Family-friendly holiday rentals in Dunedin

4.97 out of 5 average rating, 131 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.

Guesthouse 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, 160 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, 140 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.

4.93 out of 5 average rating, 273 reviews

A spacious sleeping area features a large bed with a white comforter and decorative throw. A modern lamp illuminates a side table. Soft blue walls complement the artwork depicting a beach scene, while a cozy chair adds a comfortable seating option.

Guest suite in Dunedin

Downtown Coastal Studio, close to great beaches!

The studio has a bright and airy atmosphere, clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin in walking distance to the Pinellas Trail and Main St. Simply park your car and enjoy town on foot or rent a bike and cruise around. We are close to Honeymoon Island and Clearwater Beach. Beach towels, chairs, cooler, and umbrella are provided. There is also a park across the street with a nice path to stroll along the water or take in the sunset.

4.84 out of 5 average rating, 126 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.

4.89 out of 5 average rating, 217 reviews

A private patio area features tile flooring and a wooden fence offering seclusion. A small round table with two chairs is placed in the center, surrounded by lush potted plants. Vertical planters are attached to the wall, enhancing the greenery.

Guest suite in Dunedin

Dunedin Suite West, near Pinellas Trail/beaches

Dunedin Suite West is modern and spacious with a full kitchen and private patio area out back. You will find it clean, comfortable, and convenient staying here. The suite is a 15 minute drive to Honeymoon Island and Clearwater Beach, ranked some of the nicest beaches in the world. Beach supplies included. You can rent bikes and bike the Pinellas Trail. Pinellas Trail, Blue Jays Stadium, and Main St with tons of restaurants, breweries, art, and shops are all within walking distance.

4.95 out of 5 average rating, 100 reviews

A welcoming outdoor space is highlighted by two red lounge chairs, adorned with floral cushions, positioned on a paved area. Lush greenery, including banana plants, frames the cottage-style villa, while a small seating area is visible in the background, providing a tranquil setting.

Cottage in Dunedin

Adorable Villa 1 min to Downtown Dunedin

Welcome to our 1/1 cottage-style villa, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

4.97 out of 5 average rating, 140 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.

4.99 out of 5 average rating, 352 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

Steps to Main Street, short walk to Dunedin's waterfront. Minutes to beaches. Private yard with grill. Enjoy beautiful décor and two king suites. Stroll to Dunedin's restaurants, breweries, shops, and live music. Enjoy stunning waterfront sunsets or drive minutes to award-winning beaches such as Honeymoon Island and Clearwater Beach. Sleeps 6. Loaded with beach and kids’ gear for a seamless escape. Treat yourself and book this Dunedin guest favorite by Lucky Guest today.

4.94 out of 5 average rating, 221 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

Studio apartment. Light airy Coastal Eclectic décor. Walk in closet, full size bath, Fully equipped kitchen . Key west style tropical courtyard with fish pond. Off street parking . Gas grill and outdoor dining area. One block off the Pinellas Bike trail, walking/biking to historic downtown Dunedin, Toronto Blue Jays spring training. Minutes to the 3 of the country's best beaches! Clearwater Beach, Honeymoon Island, and Caladesi Island.

4.96 out of 5 average rating, 195 reviews

A compact kitchen area includes a white refrigerator, an oven, and a microwave, all arranged neatly against light cabinetry. A circular clock in red and black adorns the wall, while a small black dining table with two chairs is positioned in front. Glassware and kitchen accessories are displayed on open shelving.

Apartment in Dunedin

Cozy Apartment Overlooking Downtown Dunedin

Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. Second floor 1 bedroom apartment is totally renovated. Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more. Sit on the front porch and see all Dunedin has to offer.

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.

Guesthouse in Dunedin

Tiki Hut Cottage

This unit private vacation rental is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Spacious living area with a kitchenette. The property is an acre of lush tropical plants Conveniently located to the downtown & beach.All our units are non-smoking and vaping.

Popular amenities for Dunedin family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 111 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

Cozy Studio w/ jacuzzi 5 mi to Beach - with yard

4.95 out of 5 average rating, 100 reviews

A serene outdoor space features a winding pathway of stone slabs leading to a decorative garden statue surrounded by lush palm trees. The natural landscaping provides privacy and a peaceful atmosphere within the courtyard.

