Family-friendly holiday rentals in Sand Key

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

4.97 out of 5 average rating, 136 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.

Flat in Indian Rocks Beach

An aerial view captures a heated pool surrounded by lounge chairs and umbrellas. The pool features a unique shape and is bordered by paver stones. Nearby, a dining area and grill are visible, along with lush greenery framing the space.

4.94 out of 5 average rating, 145 reviews

Heated Pool! Steps 2 beach! Luxurious King bed

Everything is brand new in this completely renovated vacation rental. Located less than a block to the beach and across the street from a park. Enjoy the views of the pool & park from the unit or the private balcony. A luxurious $3,000+ King Puffy Royal Hybrid Mattress provided in the master bedroom will ensure you are sleeping well! Out back is a large HEATED pool, lounge chairs, dining tables, grill, fire pit and more. We provide all your beach needs, towels, umbrella, beach chairs, and more!

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, 100 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!

Flat in Indian Rocks Beach

An aerial view captures the serene coastline and vibrant community of Indian Rocks Beach. The expanse of blue water meets the sandy shore, with buildings and residences lined along the beach. Green parks and water channels are visible, enhancing the coastal atmosphere.

4.96 out of 5 average rating, 118 reviews

Cozy coastal grandmother condo, walk to the beach!

Bright, stylish and quaint. Newly remodeled and furnished to make you feel like you're at your own beach home. Grab your provided beach chair and towel for your short jaunt down to the beach(a football field away) and take a deep breath; let the endless views, waves crashing and sand between your toes take you away. The well appointed kitchen can be used to simply make coffee or a full dinner. Don't feel like cooking? No problem! Indian Rocks Beach offers local coffee, lunch and dinner spots!

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.

4.97 out of 5 average rating, 174 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Superhost

Apartment in Sand Key

5 out of 5 average rating, 4 reviews

CBC 2-18D: Guests welcome! All Amenities Open!

Welcome to Crescent Beach Club 2-18D! ☀️🌻 Prepare to be swept off your feet by this exquisite, recently renovated 18th-floor condo at Crescent Beach Club. Offering breathtaking vistas of the Gulf of America and the Intracoastal Waterway from not one, but three balconies, this property features 2 bedrooms and 2.5 bathrooms. Every inch of this unit exudes luxury, with brand-new coastal furniture and bedding that sets the stage for a serene and welcoming ambiance.

Townhouse in Indian Rocks Beach

A comfortable living room features a dark sectional sofa adorned with vibrant Kraken-themed cushions. Warm light is provided by floor lamps on either side. Large sliding glass doors lead to a balcony with views. A dining area is visible, alongside a small kitchen with a bar.

4.93 out of 5 average rating, 106 reviews

The Kraken-6-pass golf cart! Plus Pool

The Kraken is new with tasteful Kraken decorations to pull the space together. Packed with a big 75" TV, big double queen guest room, and king sized master bedroom. The Kraken is the perfect beach house to get your toes in the water in minutes, the perfect beach community to walk to local cuisine, with the perfect creature comforts of home. The penthouse floor is for families/groups that want to have fun together with epic sunsets perfect for sun downers.

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

4.99 out of 5 average rating, 117 reviews

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

4.95 out of 5 average rating, 133 reviews

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.

Home in Largo

Palm Paradise - Family Amenities+Central Location

Welcome to Palm Paradise! This modern home is perfectly laid out & well equipped, especially for families with children. Whether it's time to relax or play, this extraordinary home has something for everyone! Enjoy those Florida nights in the bohemian inspired outdoor space or heated pool. Gather the group to play mini golf, outdoor bowling, corn hole or one of our many games inside and out. The ultimate vacation awaits you.

4.86 out of 5 average rating, 160 reviews

A cozy bedroom features a spacious bed with crisp white linens, accompanied by decorative pillows. A ceiling fan is installed above, enhancing comfort. Natural light fills the room through the window, which is adorned with greenery and blinds. Nightstands with lamps provide additional lighting.

Flat in Clearwater Beach

Waterfront Coastal Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle in a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more. We are pet friendly! Pet fee is $150 per pet.

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

Apartment in Clearwater Beach

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, 138 reviews

Waterfront Condo | Steps to Clearwater Beach 2King

4.97 out of 5 average rating, 244 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

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

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.

5 out of 5 average rating, 131 reviews

Waterfront Beach House Steps Away from #1 Beach!

4.94 out of 5 average rating, 125 reviews

Flat in St. Petersburg

Waterfront studio! Heated pool and hottub

Apartment in St. Petersburg

A private balcony offers a serene view of the bay, framed by lush palm trees. A glass table and two chairs are positioned for easy enjoyment of the surroundings, while the sparkling water glimmers under a clear blue sky.

4.96 out of 5 average rating, 276 reviews

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!

Cottage in Indian Rocks Beach

The porch features a circular daybed with decorative cushions, accompanied by a small table and two chairs. Direct views of the bright blue sky and nearby palm trees are visible, enhancing the outdoor relaxation space.

4.97 out of 5 average rating, 173 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

4.99 out of 5 average rating, 263 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

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

4.94 out of 5 average rating, 223 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.

Flat in Dunedin

The Coastal Retreat

Bungalow in Indian Shores

4.96 out of 5 average rating, 178 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.96 out of 5 average rating, 181 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

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, 104 reviews

Beach Days & Family Fun - Last Minute Openings

4.97 out of 5 average rating, 419 reviews

Cottage in Dunedin

Walk to Main St and 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

4.93 out of 5 average rating, 171 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

Family-friendly home rentals with a pool

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

Apartment in Belleair Beach

A modern living area is visible, featuring a gray sectional sofa adorned with colorful pillows. A round coffee table is centered on a light floor. Large windows offer views of the beach and ocean, while a dining area for four is positioned nearby, complemented by bright natural light.

4.83 out of 5 average rating, 72 reviews

BBC113 Renovated Beachfront Condo W/Pool

Flat in Indian Rocks Beach

A balcony area showcases comfortable seating arrangements with a table and chairs, offering a view of the sandy beach and ocean. Lush greenery is visible in the background, with palm trees swaying gently in the breeze under a clear blue sky.

4.92 out of 5 average rating, 48 reviews

Luxury Oceanfront Vacation w/ Heated Pool

Apartment in Belleair Beach

The image captures a serene sunset over the Gulf, with vibrant colors reflecting on the water. A heated pool is in the foreground, surrounded by lounge chairs, while the beachfront property frames the scene, creating a peaceful coastal ambiance.

4.88 out of 5 average rating, 91 reviews

Condo On The Beach - Heated Pool - Self Check-in

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.

4.94 out of 5 average rating, 94 reviews

Condo Conveniently located to Clearwater Beach

4.99 out of 5 average rating, 72 reviews

A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.

Cottage in Largo

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

A scenic balcony is visible, featuring a round table surrounded by several chairs. The view highlights the expansive Gulf of Mexico, with clear blue skies and gently rolling waves in the background. A palm tree adds a tropical touch to the beachfront scene.