Family-friendly holiday rentals in Clearwater

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 302 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

FamilyKitchenPets

5.0 out of 5 average rating, 170 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

FamilyIndoor spacesHeating

4.99 out of 5 average rating, 127 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

FamilyIndoor spacesLaundry

4.91 out of 5 average rating, 196 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

KitchenIndoor spacesLaundry

5.0 out of 5 average rating, 116 reviews

Dream Retro | Near Beaches | Pets Welcome-fenced!

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.

KitchenIndoor spacesSleep quality

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, 179 reviews

Palm Oasis | Heated Pool | Near Beaches

Have fun with the family or just a friend getaway at this stylish cozy POOL home. This newly remodeled 3-bedroom 2-bath home, centrally located between Clearwater and St. Petersburg and a 30 min drive to Tampa to visit all the local attractions. Very close to plenty of restaurants, shopping, and Beaches. This home has everything needed from quality mattresses to kitchen essentials and “Smart TV’s” in every room, very close to shopping, restaurants, movies, Walmart, etc. “Must be 21 to book”.

Indoor spacesKitchenNearby

Condo in Clearwater Beach

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, 180 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.

Indoor spacesFamilyAccess

The private backyard features a screened-in heated pool, surrounded by lounge chairs for relaxation. A portable grill is positioned nearby, and colorful pool floats are present in the water. The evening sky showcases soft hues of pink and purple, enhancing the serene atmosphere.

5.0 out of 5 average rating, 102 reviews

Heated pool 12 min to beach w/ Gameroom, king beds

Welcome to Coastal Sanctuary! Comes stay at our modern, 4 bedroom heated saltwater pool home in a family friendly neighborhood that features an open floor plan, oversized kitchen & amenities to provide you, your family & friends with everything you need to enjoy a true Florida vacation experience including a heated pool, game room & more! 12 min – Clearwater Beach 15 min – St. Pete-Clearwater International Airport 25 min – Tampa International Airport 35 min – Downtown Tampa 90 min – Disney

KitchenIndoor spacesBeach

An air-conditioned indoor golf simulator features a vibrant neon golf graphic in the background. A person is positioned on a putting green, preparing to putt a golf ball towards a screen displaying a course. Equipment and seating are arranged thoughtfully around the space.

4.82 out of 5 average rating, 138 reviews

Golf Sim, Heated Pool, Games | Clearwater Dream!

Clearwater luxury! Not only is this 4 bedroom home just 10 minutes away from some of the most beautiful beaches you'll ever see, it's also LOADED with fun and games! A luxury backyard with a heated pool, indoor golf simulator, pool table, mini golf, and much more! Enjoy your dream family vacation here today! 5 min - Downtown Largo 10 min - Clearwater Beach 15 min - Sand Key Park, Ruth Eckerd Hall, Clearwater Int. Airport 30 min - Tampa Experience Clearwater With Us & Learn More Below!

KitchenIndoor spacesLocation

4.94 out of 5 average rating, 114 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

FamilyKitchenHospitality

4.98 out of 5 average rating, 231 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

KitchenFamilyBarbecue

4.94 out of 5 average rating, 99 reviews

Just Wow! Luxury & Huge Heated Pool & Spa Home!

🏠 Immerse yourself in a world of 5 ⭐⭐⭐⭐⭐ service and accommodations! Welcome to your dream getaway in Clearwater! Dive into luxury at this beautifully renovated 5-bedroom, 3-bathroom home with not one, but two inviting living spaces. Step outside onto the expansive covered lanai overlooking a pristine, sparkling saltwater pool and spa. Privacy is paramount in the fully fenced yard, making it your own secluded oasis. Professionally Managed by ❤️ Emperor Rentals 👑

FamilyKitchenView

Popular amenities for Clearwater family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.89 out of 5 average rating, 172 reviews

Walk to BayCare Ballpark! Pool, Hot Tub, Pets OK

FamilyIndoor spacesComfort

4.95 out of 5 average rating, 174 reviews

10 Min to Beach | Heated Pool, Hot Tub, Arcades

Indoor spacesKitchenBeach

4.97 out of 5 average rating, 152 reviews

Clearwater Gem! XL-Pool | Courts & More.

KitchenFamilyBackyard

4.95 out of 5 average rating, 199 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

Indoor spacesFamilyQuiet

A modern kitchen is presented with navy blue cabinetry and a spacious island featuring seating for four. Quartz countertops and stylish light fixtures add elegance. Natural light streams through a nearby window, illuminating the adjacent dining area with a table and chairs.