Apartment in Largo

Hidden Oasis #3, just a few mins to the beach

4.88 out of 5 average rating, 171 reviews

A private outdoor pool is surrounded by a spacious patio, featuring tropical landscaping and palm trees. The pool area includes a shallow ledge for lounging. The exterior of the home, with light-colored stucco, is visible in the background alongside a securely fenced yard.

Home in Largo

The Paradise Cove No. 1

4.95 out of 5 average rating, 126 reviews

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.

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages

4.85 out of 5 average rating, 103 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,1of3 units onsite/pool/near beach

Guesthouse in St. Petersburg

4.97 out of 5 average rating, 186 reviews

Centrally Located Cozy 1-bed Private Cottage!

4.86 out of 5 average rating, 310 reviews

An inviting balcony view overlooks a spacious pool area and the intercoastal waters, framed by palm trees. A light-filled living area features comfortable furnishings and a television, while the dining space and kitchen are visible, providing a warm atmosphere for relaxation and enjoyment.

Condo in St. Petersburg

Breathtaking Waterview & Pool View Condo

4.97 out of 5 average rating, 386 reviews

A clear blue pool is surrounded by lush greenery, including palms and other tropical plants. A red umbrella provides shade over a seating area nearby, while lounge chairs are positioned along the pool's edge, inviting relaxation in a serene outdoor setting.

Guest suite in Largo

Private Pool, Jacuzzi, Walk to Beach.

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 159 reviews

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.

Home in Clearwater

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

Guesthouse in Town 'n' Country

4.98 out of 5 average rating, 259 reviews

Entire Guest House near Tampa airport

4.92 out of 5 average rating, 272 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

4.91 out of 5 average rating, 217 reviews

The spacious studio cabin features wooden accents and high ceilings with exposed beams. Large windows allow natural light to fill the room. A comfortable sofa, a flat-screen TV, and a queen bed are present, alongside a small side table and two chairs.

Apartment in Dunedin

Downtown Dunedin B&B - Rustic Cabin with Pool

4.88 out of 5 average rating, 223 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

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, 134 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.

4.93 out of 5 average rating, 112 reviews

Luxury Modern Tiny Home

4.89 out of 5 average rating, 401 reviews

A spacious bedroom features a large bed adorned with a patterned blue and white bedspread. Soft lighting from a bedside lamp provides a warm ambiance. A ceiling fan and two windows with sheer curtains contribute to the bright atmosphere, while a decorative piece hangs on the wall.

Apartment in Clearwater

Comfy Guesthouse # 1 - 4 miles to Clearwater Beach

Family-friendly home rentals with a pool

4.79 out of 5 average rating, 135 reviews

A covered swimming pool area features a clear and inviting pool, surrounded by a spacious patio with tiled flooring. Large glass doors allow natural light to flood the space, while lounge chairs are positioned nearby, offering a comfortable spot to relax.

Home in Dunedin

House of Relaxation

An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.

4.95 out of 5 average rating, 129 reviews

Bright and Spacious 1Bed/1Bath condo.

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, 113 reviews

Cozy Retreat, private unit, NO PETS

A modern living area features a large television mounted on the wall, framed by a stylish red console. Two comfortable chairs and a table are arranged in front of a sliding glass door, which opens to a private balcony with tropical greenery visible outside.

4.95 out of 5 average rating, 146 reviews

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

4.95 out of 5 average rating, 118 reviews

The outdoor space features a heated pool surrounded by a spacious patio. The clear blue water reflects the sky, with palm trees providing shade nearby. Lounge chairs are placed around the pool for relaxing in the sun.

Home in Largo

Largo Poolside Paradise Heated Pool 10Min To Beach

4.99 out of 5 average rating, 143 reviews

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

Home in Palm Harbor

Tropical Oasis Retreat w/ Heated Pool

The heated swimming pool is surrounded by palm trees and lounge chairs, offering a relaxing atmosphere. The pool area features a spacious deck with light-colored paving, while nearby buildings provide a serene backdrop, enhancing the inviting outdoor setting.

4.81 out of 5 average rating, 164 reviews

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES