Family-friendly vacation rentals in Sand Key

5 out of 5 average rating, 126 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 & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

4.97 out of 5 average rating, 133 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

A roadside view of a pink cottage features large windows inviting natural light. A white door is visible, with two chairs placed on the gravel-covered area. Surrounding greenery enhances the outdoor space, while a parking lot provides convenient access.

4.94 out of 5 average rating, 198 reviews

Vintage Florida Beach Efficiency

Just a short walk to the beach, this a great beach getaway for couples or families with one child. On your way stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2024, this unit is updated, very clean & worry free. This cottage is located in a quiet residential neighborhood and a great place to relax. Laundry on shared screened porch. Dogs allowed ($35 extra) add them on # of guests page . Easy refund policy. Level 2 EV charger

4.91 out of 5 average rating, 323 reviews

A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.

Guest suite in Largo

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

4.96 out of 5 average rating, 143 reviews

A spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.

Place to stay in Dunedin

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

4.83 out of 5 average rating, 280 reviews

Apartment in Largo

Cozy Largo Studio

Fantastic studio consisting of a comfortable queen bed, and small kitchenette, perfect for a long term stay or weekend get away. Parking on premises. Unit was newly renovated and is impeccably kept. Minutes away from popular Indian Rocks beach / Belleair beach and clear water beach. Easy hassle free check in. (This is a one room studio with 1 queen bed as shown) this is a private apartment with its own front door. Not a shared space. Close to the Largo hospital, medical students welcome

4.95 out of 5 average rating, 100 reviews

Apartment in Largo

Hidden Oasis #3, *construction discount!*

*Construction discount! The yards and upstairs apartment are undergoing renovations. Please note the seating on the decks is limited and there may be noise in this unit during the day from the work above.* Walk into this welcoming apartment and find your paradise! This cozy space has shared access to a large courtyard w/ grill & smoker. Short 10-minute drive to the best free parking along the Gulf beaches (Indian Rocks Beach). Free bikes! Come make yourself at home in this Hidden Oasis 🌴

4.94 out of 5 average rating, 120 reviews

A bright and airy living room features a large, blue sectional couch adorned with decorative pillows. A flat-screen TV is mounted on a stone accent wall, while natural light filters in through sheer white curtains. A wooden coffee table displays a small decorative tray.

Home in Clearwater

Best Location in Clw! Near Beach & Saltwater Pool!

PRIME LOCATION NEAR BEACH! Welcome to our newly renovated vacation home in beautiful Clearwater, FL. Located in the heart of downtown Clearwater within walking distance to several restaurants and shops and just a few mins drive to Clearwater Beach. This coastal styled home comes with a heated pool (at no extra charge), putting green, and a fun little game room for kids! The entire home is yours to enjoy and comes fully stocked with everything you need for a relaxing beach getaway vacation.

Apartment in Clearwater Beach

4.75 out of 5 average rating, 100 reviews

Fresh for 2025: Retro Beach Oasis with Color Pop

Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in -Pet friendly (One Pet max -$150 fee) We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

Apartment in Indian Rocks Beach

The shared resort-style backyard features a large heated pool surrounded by lounge chairs and umbrellas. Lush palm trees provide shade, and a peaceful ambiance is created by the surrounding greenery. The inviting blue sky completes this outdoor relaxation area.

4.94 out of 5 average rating, 140 reviews

New! Starfish Wishes! Heated Pool! Steps to beach!

COMPLETELY REMODELLED beachy 2 bedroom vacation rental! Located a very short one block walk down a palm tree lined path to the sugary sands of Indian Rocks Beach and across the street from a beautiful park! Out back, you will find a large HEATED pool (Currently 90°!) with plenty of lounge chairs, dining tables, a new Weber BBQ grill, fire pit, pool floats & more. To make your trip as easy as possible, we provide you with all your beach needs, towels, umbrella, beach chairs & more.

4.97 out of 5 average rating, 145 reviews

A guest house with bright yellow siding is set against a backdrop of lush trees. The entrance features a dark door and a small patio area with seating. Surrounding greenery adds a touch of nature, complemented by a white fence providing privacy.

Guesthouse in Clearwater

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

Apartment in Indian Rocks Beach

A heated pool is surrounded by palm trees, with two blue sunshelf loungers partially submerged in the water. Spacious chaise loungers are positioned around the pool area, featuring a light-colored stone deck and privacy provided by a wooden fence in the background.

4.97 out of 5 average rating, 147 reviews

Triplex- walk to beach, heated pool, bikes

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ 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 ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

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

Guest suite in Clearwater

4.76 out of 5 average rating, 139 reviews

La Casita, 1 of 3 rentals on-site/pool/near beach

A private outdoor pool is surrounded by a spacious patio, featuring tropical landscaping and palm trees. The pool area includes a shallow ledge for lounging. The exterior of the home, with light-colored stucco, is visible in the background alongside a securely fenced yard.