4.88 out of 5 average rating, 144 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

KitchenIndoor spacesLaundry

4.78 out of 5 average rating, 112 reviews

Lovely Home with Heated Pool/Hot Tub/Playground

Indoor spacesFamilyBackyard

4.83 out of 5 average rating, 131 reviews

A spacious pool area features a heated saltwater pool and a hot tub surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a grill is visible, providing an inviting outdoor space. The screened enclosure offers a sense of privacy and comfort.

Home in Belleair Bluffs

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

KitchenIndoor spacesValue

An inviting pool area features a clear blue pool alongside a spacious hot tub, both surrounded by a grey stone deck. Comfortable loungers are arranged under an umbrella, offering shade. Sunlight filters through the screened enclosure, creating a bright and open atmosphere.

4.92 out of 5 average rating, 131 reviews

Heated Pool and Spa | 5 min to beach

FamilyIndoor spacesAccuracy

Family- and pet-friendly home rentals

Superhost

A fenced-in pool is featured, showcasing a clear blue water surface. Bright green floats rest on the water. Two teal Adirondack chairs are positioned beside the pool, creating an inviting leisure area. Sunlight brightens the scene, surrounded by decorative landscaping.

4.92 out of 5 average rating, 135 reviews

Sleeps 9 | Pool + Game Room Near Beach

Indoor spacesKitchenCondition

4.95 out of 5 average rating, 147 reviews

Artsy oasis in Clearwater

FamilyIndoor spacesBathroom

The outdoor area presents a heated swimming pool surrounded by a patio made of stone. Lush greenery and tropical plants frame the pool, while a nearby gazebo offers shaded seating. Bright blue lounge chairs are positioned by the water, creating a relaxing environment.

4.98 out of 5 average rating, 120 reviews

Paradise palms oasis Clearwater

Indoor spacesKitchenSleep quality

4.94 out of 5 average rating, 108 reviews

Star House! Heated&Salt pool/ Clearwater Beach

Indoor spacesKitchenOutdoor spaces

A shaded outdoor space features two hanging egg chairs and a wooden coffee table, surrounded by a striped rug. A comfortable seating area with a love seat and additional chairs faces the pool, while large glass doors provide access to the interior.

4.95 out of 5 average rating, 161 reviews

Palm Paradise - Family Amenities+Central Location

FamilyIndoor spacesAccess

4.92 out of 5 average rating, 164 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

KitchenIndoor spacesHospitality

Condo in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 478 reviews

Amazing views on beachfront

FamilyKitchenAir conditioning

4.94 out of 5 average rating, 291 reviews

Family/Group Getaway w/ Pool Near Clearwater Beach

FamilyKitchenTV

Family-friendly home rentals with a pool

A spacious living area features a large, curved sectional sofa adorned with decorative cushions. A circular coffee table rests on a soft area rug, while a television is mounted on a light-colored wall. Natural light enters through multiple windows, enhancing the bright space.

4.89 out of 5 average rating, 144 reviews

Heated Saltwater Pool Home 3 Miles to Beach

FamilyIndoor spacesDecor

4.98 out of 5 average rating, 128 reviews

A spacious backyard is featured, showcasing a heated saltwater pool surrounded by a large paver deck. Lush green grass fills the area, bordered by well-maintained landscaping. Tall trees provide shade in the background, contributing to the serene outdoor environment.

Home in Seminole

JOJO'S Beachside 1Acre Estate-New Pool

KitchenFamilyCheck-in

4.88 out of 5 average rating, 145 reviews

3 BR/2B pool home WiFI and Brand new furnishings

Indoor spacesFamilyHeating

4.94 out of 5 average rating, 69 reviews

Clearwater Heated Pool Family-Friendly. Near Beach

Indoor spacesFamilyPool

Home in Indian Rocks Beach

5.0 out of 5 average rating, 9 reviews

Harbor Villa | Waterfront Pool & Spa | Firepit

Indoor spacesComfortQuiet

Home in Indian Rocks Beach

5.0 out of 5 average rating, 5 reviews

Bay Oasis intercoastal pool home w/ hot tub

FamilyViewHospitality

4.96 out of 5 average rating, 54 reviews

Private Pool Oasis | 4BR • Game Room • Mini Golf

Indoor spacesFamilyPool

An inviting private pool reflects the sunlight beneath a screened enclosure, surrounded by lush greenery. A foosball table in a bright indoor space offers entertainment, while a charming dining area features wicker chairs and tasteful decor. A well-equipped kitchen area showcases jars and appliances.