Family-friendly holiday rentals in Palm Harbor

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, 134 reviews

Coastal Escape: heated saltwater pool & playground

★ 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

Cottage in Tarpon Springs

The exterior of the cabin is showcased, featuring a white façade and a welcoming front porch. Decorated with colorful plants, the walkway leads to the entrance, framed by lush greenery and tall trees providing natural shade.

4.98 out of 5 average rating, 122 reviews

Cooper Cabin: Cute, Adorable, Standalone Studio

Cooper Cabin is a super cute and sparkling clean stand alone studio with a full eat-in kitchen and bath. 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! Located within walking distance of all things Tarpon Springs and just a short 7 min drive to Fred Howard Beach, Cooper Cabin is decorated with fun decor and a relaxing front porch balcony with bistro set. Bikes and beach gear provided!

5 out of 5 average rating, 106 reviews

A cozy living space features a large leather couch with accent pillows and a coffee table. A spacious bed is positioned in the background, complemented by bedside lamps. Light flows in through sliding glass doors, which open to a view of landscaped greenery.

Condo in Palm Harbor

Innisbrook Condo 1st Floor next to Island Course

Host is picking up the 14.1-16.5 Airnbn service fees. Innisbrook Gated Golf Resort we have a 1st floor Condo w/walk-out patio. Close to beaches with family activities, restaurants and dining. You’ll love our place because of the location, the ambiance, the neighborhood, the outdoors space, etc. *Please be advised that the amenities; pools, tennis, golf are only available to owners w/ membership and not guests of AirBnb unless a member is with you. Bars/Restaurants are open to airbnb.

Holiday home in Tarpon Springs

A cozy living room is displayed with a green sofa positioned beside a plant. A coffee table sits at the center, accompanied by a light fixture and a wall art piece. Natural light filters through the window, illuminating the warm wood flooring.

4.97 out of 5 average rating, 126 reviews

Modern Home Great Location

Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

4.82 out of 5 average rating, 136 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.

Guesthouse 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 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, 138 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

4.97 out of 5 average rating, 150 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.

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.

4.93 out of 5 average rating, 132 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!

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, 172 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, 146 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

4.89 out of 5 average rating, 224 reviews

A modern living area showcases a sleek gray couch featuring soft tufting and a white decorative pillow. A circular wooden coffee table, supported by a geometric metal base, rests nearby, providing a casual yet stylish touch to the space.

Home in Allen's Ridge

Cute Lil' House Near Historic Downtown Palm Harbor

They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.

4.79 out of 5 average rating, 163 reviews

Home in Tarpon Springs

Mins to Beach/Studio Home/walk to dwtn/FreeParking

✨ Beautifully remodeled studio in the heart of Tarpon Springs. Just an 8-minute drive to the beach, this cozy retreat was thoughtfully designed with comfort in mind. Featuring a comfy queen bed and a bright, welcoming interior, it’s the perfect spot to relax after exploring the Sponge Docks, downtown, and nearby attractions.

Popular amenities for Palm Harbor family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse 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, 374 reviews

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

4.93 out of 5 average rating, 118 reviews

An outdoor hot tub is positioned beside a wooden deck, featuring steps for easy access. Sunlight reflects off the water, while a lounge area with seating and umbrellas is visible in the background. A welcoming sign marks the entrance to the studio.

Apartment in Largo

Relaxing Coastal Getaway w/ Jacuzzi & Private Yard

4.86 out of 5 average rating, 146 reviews

A studio apartment includes a spacious bed with a light blanket, complemented by a cozy sofa and a festive Christmas tree. Soft lighting creates a warm atmosphere, while large glass doors provide access to natural light. A dresser and TV add functionality to the space.

Home in Holiday

Comfort In Holiday

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.

4.92 out of 5 average rating, 143 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

4.96 out of 5 average rating, 375 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

4.85 out of 5 average rating, 107 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.

Apartment in Clearwater

La Casa Tranquil,1of4 units onsite/ Heated Pool!

4.9 out of 5 average rating, 193 reviews

A serene pool area is surrounded by lounge chairs and palm trees, with a view of the water in the distance. Soft lighting from overhead strings enhances the setting. The pool depth is marked at 5 feet, and a sun umbrella offers shade.

Condo in Dunedin

Waterfront Resort Condo – Gulf, Beach & Bikes

A spacious screened-in patio features comfortable seating arrangements with wicker armchairs, designed for relaxation. A circular table sits at the center, accompanied by a fire pit. The saltwater pool glistens in the background, surrounded by tropical greenery and ample natural light.

4.95 out of 5 average rating, 112 reviews

FREE Heated Pool & Spa l Book your Winter Vacation

Family- and pet-friendly home rentals

Tiny home in Tarpon Springs

A serene sleeping area features a large bed adorned with multi-colored striped blankets and a cozy yellow throw. Natural light fills the space through two windows, illuminating the wooden accents and white walls.

4.88 out of 5 average rating, 288 reviews

Driftwood Surf Shack

Guesthouse in Town 'n' Country

4.99 out of 5 average rating, 290 reviews

Entire Guest House near Tampa airport

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.

Apartment in Dunedin

The Coastal Retreat

4.89 out of 5 average rating, 232 reviews

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.

Guesthouse in Clearwater

Cottage on Pinellas Bike Trail

4.9 out of 5 average rating, 121 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.

Apartment in Ozona

Bright and Airy Ozona on the Gulf

4.97 out of 5 average rating, 416 reviews

A tranquil bedroom features a spacious bed with soft, white linens and a light throw. The headboard made of natural materials adds texture against a soothing blue wall. Two nightstands with lamps flank the bed, enhancing the cozy atmosphere of the space.

Cottage in Dunedin

Walk to Main St and Waterfront, Mins to Beaches

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, 291 reviews

Sweet & Simple guest suite Close to Everything.

Condo in Clearwater Beach

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 309 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 135 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

4.99 out of 5 average rating, 261 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

4.87 out of 5 average rating, 71 reviews

Valencia Manor, your Favorite Florida Pool Home!

4.89 out of 5 average rating, 57 reviews

A serene outdoor pool area is highlighted, featuring a crystal-clear solar-heated pool. Two lounge chairs are positioned alongside the pool, with lush greenery providing a natural backdrop. A stacked stone waterfall adds a tranquil touch to the secluded space.

Home in Fox Chase

Paradise in Palm Harbor l Free Heated Pool

5 out of 5 average rating, 6 reviews

Home in Crystal Beach

Relax & Play! Pool + Game Room by Crystal Beach

5 out of 5 average rating, 38 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.

4.95 out of 5 average rating, 160 reviews

Tropical Getaway w/Heated Pool & King Beds