Family-friendly holiday rentals in Crystal Beach

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.

5 out of 5 average rating, 152 reviews

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

4.97 out of 5 average rating, 175 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

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Cottage in Tarpon Springs

The front exterior of Cooper Cottage features a welcoming porch with two black rocking chairs and potted plants. A pathway leads to the entrance, while large windows allow natural light to illuminate the space. Lush trees provide shade and a tranquil atmosphere.

4.99 out of 5 average rating, 179 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

4.9 out of 5 average rating, 125 reviews

A spacious living area features large windows offering views of lush greenery. A wooden coffee table is centered between two leather sofas and a light-colored couch. A ceiling fan overhead enhances air circulation, while the adjoining kitchen is highlighted by wood accents and modern appliances.

Flat in Ozona

Bright and Airy Ozona on the Gulf

Welcome to beautiful Ozona. Gulf of Mexico at your front door! Pinellas trail just moments away. Walk/ bike to local Seafood, BBQ & Bars. Stunning palm tree and lush green grass property. Only a couple miles to lively Downtown Dunedin, Honeymoon Island and Clearwater Beach! Relax in this custom Florida apartment in a triplex. Features a newly renovated custom kitchen with granite counter tops, new floors and bathroom. A brand new King mattress. A bright, clean and airy home away from home.

5 out of 5 average rating, 204 reviews

The guesthouse is set on a green lawn, surrounded by trees. A friendly horse grazes nearby, accompanied by a variety of free-ranging chickens and ducks. The exterior features a welcoming porch with wooden railings, adding to the farm's relaxed atmosphere.

Farm stay in Zephyrhills

HORSE FARM Retreat, Newer Built Private Guesthouse

Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

5 out of 5 average rating, 109 reviews

A private backyard pool area is featured, showcasing a clear blue in-ground pool surrounded by lounge chairs and sunbeds with striped cushions. Lush greenery and potted plants add a tranquil touch, while a shaded umbrella stands at one end for comfort.

Guest house in Ozona

Private pool, steps to gulf, fishing, bike trails

Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

A comfortable living area is showcased with a beige sofa adorned with colorful pillows and two green accent chairs. A ceiling fan provides airflow, and natural light filters through large windows. The open layout connects to the kitchen area, creating a bright and inviting atmosphere.

4.92 out of 5 average rating, 143 reviews

Cozy Retreat! Walk to Crystal Beach/Park

Cozy Crystal Beach Retreat – Pet Friendly Enjoy this charming 2BR, 1BA home with queen beds and a pull-out sofa. Pets welcome with fee! Relax in the fully fenced backyard with picnic table, perfect for outdoor meals or your furry friend to play. Walk to the water or explore the nearby Pinellas Trail. Just minutes to downtown Dunedin (7 mi), Honeymoon Island (7.5 mi), Clearwater Beach (13 mi), and Tampa Intl Airport (22 mi). Ideal for couples, families, or a relaxing getaway!

Guest house in Zephyrhills

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A coffee table sits in front, with a tray positioned on top. The kitchen in the background includes a black refrigerator and a dining table surrounded by chairs, illuminated by pendant lighting.

5 out of 5 average rating, 106 reviews

Under The Oaks Cottage

A charming cottage nestled beneath majestic oak trees, combining country living within reach of city amenities. This comfortable space features one bedroom with a king size bed along with built in bunk beds in the main living area. Savor a morning cup of coffee in the screened back porch while enjoying the beautiful tropical foliage. Chickens, goats, cows, and a horse forage nearby. You could possibly be entertained by the goats playing on the roof-tops.

4.98 out of 5 average rating, 128 reviews

An aerial view of the tropical backyard reveals a spacious layout with colorful lounge chairs and umbrellas scattered across a gravel surface. Several dining areas, outlined by lush greenery, create inviting spots for relaxation and gatherings, surrounded by the tranquility of the natural setting.

Home in Tarpon Springs

Tropical Pool Retreat in Tarpon Springs

Welcome to our Tropical Oasis, a polished yet warm and welcoming vacation retreat nestled in the charming neighborhood of Tarpon Springs, Florida. - Spacious 3-bedroom home for up to 8 guests - Tastefully decorated living area with smart TVs - Heated saltwater pool and screened lanai - Fully-equipped game room with table tennis and foosball - Complimentary bikes for exploring - Close to Tarpon Springs Sponge Docks and Fred Howard Park

The image captures a serene view of the canal with calm, reflective waters. Lush greenery lines the banks, while several boats are seen docked along the shore. Bright sunlight illuminates the scene, highlighting the tranquility of the waterfront setting.

