Family-friendly holiday rentals in Clearwater Beach

4.98 out of 5 average rating, 101 reviews

Lovely Condo minutes from beach & King bed

Kick back and relax in this calm, stylish space.Minutes away from Clearwater Famous Beach.You will be pleased with high ceilings and open floor plan.King size bed in the Bedroom with balcony and 55" smart Tv. Walk-in closet and updated bathroom. Spacious covered patio style balcony. Full-size washer and dryer inside the unit. Fully updated and equipped kitchen. Specious living room with a sleeper sofa that can sleep two quests and 65"smart Tv. Heated outdoor pool, gym, fast wifi internet, cable

Apartment in Treasure Island

An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.

4.98 out of 5 average rating, 150 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and heated pool. Visit nearby restaurants, John's Pass Boardwalk and live music.

4.93 out of 5 average rating, 173 reviews

The outdoor area showcases a saltwater pool within a screened lanai, surrounded by a patio area with seating. The pool area is illuminated by natural light, enhancing the space's openness. A game room features plush seating arranged for viewing films, with walls designed for a cinematic experience.

Home in Clearwater

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

4.97 out of 5 average rating, 137 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents 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.

Apartment in Indian Rocks Beach

An inviting living area showcases a comfortable blue couch with a colorful throw blanket. A wooden dining table is positioned nearby, and natural light flows through expansive glass doors leading to a balcony with a glimpse of trees and water outside.

4.96 out of 5 average rating, 102 reviews

Beachside, Lux, 3 Minute Walk, Views Fam.-Friendly

Completely remodeled luxury beachside condo with balcony. Water/beach view- balcony and living room. Short walk down to beach. Saatva Luxury mattress in Master. 2nd Bed- has double over double bunk bed with twin trundle. Couch -pullout bed that sleeps two more. Kid-friendly! Pack n play with memory foam mattress and diaper genie. Toys, child-proofing, kid utensils etc in unit. Beach supplies, towels, wagon, chairs, toys umbrellas.. below in storage. Paddleboard and bike rental available nearby!

4.96 out of 5 average rating, 264 reviews

Guest suite in Tampa

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”

Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

4.93 out of 5 average rating, 146 reviews

An open living area features a blue couch and two bar stools at a kitchen counter. A green bed is visible in the background, with a light-colored dresser against the wall. Soft lighting brightens the space, which has light blue walls and patterned flooring.

Flat in Clearwater Beach

NEW! High End King Mattress! 10 Steps to the beach

AMAZING LOCATION! Located within crawling distance of the sugary white sands of the world famous Clearwater Beach! Equipped with a Premium King Casper Wave Hybrid Snow Mattress which retails at $4,000, to ensure an amazing nights sleep. Located in a small building with just 6 units, only 1 house from the beach. Walking distance to practically everything in town including many great restaurants, bars, shops, Pier 60, the marina & more, yet still located on a quiet street. No car is necessary!

4.96 out of 5 average rating, 113 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.

Home in Clearwater

Luxury Oasis • Heated Salt Pool • Near Beaches

Welcome to Paradise Palms 🌴☀️- your tropical, family-friendly getaway w/ a private heated saltwater pool! Newly renovated & cleaner than a hotel, the home is filled w/ luxury amenities to create a truly unforgettable family vacation. With 7 comfy beds, there's plenty of room for everyone. Just 14 min to the famous Clearwater Beach & other beautiful white sand beaches! It's finally time to relax & soak up some Florida sun! Come experience all that Paradise Palms & Clearwater have to offer.

Apartment in Indian Shores

4.9 out of 5 average rating, 166 reviews

Gulf Side Florida Charm 1/1 Condo 60 Steps To Sand

Step back in time at Postcard Paradise, a charming beachside cottage that captures the magic of Old Florida. Nestled just steps from the shore, our eclectic retreat feels like living inside a vintage postcard. Sun-faded colors, and tropical murals set a nostalgic mood, while modern comforts keep things easy and relaxed. Each cozy room is filled with hand-picked decorations, breezy linens, and quirky coastal finds, creating a one-of-a-kind space where every corner tells a story.

Flat in Indian Rocks Beach

The vibrant living area features bold red seating and a colorful wall adorned with tropical patterns. A soft white trundle bed is visible, surrounded by natural light from the windows. A dining space is highlighted with a circular table, bright dishes, and decor reflecting a cheerful atmosphere.

4.94 out of 5 average rating, 101 reviews

South Beach Retreat, Steps from the Beach!

🏝️ Discover a Tropical Paradise in Indian Rocks Beach! 🌊 Escape to a coastal oasis where sun-soaked beaches and swaying palm trees beckon you! Welcome to our exquisite apartment unit, exuding the charm of a delightful tropical retreat. 🛏️ Bedroom Bliss: Unwind in the luxurious 1-bedroom oasis, featuring a lavish King size bed. 🛀🏻 Bathroom: Complete with a toilet, tub, and shower. 🌈 Vibrant Living Space: Kick back and relax in the vibrant and color-themed living area.

