Family-friendly holiday rentals in East Lake

4.99 out of 5 average rating, 103 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

+Spacious family retreat on lake +Free heated pool +Huge last-minute discounts +Big deck, BBQ, dining & firepit +Private backyard lakefront +3 bedrooms, 1 king, 1 queen, 2 twin +3 full baths +Easy to cancel +Pet friendly +Fishing +Games +Quiet serene safe +5 minutes to Gulf sunsets +5 min to Sims Park +20 min to Tarpon Springs +39 min to Tampa airport +50 min to Busch Gardens +5 min to restaurants +Fully equipped kitchen +Free parking & garage +Washer-Dryer +Work area +Hi-speed WIFI +Smart TVs

4.92 out of 5 average rating, 285 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 Dunedin

Wonderful family friendly home in Dunedin FL

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

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.

5.0 out of 5 average rating, 175 reviews

Coastal Escape: Heated Pool, Playground&Family fun

★ 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

4.99 out of 5 average rating, 132 reviews

Villa in Palm Harbor

Palm Haus • Heated Pool • Near Beach • Game Room

Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

4.96 out of 5 average rating, 205 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

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, 132 reviews

Lakefront home near beaches w/ waterview, pets ok

Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

4.96 out of 5 average rating, 111 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

Paradise!Renovated waterfront pool home.Sunsets!

Sunsets to die for! Remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard & and spotting dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops. New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys. Fishing rods.Bonfire pit.Grill.Heated pool for a fee. Portable crib,stroller, high chair. Come,relax&enjoy No hurricane damage!

4.96 out of 5 average rating, 119 reviews

A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.

Farm stay in Odessa

Cabin 3 - Nasturtium Nest

Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay. We look forward to seeing you on the Farm!

4.92 out of 5 average rating, 155 reviews

Home in Holiday

Sunny Pool Home • Near Tarpon & Beaches

🌴Make yourself at home at Sun-Water House, a family-friendly and pet-friendly retreat made for sunny pool days and relaxed evenings. Enjoy the privacy of a fully fenced backyard, share a meal outdoors, or take the provided beach kit on your next adventure. With comfortable interiors and easy access to Tarpon Springs, nearby Gulf beaches, and many Florida Gulf Coast destinations to discover, it’s the perfect home base for your getaway. ✨ Book your stay and start planning your escape!

4.78 out of 5 average rating, 107 reviews

Chic|Pool|PuttingGreen|Beaches

Enjoy a relaxing family getaway in the Sunshine State! Spend days relaxing on the beach and enjoying outdoor fun for the whole group with a bounce house, putting green, and more at this stylish home. Whether you’re traveling with family and friends or on business, this is a great place to discover the beautiful. Clearwater Beach area. 8 Min Walk to Saint George Lake 12 Min Drive to Wall Springs Park 22 Min Drive to Clearwater Beach.

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, 116 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

4.87 out of 5 average rating, 162 reviews

A spacious outdoor area features a heated private pool surrounded by a screened lanai. Lounge chairs are positioned nearby, and a dining set provides a space for meals. Lush greenery is visible in the background, enhancing the tranquil atmosphere.

Home in Tarpon Springs

Pelican House, Game Room, Pool, 5 min to Beach

Escape to your private 1900+ sq ft coastal retreat, just a 5-min drive from Sunset Beach! This family-friendly home comfortably sleeps 8 and features a sparkling heated saltwater pool, a fully-equipped game room with a foosball table, and a dedicated workspace. Enjoy modern amenities and endless entertainment in this beautifully renovated home, perfect for your next vacation.

Popular amenities for East Lake family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 388 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

4.93 out of 5 average rating, 135 reviews

FREE Heated Pool & Spa l Book your Winter Vacation

4.84 out of 5 average rating, 149 reviews

The illuminated pool takes center stage under the night sky, emitting a tranquil green glow. Surrounding the pool is a spacious deck, featuring lounge chairs and a table for outdoor gatherings, complemented by well-maintained landscaping in the background.

Home in Oldsmar

Hot Tub, Heated Pool, 2 Master Suites, Beach

4.92 out of 5 average rating, 132 reviews

A screened-in outdoor area features a heated pool and spa accompanied by a spacious dining table set for eight. Vibrant glassware and dining plates are arranged, capturing bright colors against the backdrop of lush greenery and a clear sky.

Home in Dunedin

Luxury home ~ Heated pool, hot tub, TWO kitchens

4.91 out of 5 average rating, 236 reviews

A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.

Home in Town 'n' Country

Rooms with a Pool

4.96 out of 5 average rating, 204 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

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.

4.9 out of 5 average rating, 174 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

4.97 out of 5 average rating, 111 reviews

A spacious outdoor area features a hot tub with bubbling water, surrounded by a screened patio. A swimming pool gleams in the sunlight, while a vibrant tree house play area with a slide and swing set adds a colorful touch to the yard.

Home in Spring Hill

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 135 reviews

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

Home in Dunedin

Heated saltwater pool|Spacious 4BR/3BA|

5.0 out of 5 average rating, 101 reviews

A screened-in heated pool area is highlighted, featuring a clear blue pool surrounded by a spacious deck. Comfortable seating is arranged nearby, and floating toys add a playful touch. The enclosure provides a bright and airy feel with natural light streaming in.

Home in New Port Richey

Relaxing Beach-Theme Pool Home!

4.95 out of 5 average rating, 136 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

4.94 out of 5 average rating, 201 reviews

Heated Pool 4 bed 7 miles to Honeymoon Island.

4.99 out of 5 average rating, 127 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.

Guesthouse in Ozona

Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl

4.93 out of 5 average rating, 121 reviews

Home in Clearwater

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

4.73 out of 5 average rating, 117 reviews

A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.

Home in Oldsmar

Private Pool Home Near Clearwater & Tampa

4.92 out of 5 average rating, 12 reviews

Home in Oldsmar

Oldsmar Oasis

Family-friendly home rentals with a pool

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.94 out of 5 average rating, 121 reviews

Private pool, Golf Cart, Completely Renovated!

4.93 out of 5 average rating, 152 reviews

A screened-in patio features a heated swimming pool, surrounded by white decking. The pool offers a view of the canal with palm trees and neighboring properties beyond. The tranquil outdoor space is complemented by a backyard with swings and a dock visible in the background.

Home in Town 'n' Country

Waterfront Resort with HEATED POOL!

4.99 out of 5 average rating, 106 reviews

A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.

Guesthouse in Westchase

Cottage in Paradise.

Holiday home in Safety Harbor

Heated Pool • 4BR • Near Clearwater Beach

4.84 out of 5 average rating, 100 reviews

4.95 out of 5 average rating, 95 reviews

A screened pool area showcases a clear blue pool featuring a dolphin design at the bottom. The surrounding patio is designed with light-colored tiles, and lush greenery is visible beyond the enclosure, contributing to a private outdoor atmosphere.

Home in New Port Richey

Cozy Home, Country Setting, Close to Gulf Beaches

A spacious living area features a large grey sectional sofa adorned with orange and blue accent pillows. A marble coffee table sits in front, while a ceiling fan is visible above. Light enters through large windows, illuminating the open layout connecting to a dining area.

4.96 out of 5 average rating, 50 reviews

The Coastal Calm - Entire Unit

4.92 out of 5 average rating, 13 reviews

Condo in Oldsmar

Short Drive to Clearwater Beach | Heated Pool |