4.86 out of 5 average rating, 173 reviews

The Paradise Cove No. 1

4.96 out of 5 average rating, 190 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

4.9 out of 5 average rating, 113 reviews

A view of a heated saltwater pool is framed by two lounge chairs, positioned on a grassy area. Red umbrellas provide shade for seating areas, and a spacious patio can be seen in the background, featuring modern outdoor furniture and a neutral-colored house.

Home in Clearwater

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

4.97 out of 5 average rating, 241 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

Home in Indian Rocks Beach

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.

5 out of 5 average rating, 178 reviews

Piece of paradise in Indian Rocks Beach.

4.94 out of 5 average rating, 111 reviews

The setting sun casts a warm glow over the beach, reflecting off the calm water. Silhouettes of individuals can be seen walking along the shore, while gentle waves lap at their feet. The sky features soft pastel colors, enhancing the tranquil atmosphere.

Condo in Indian Shores

Bay Shores Yacht & Tennis Club Indian Shores FL

4.86 out of 5 average rating, 491 reviews

A spacious balcony offers water views featuring palm trees and lounge furniture. The exterior of the building showcases a light-colored facade. A living area is furnished with a soft couch and a dining set, bathed in natural light from large windows. A pool area is visible with lounge chairs and palm trees lining the water's edge.

Condo in St. Petersburg

Waterfront condo on top floor @ Boca Ciega Resort

Family- and pet-friendly home rentals

Guesthouse in Town 'n' Country

4.99 out of 5 average rating, 267 reviews

Entire Guest House near Tampa airport

4.94 out of 5 average rating, 221 reviews

A colorful exterior is framed by lush greenery and tropical plants. A brick pathway leads to the entrance, with a dining area featuring a table and chairs amidst the vibrant surroundings. Sunlight streams through the trees, creating a serene atmosphere.

Apartment in Dunedin

The Coastal Retreat

4.92 out of 5 average rating, 117 reviews

A cozy living area showcases a dark sectional couch complemented by a decorative wall featuring framed artwork. A round mirror reflects light, while a nearby table with a geometric lamp adds warm illumination. Soft textures are provided by the area rug beneath.

Home in Seminole

Suite w/ Private Entrance

4.91 out of 5 average rating, 145 reviews

A stylish kitchen countertop features a decorative sign reading 'HOME sweet HOME' beside a woven basket filled with assorted items. Nearby, neatly arranged containers for salt and other spices complement the modern aesthetic, while a small succulent plant adds a touch of greenery.

Home in Clearwater

NEW! renovated duplex minutes from the Beach!

Cottage in Indian Rocks Beach

An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.

4.96 out of 5 average rating, 165 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

The outdoor space features a heated pool surrounded by a spacious patio. The clear blue water reflects the sky, with palm trees providing shade nearby. Lounge chairs are placed around the pool for relaxing in the sun.

4.95 out of 5 average rating, 120 reviews

Largo Poolside Paradise Heated Pool 10Min To Beach

Guest suite in St. Petersburg

A spacious sleeping area features a large bed with white linens and a textured blue throw. Natural light filters through two windows adorned with light curtains. Decorative elements, including a small vase, add a subtle touch to the room's design.

4.82 out of 5 average rating, 370 reviews

Cozy St Pete Suite near beaches

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, 398 reviews

Amazing views on beachfront

Family-friendly home rentals with a pool

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, 21 reviews

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

4.96 out of 5 average rating, 49 reviews

An outdoor view reveals a large heated pool surrounded by lush landscaping and palm trees. Lounge chairs are positioned around the pool, with a barbecue area visible to the left. The elegant architecture of the nearby building adds to the inviting community ambiance.

Apartment in Clearwater

Avalon. Clearwater. Cozy condo. Pool view.

A welcoming entrance to The Avalon features a landscaped roundabout with manicured greenery and vibrant flowering plants. A central fountain adds a serene element, while the building's architecture is framed by palm trees and blue skies.

4.93 out of 5 average rating, 89 reviews

Condo Conveniently located to Clearwater Beach

Home in Indian Rocks Beach

5 out of 5 average rating, 11 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat

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.

4.95 out of 5 average rating, 131 reviews

Bright and Spacious 1Bed/1Bath condo.

4.84 out of 5 average rating, 44 reviews

A modern kitchen features an expansive marble countertop with bar seating. Two pendant lights hang above, illuminating the space. Stainless steel appliances are seamlessly integrated, and a sliding glass door opens to a small balcony with outdoor seating for two.

Apartment in Clearwater

Avalon Sun-kissed Boutique: Luxury-free parking

A spacious living room with high vaulted ceilings features a large, comfortable sectional sofa adorned with various colorful pillows. A decorative area rug lies beneath a central coffee table. The wall displays playful artwork, complemented by soft lighting and neutral tones throughout the space.

4.87 out of 5 average rating, 143 reviews

Clearwater Game House! Bowling, Golf, Heated Pool

A modern kitchen is showcased with stainless steel appliances and a central island featuring bar seating. Sleek cabinetry and a bright light fixture enhance the space. Natural light fills the room, emphasizing the clean lines and functional design.