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.

4.99 out of 5 average rating, 125 reviews

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.

A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.

4.99 out of 5 average rating, 148 reviews

Ocean Breeze • Easy - Heated Pool Access

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

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 Madeira Beach

4.95 out of 5 average rating, 154 reviews

COASTAL CHIC! Luxury Apartment with Oceanviews

Cottage in Clearwater Beach

4.75 out of 5 average rating, 233 reviews

Lemon Cottage Steps from Beach

4.91 out of 5 average rating, 119 reviews

Home in Clearwater

Clearwater Retreat: Heated Pool, Spa & Pet-Friendl

Apartment in St. Pete Beach

4.93 out of 5 average rating, 221 reviews

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo

Apartment in Indian Shores

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

4.94 out of 5 average rating, 133 reviews

Tropical Beachfront Penthouse-Beach Cottages

Apartment in Indian Rocks Beach

A spacious living room features a large sectional sofa adorned with decorative cushions, providing a comfortable seating area. A coffee table with a natural wood finish is central to the room. Sliding glass doors open to a balcony, revealing views of the beach and ocean.

5 out of 5 average rating, 105 reviews

Beach Days & Family Fun - Last Minute Openings

4.98 out of 5 average rating, 124 reviews

Home in Largo

[Kids Favourite] Family Fun Retreat | Heated Pool

4.94 out of 5 average rating, 127 reviews

Flat in St. Petersburg

Waterfront studio! Heated pool and hottub

Family- and pet-friendly home rentals

Bungalow in Indian Shores

An aerial view showcases a cluster of charming two-story homes nestled near the beach. The golden hues of the sunset reflect off the water, while the sandy shore and gentle waves create a serene coastal atmosphere.

5 out of 5 average rating, 228 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Cottage in Indian Rocks Beach

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

4.99 out of 5 average rating, 204 reviews

Luxury Beach Cottage | Walk to Dining & Sunset

4.89 out of 5 average rating, 106 reviews

A spacious living area showcases a dark gray sleeper couch adorned with decorative pillows, including one that reads 'Beach Life.' A light-colored wall provides a backdrop for a decorative sign that reads 'happy place.' Natural light filters in from windows leading to the kitchen.

Home in Clearwater Beach

Beachfront Getaway with Patio – Perfect For 6

Guest house in Clearwater

A light green room features a queen-size bed with a white quilt and decorative pillows. A small dining area with a round table and two chairs is visible alongside a neutral-toned sofa. Large windows provide natural light, and indoor plants are seen through the glass doors.

4.89 out of 5 average rating, 238 reviews

Cottage on Pinellas Bike Trail

4.96 out of 5 average rating, 183 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

Superhost

Flat in Clearwater

4.89 out of 5 average rating, 194 reviews

*Special Pricing* Studio Apt, 3 mi from beach

4.98 out of 5 average rating, 363 reviews

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

Walk Downtown and to Waterfront, Mins to Beaches

4.95 out of 5 average rating, 112 reviews

A spacious bedroom features a plush king bed with a light-colored blanket and two dark nightstands on either side. Vertical windows offer natural light, while neutral gray walls and wood flooring create a calm atmosphere.

Flat in Clearwater

Relaxing beach gateway

Family-friendly home rentals with a pool

A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.

5 out of 5 average rating, 56 reviews

Wonderful Condo at Avalon - Fully Renovated!

Apartment in Indian Rocks Beach

A spacious balcony is bordered by tall palm trees, offering a view of the calm Gulf of Mexico and white sand beach. The clear blue sky complements the serene ocean, creating a tranquil setting for relaxation.

4.89 out of 5 average rating, 103 reviews

Gulf-View 2BR/2BA Beach Condo!

Apartment in Indian Shores

A waterfront view showcases the community pier lined with palm trees, providing access to the Intracoastal waterway. The nearby building features balconies and patio furniture under blue umbrellas, enhancing the leisure atmosphere. Multiple docks extend into the clear water, inviting relaxation.

4.97 out of 5 average rating, 113 reviews

Blue Sea Renity -Steps to Beach| Heated Pool

4.9 out of 5 average rating, 224 reviews

A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.

Apartment in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.

4.96 out of 5 average rating, 136 reviews

Bright and Spacious 1Bed/1Bath condo.

Bungalow in Indian Rocks Beach

A private tiki hut features a thatched roof, ambient lighting, and a large television. Seating is provided by several lounge chairs and a unique wicker chair, arranged around a stone floor. Lush greenery surrounds the area, enhancing the outdoor experience.

4.89 out of 5 average rating, 148 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

4.91 out of 5 average rating, 412 reviews

A spacious outdoor entertainment area features a tropical saltwater pool surrounded by a screened enclosure. Colorful loungers in vibrant pink and green are positioned near the pool, complemented by a dining table. A shaded area offers comfort for relaxing in the sun.

Home in St. Petersburg

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!