Family-friendly holiday rentals in Clearwater

5 out of 5 average rating, 125 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

4.98 out of 5 average rating, 187 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's w/ Sling & Roku. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

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.

Guest house in Palm Harbor

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

4.86 out of 5 average rating, 162 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

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

Flat 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

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.

4.94 out of 5 average rating, 120 reviews

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.

4.85 out of 5 average rating, 131 reviews

An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.

Guest house in Dunedin

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Guest suite in St. Petersburg

A welcoming exterior showcases a bright yellow door framed by grey walls and distinctive column accents. Lush green grass surrounds the entrance, complemented by flowering shrubs near the pathway. Two large windows allow natural light to illuminate the space, creating an inviting first impression.

4.91 out of 5 average rating, 284 reviews

Sweet & Simple guest suite Close to Everything.

Keep it sweet & simple at this peaceful and centrally-located private room close to downtown and the beaches. The room has it's own entryway from outside and boasts, TV, Wi-Fi, a full private bathrooms. The walk in closet space functions as a breakfast nook with mini refrigerator, microwave, and the necessary basic breakfast utensils. The room is also pet-friendly and close to major highways and transportation hubs. Come and call this space home for your stay in Saint Petersburg.

Guest house in Clearwater

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.

4.97 out of 5 average rating, 144 reviews

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.

4.93 out of 5 average rating, 170 reviews

A cozy sleeping area features a compact bed with a navy blue coverlet. Two rolled towels are neatly arranged on the bed. Natural light filters through two windows adorned with white blinds, and a light-colored nightstand sits beside the bed, illuminated by a small lamp.

Guest suite in Tampa

Shabby Chic Studio in West Tampa.

This private studio is located in the West Tampa area next to Raymond James Buccaneer Stadium. Very close to downtown, Midtown, Tampa airport, International plaza , the interstate, and to popular restaurants such as Flemings, Ocean Prime and Armature works. It comfortably accommodates up to 2 people. This shabby chic hideaway is ideal for touristic or work/study related trips. Every detail has been well-thought and curated to deliver the best experience for our guests.

4.99 out of 5 average rating, 210 reviews

The modern kitchenette features sleek cabinetry, a stainless-steel refrigerator, and a countertop with three black bar stools. A flat-screen television is positioned nearby, and natural light is observed reflecting off the tiled floor, enhancing the open layout.

Flat in Clearwater

Welcome to your cozy studio!

This charming furnished studio apartment is the perfect blend of comfort and convenience, offering everything you need for a delightful living experience: *Fully Furnished *Comfortable Sleeping Area *Equipped Kitchenette *On-Site Laundry Room *Private Parking Space *Private Patio Prime Location: Conveniently located close to shops, restaurants, parks and just 10 minutes away from the breathtaking Clearwater Beach

Popular amenities for Clearwater family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest house in St. Petersburg

A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.

4.84 out of 5 average rating, 365 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

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.

Guest house in Dunedin

Tiki Hut Cottage

4.91 out of 5 average rating, 385 reviews

An outdoor area is equipped with a hot tub and features wooden seating nearby. A sign reading 'Welcome to The Pelican Pad' is displayed on a wooden wall. Large glass doors offer a view of the indoor living space.

Guest suite in Seminole

Coastal Bliss with hot tub - 4 miles to beaches

4.84 out of 5 average rating, 104 reviews

A fenced backyard features a heated swimming pool surrounded by four lounge chairs and two umbrellas. Lush greenery is present in the background, offering shade and a private feel. Sunlight reflects off the clear water, creating a serene outdoor space for relaxation.

Home in Largo

Villa Bella with Heated Pool

4.86 out of 5 average rating, 106 reviews

A shared pool area features a refreshing blue pool surrounded by light-colored tiles. Lounge chairs are positioned for comfort, flanked by palm trees and potted plants. An umbrella provides shade, and a small bar area is visible in the background, enhancing the outdoor ambiance.

Flat in Clearwater

La Casa Tranquil,1of3 units onsite/pool/near beach

4.99 out of 5 average rating, 335 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

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, 160 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

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, 116 reviews

3 Bedroom Waterfront Paradise Sleeps 8

Family- and pet-friendly home rentals

Flat 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.

4.95 out of 5 average rating, 197 reviews

Vintage Florida Beach Efficiency

A cozy outdoor fire-pit area is surrounded by colorful seating. Decorative stones cover the ground, leading to a grill and the inviting glow of flames. A pool and shaded area can be seen in the background, set against a twilight sky.

4.97 out of 5 average rating, 162 reviews

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

Guest house in Town 'n' Country

4.99 out of 5 average rating, 267 reviews

Entire Guest House near Tampa airport

Serviced apartment in Dunedin

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.

4.94 out of 5 average rating, 221 reviews

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

4.92 out of 5 average rating, 274 reviews

A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.

Home in Barrington Hills

Wonderful family friendly home in Dunedin FL

4.92 out of 5 average rating, 128 reviews

A light-filled living area is furnished with a comfortable grey sofa and two wooden chairs. A round coffee table sits in the center on a natural fiber rug. A wall-mounted TV displays a scenic view, while large windows with blinds allow natural light to enter.

Home in Largo

12 Mins to Beach | Patio&Grill | Fenced Yard

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.

4.88 out of 5 average rating, 226 reviews

Cottage on Pinellas Bike Trail

Family-friendly home rentals with a pool

The living room features a spacious sectional sofa in soft blue, complemented by decorative pillows. A large flat-screen TV is mounted on a textured wall, while a coffee table is centered in the area. A wall art piece depicting ocean waves enhances the coastal theme.

4.82 out of 5 average rating, 119 reviews

Seaside Paradise at Clearwater - Resort Style

4.98 out of 5 average rating, 94 reviews

Lovely Condo minutes from beach & King bed

4.76 out of 5 average rating, 157 reviews

A heated pool is surrounded by tropical palm trees and lounge chairs, offering a refreshing space for relaxation. Colorful umbrellas provide shade, and a pink flamingo float is situated in the water. The evening sky showcases vibrant hues of pink and purple.

Flat in Clearwater Beach

Renovated 2025 - Retro Beach Oasis with Color Pop

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.

4.97 out of 5 average rating, 114 reviews

Cozy Retreat, private unit, NO PETS

A vibrant outdoor space features a heated pool surrounded by tropical plants and lounge areas. Colorful floats adorn the water, while a built-in barbecue and seating area provide options for relaxation and entertainment. Soft lighting enhances the inviting atmosphere during twilight.

4.86 out of 5 average rating, 115 reviews

Heated Pool, Golf, FUN! Clearwater Game Villa

4.89 out of 5 average rating, 239 reviews

A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.

Flat in Clearwater Beach

Waterfront Modern Chic #1 Clearwater Beach

Flat 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, 146 reviews

Triplex- walk to beach, heated pool, bikes