Family-friendly holiday rentals in Sand Key

4.98 out of 5 average rating, 140 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

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.

4.93 out of 5 average rating, 167 reviews

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

An original early 1900 Indian Rocks Beach bungalow, updated with all the comforts of home. Grill on your private patio or relax in the pool area in our tropically landscaped grounds. Cross Gulf Boulevard to 8th Ave beach access to the beautiful turquoise waters and white sandy beaches of the Gulf of Mexico. Enjoy swimming, shelling and fishing as you live the island life. Splash Harbour water park, shops and restaurants are within walking distance. Come for an unforgettable stay! City tax#1479

5 out of 5 average rating, 158 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 saltwater pool & playground

★ 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

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, 124 reviews

Heated Pool and Spa | 5 min to beach

Welcome to our home in Largo, Florida. This is a modern and comfortable place with a heated pool and spa, just minutes from Clearwater and Indian Rocks beaches. The kitchen has everything you need, and the living spaces are meant for relaxed stays with family or friends. The house has 3 bedrooms and 2 bathrooms and sleeps up to 6 guests comfortably. Whether you spend the day at the beach or by the pool, you’ll have an easy place to unwind and enjoy your time here. We hope you feel at home.

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.

4.72 out of 5 average rating, 524 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

No impact from hurricanes! - RECENTLY RENOVATED. This cozy 1 bedroom condo with a kitchen in Belleair Beach just steps from the sugar-white sand and crystal clear waters that are consistently ranked among America's most beautiful beaches! It has a lovely pool area that overlooks the gulf with a patio, chairs and grills. You’ll love the beachfront views and quiet ambiance. 3rd Floor, balcony with DIRECT BEACH/GULF VIEW. Minutes away from Clearwater Beach. Perfect for couples! ONE parking spot.

Superhost

The outdoor pool, surrounded by palm trees, reflects the clear blue sky. Comfortable loungers are placed nearby, offering ample space for relaxation. The glistening water leads to views of the waterfront, enhancing the serene atmosphere of the outdoor environment.

4.83 out of 5 average rating, 366 reviews

Stunning views! Spot dolphins from the pool!

BTR#2114 This home has it ALL including incredible open water sunsets! Every detail has been carefully thought out and updated. This is a VERY upscale, coastal, single story waterfront home. A complete waterfront remodel w/ dock & pool that looks and feels like a new home w/ stunning water views from your own back patio! The water glistens and sparkles from 3 pm thru sunset and after, the sky is set on fire for 40 minutes. White sandy beach is only few blocks away! Amazing home inside & out!

4.98 out of 5 average rating, 166 reviews

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

Villa in Largo

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Flat in Indian Rocks Beach

The inviting pool area is surrounded by palm trees and features a vibrant pink flamingo float. Comfortable chaise loungers line the pool deck, offering relaxation options. A wooden fence provides privacy, and the outdoor space is designed for leisure and enjoyment.

4.96 out of 5 average rating, 150 reviews

Blushing Flamingo | Pool | Bikes | Steps to Beach

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared pool with sunshelf and chaise loungers ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills

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, 136 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.

4.99 out of 5 average rating, 267 reviews

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Flat in Dunedin

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

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.

4.96 out of 5 average rating, 217 reviews

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

Villa in Indian Rocks Beach

4.9 out of 5 average rating, 108 reviews

Waterfront saltwater Pool home w boat slip

2 King Beds 1 bath Vintage cottage w outdoor saltwater pool on intracoastal waterway. Perfect for 1-4 guests. Bring your small boat no charge. ( Must provide your own supplies/ ties/ bumpers) Great for water sports, fishing, nature lovers. Only quiet respectful guests welcome. Work from home office with a beautiful view. This is someone's private home half of the year. It's professionally cleaned, welcoming, down to earth. BTR1587

Popular amenities for Sand Key family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A four-person outdoor dining table is set with plates and glasses of red wine, overlooking the waterway. A double kayak is visible on the shore, and boats are docked in the background under a blue sky with a few clouds.

4.92 out of 5 average rating, 75 reviews

Waterfront | King Bds | Htd Pool | BBQ | 2 Kayaks

4.94 out of 5 average rating, 124 reviews

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

Home in Tampa

The Jungalow SOHO - Pool/Hot Tub

4.96 out of 5 average rating, 161 reviews

[Kids Favourite] Family Fun Getaway | Heated Pool

4.97 out of 5 average rating, 250 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

4.99 out of 5 average rating, 193 reviews

Piece of paradise in Indian Rocks Beach.

