

KitchenFamilyBathroom

An inviting outdoor space features a heated pool and a shaded area adorned with cafe lights. Two hanging egg chairs and comfortable seating arrangements complement the modern wooden furniture. The stylish striped rug enhances the atmosphere, while the pool's tranquil blue water is visible in the background.

4.95 out of 5 average rating, 164 reviews

Palm Paradise - Family Amenities+Central Location

FamilyKitchenSleep quality

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Your private Waterfront Pool home!

FamilyKitchenBack garden

4.97 out of 5 average rating, 234 reviews

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 346 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

KitchenFamilyAccess

A heated pool area is surrounded by tropical plants and palm trees. A tiki hut provides shaded seating, and lounging chairs are positioned around the pool. A textured stone deck complements the inviting water of the pool, creating a relaxed atmosphere for guests.

4.9 out of 5 average rating, 129 reviews

Tiki House •Sleeps 10 •Walk to Beach + Heated Pool

FamilyIndoor spacesCleanliness

Family-friendly home rentals with a pool

Apartment in Indian Rocks Beach

The image captures a view of the Splash Harbour Water Park and adjacent condo building. Bright colors of the water slides contrast with the greenery of palm trees. The inviting pool area is visible, surrounded by lounge chairs and scenic pathways.

Waterfront, Harbourside, Water Park, Beach, #6620

KitchenIndoor spacesBathroom

4.87 out of 5 average rating, 263 reviews

4.99 out of 5 average rating, 133 reviews

Villa in Palm Harbor

Palm Haus • Heated Pool • Near Beach • Game Room

Indoor spacesKitchenLong stay

A spacious outdoor area features a heated pool surrounded by a screened enclosure. Two lounge chairs are positioned beside the pool, and a barbecue grill is visible near the edge, providing an ideal setting for relaxation and meals.

4.85 out of 5 average rating, 141 reviews

Heated Pool Home | Close to Clearwater Beach

KitchenFamilyLocation

Bungalow in Indian Rocks Beach

A pool area is surrounded by vibrant tropical landscaping, featuring lounge chairs arranged around a circular pool. Soft lighting illuminates the scene, enhancing the greenery. In the background, a pink float adds a playful touch to the inviting ambiance of the outdoor space.

Neptune's Nest | Amazing Htd Pool | Steps to Beach

Indoor spacesFamilyGetting around

4.93 out of 5 average rating, 178 reviews

4.97 out of 5 average rating, 155 reviews

Apartment in Clearwater

Spacious Key West Retreat, Fun 2 BR, Resort Pool

FamilyIndoor spacesLayout

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

4.97 out of 5 average rating, 180 reviews

Palm Oasis | Heated Pool | Near Beaches

KitchenIndoor spacesSleep quality

4.95 out of 5 average rating, 73 reviews

Heated pool, pickleball, mini golf near beaches

Indoor spacesKitchenNearby