4.98 out of 5 average rating, 110 reviews

Tarpon Lake Escape LLC

Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Townhouse in Crystal Beach

A fenced outdoor space features a fire pit surrounded by four blue Adirondack chairs, set on sandy ground. Lush greenery and tall palm trees enhance the tranquil atmosphere, while a grill is visible nearby, providing options for outdoor cooking and relaxation.

4.94 out of 5 average rating, 177 reviews

Relaxing Pond View - Beaches - Bikes - Fire Pit

* Honeymoon/Caladesi Islands (10min) * Pinellas Trail - bike/walk/run * Walk/bike to St Joseph Sound (great for sunsets) * Downtown Dunedin & Tarpon Sponge docks (10min) * Screened patio w/fan & lights * Fenced yard w/grill, view of the pond, a fire pit * Beach chairs, towels and beach toys provided- even some fishing poles for the pier! * 2 adult bikes provided

A heated pool is surrounded by lush palm trees, providing a sense of seclusion. A stone statue and decorative elements are featured along the pool's edge. Sunlight reflects off the water, creating a serene atmosphere in this private outdoor oasis.

4.99 out of 5 average rating, 159 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

Popular amenities for Crystal Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 203 reviews

A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.

Cottage in Safety Harbor

Harbor Oasis | Hot Tub | Private | Lush Backyard

Tiny home in Ybor City Historic District

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

4.99 out of 5 average rating, 583 reviews

Cozy AF Tiny-House Oasis

4.94 out of 5 average rating, 118 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 Palma Ceia

The Jungalow SOHO - Pool/Hot Tub

4.98 out of 5 average rating, 137 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

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

4.91 out of 5 average rating, 153 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

4.97 out of 5 average rating, 156 reviews

Home in Largo

[Top Pick] Family Fun Getaway | Heated Pool

4.96 out of 5 average rating, 376 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

4.98 out of 5 average rating, 364 reviews

A spacious outdoor pool area is visible, featuring a large swimming pool surrounded by lounge chairs and seating areas. A pergola provides shade, while decorative planters add greenery. The area is enclosed by a privacy fence, creating a secluded retreat.

Home in Seminole

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

Family- and pet-friendly home rentals

Superhost

4.63 out of 5 average rating, 8 reviews

Coastal Sun & Play: Heated Pool Home w/ Game Room

4.86 out of 5 average rating, 7 reviews

Home in Crystal Beach

Modern 2BR near Beaches – Kitchen + Private Yard

4.99 out of 5 average rating, 363 reviews

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

Walk to Downtown and Waterfront - Private Yard

4.99 out of 5 average rating, 307 reviews

The tiny home is set amidst a lush forest backdrop, featuring a welcoming entrance that is framed by large windows. A spacious wooden deck is adorned with comfortable seating, including two bright blue chairs and two red chairs. A black hammock hangs between trees, inviting relaxation.

Campsite in Thonotosassa

The Palm Tree Getaway

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

4.93 out of 5 average rating, 122 reviews

Lakefront home near beaches w/ waterview, pets ok

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 139 reviews

Private pool suite in heart of Tarpon Springs!

Tiny home in Tarpon Springs

A modern sleeping area is defined by flowing curves and a bright green and white color scheme. Two spacious beds feature plush pillows and decorative accents. Soft lighting highlights the unique wall design and climate control unit, contributing to a fresh and clean ambiance.

4.94 out of 5 average rating, 160 reviews

Luxury Modern Tiny Home

A cozy outdoor gathering area is surrounded by a circular arrangement of gravel. Several chairs are positioned around a central fire pit, with warm string lights softly illuminating the space. Tall plants and decorative pots accentuate the area, providing a welcoming atmosphere.

4.96 out of 5 average rating, 55 reviews

Crystal Beach Cozy Cottage

Family-friendly home rentals with a pool

Superhost

Home in Ozona

5 out of 5 average rating, 4 reviews

NEW Remolded luxury retreat, 5BR

4.83 out of 5 average rating, 6 reviews

Pool, Games & More—Fun for Everyone!

4.91 out of 5 average rating, 55 reviews

Private Pool! Tropical Beaches! Palm Harbor, FL

5 out of 5 average rating, 12 reviews

Honeymoon Luxury Residence with Heated Pool &Sauna

4.93 out of 5 average rating, 94 reviews

A screened patio surrounds the inviting pool, providing views of the waterfront. Sunlight glimmers on the clear water, and grassy areas border the pool deck. Nearby boat docks are visible, enhancing the serene atmosphere by the water.

Home in Ozona

Luxe Private Waterfront Getaway with Pool in Ozona

5 out of 5 average rating, 9 reviews

Home in Dunedin

WOW! Dunedin Coastal POOL Home-beaches-eateries

5 out of 5 average rating, 43 reviews

A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.

Villa in Fox Chase

Coastal Cottage

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.