An inviting outdoor space features a heated saltwater pool and spa surrounded by sun loungers. A dining area is visible next to the pool, with a backdrop of palm trees and a screened lanai. The bright sky enhances the relaxing atmosphere.

5 out of 5 average rating, 98 reviews

Sandy Morning Restored | Pool Spa

4.99 out of 5 average rating, 111 reviews

Best Celebration - Heated Pool - Hot Tub - Arcade

4.99 out of 5 average rating, 137 reviews

[Kids Favourite] Family Fun Retreat | Heated Pool

Family- and pet-friendly home rentals

An outdoor space is depicted, featuring a heated pool surrounded by lounge chairs. A dining area with a table and chairs sits beneath an umbrella, while a mini golf setup and cornhole boards are visible. The scene is illuminated by warm sunset tones.

4.88 out of 5 average rating, 130 reviews

Clearwater Playhouse! Heated Pool, Mini Golf

An outdoor seating area is illuminated by string lights, featuring a table with a fire pit at its center. Two wine glasses filled with red wine are positioned next to a bottle of wine. Nearby, two red cups and several beer bottles add to the relaxed atmosphere.

4.96 out of 5 average rating, 181 reviews

Cozy Stylish Home w/ Heated Pool & Big Parking

5 out of 5 average rating, 209 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

4.96 out of 5 average rating, 132 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

A private backyard features a heated pool surrounded by a spacious patio area. A shaded dining space and lounge chairs are visible alongside the pool. Lush greenery and palm trees provide a natural setting, while a fire pit seating area is positioned on the lawn.

4.96 out of 5 average rating, 101 reviews

Heated Pool-1.5 mile to Beach- 3 Bikes-OutsideTV

The exterior of a single-story home is presented, featuring a light-colored brick facade and a concrete driveway. Lush green grass surrounds the property, and young trees are planted in the front yard. A garage is visible on the left side, with a welcoming blue front door.

4.93 out of 5 average rating, 123 reviews

Mac Crillus Beach House Pet friendly

4.97 out of 5 average rating, 372 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

Apartment in Indian Rocks Beach

4.86 out of 5 average rating, 107 reviews

Walk to Beach, Bars, and Restaurants Nearby

Family-friendly home rentals with a pool

5 out of 5 average rating, 28 reviews

A private heated pool features a connected spa area, both surrounded by a paved patio with comfortable seating. A waterfall element adds a tranquil touch, while the screened enclosure allows for sun and fresh air in the inviting outdoor space.

Home in Safety Harbor

Lazy Lizard Villa! With Heated Pool/Spa/ Waterfall

The outdoor area features a heated saltwater pool illuminated with a soothing blue hue. Surrounding palm trees and tropical landscaping enhance the tranquil atmosphere. A yellow and white striped umbrella provides shade beside the pool, offering a picturesque view of the waterway beyond.

4.91 out of 5 average rating, 97 reviews

OceanView~Golf Cart~Heated Pool~5k SqFt~Game Room

Superhost

4.9 out of 5 average rating, 31 reviews

Water Lover's Paradise | Waterfront • Dock • Pool

The outdoor space features a heated pool surrounded by a tiled patio. Three lounge chairs offer a place to relax under a large umbrella. A whimsical pool float adds a playful touch. A colorful mural of tropical leaves is visible on the exterior wall.

4.98 out of 5 average rating, 41 reviews

Muse by the Shore

Apartment in Clearwater Beach

A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.

4.99 out of 5 average rating, 186 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

A circular arrangement of six turquoise Adirondack chairs surrounds a central fire pit, which is built from stone. The area is laid out with white gravel and bordered by lush greenery, including palm trees, offering a cozy setting for outdoor gatherings.

5 out of 5 average rating, 49 reviews

Largo Palms Duplex-2BR/2BA + Heated POOL Unit A

A modern building with a mix of light-colored stucco and wood paneling is shown. The three-level structure features multiple balconies and large windows. A landscaped front yard includes palm trees, and a driveway accommodates a parked black vehicle.

4.94 out of 5 average rating, 36 reviews

The Sunshine House!