Family-friendly holiday rentals in Redington Beach

4.92 out of 5 average rating, 169 reviews

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

Condo in Treasure Island

Waterside Studio in the heart of TI, walk to beach

Location!!! This charming 2nd floor studio is located in the heart of legendary Treasure Island on the Intracoastal waterway of Boca Ciega Bay, only 3-7 min walk from the beautiful Gulf beaches, restaurants, shopping, and many great beach bars. Relax in the heated pool, have a cookout with the grills and screened waterfront cabana, complete with TV and minifridge, and watch the sunset or fish on one of two docks as dolphins frolic in the warm Gulf waters around you! Your perfect vacation awaits!

Bungalow in Indian Shores

The exterior of a bungalow is surrounded by lush tropical greenery, featuring large leaves and colorful plants. A bright blue wall enhances the entrance, which is flanked by a window. A gravel pathway leads to the door, contributing to a serene environment.

4.93 out of 5 average rating, 237 reviews

Private Beach 2BR Bungalow *heated POOL* PETS ok

PRIVATE BEACH OPEN!!! ENJOY your own bungalow! (NOT a condo - no crowded elevators, hallways, lobby areas) Barrett Beach Bungalows preserves the traditional Florida beach endearments in style with 4 charming bungalows. Why spend your Florida vacation in a busy crowded hotel? DOLPHIN BUNGALOW is ONLY 50 steps to beach, sits behind beachfront bungalow but not beachfront. ALL Guests enjoy heated beachfront pool, lounge chairs, umbrellas, fire pit, volleyball, toys. Fully equipped, super clean!

4.86 out of 5 average rating, 141 reviews

Island Chic Cutie @theBeach@HeatedPool

Great studio located few steps to the Gulf of America. Most everything you need for the beach or pool has been provided, The space is very convenient to great restaurants, grocery stores and nightlife. The neighborhood around the area is really nice and safe. There is a park next door with basketball and outdoor gym equipment plus kids play areas as well. You'll love it here, everyone does. We provide cozy essentials. Some condos being updated inside. Our lower than usual price reflects that.

An outdoor swimming pool is surrounded by a well-maintained paved area and vibrant landscaping. Palm trees provide shade near the pool, while the adjacent building features two levels with balconies overlooking the area. The inviting water reflects sunlight under a clear blue sky.

4.8 out of 5 average rating, 249 reviews

Beautiful Studio on the paradise white sand beach!

The studio at Royal Orleans is a perfect holiday accommodation across from the lovely Redington Beach. The studio offers a sitting area and a kitchen complete with a dishwasher and a refrigerator. A flat-screen TV with cable channels is provided. There is a private bathroom with a bathtub shower. The bed is queen size. The apartment complex has a lovely outdoor swimming pool with a lounge area. Redington Beach is a great choice for travelers interested in sunbathing, swimming and relaxing.

Condo in Redington Shores

A serene beach scene stretches across the horizon, featuring soft, sandy shores against a calm, azure ocean. Gentle waves lap the beach, while a few people walk along the water's edge, under a clear blue sky.

4.84 out of 5 average rating, 270 reviews

Beach Front Condo 3 bathrooms 3 bedrooms/5 beds

My place is on the beach, with great views of the ocean from our private balcony and spectacular sunsets in the evening. There are good restaurants within walking distance. The pool and the hot tub are heated all year round. There are 3 double bedrooms, each with a private bathroom. Large Lounge/Dining Room, fully equipped kitchen, 2 Air Conditioning units fully servicing the entire apartment and Ceiling fans in all rooms. 40 X 20ft. heated pool and 10 X 8ft hot tub right next to the beach.

A cozy sleeping area includes a spacious bed dressed in white, adorned with colorful striped and patterned accents. A stylish sofa complements the room, while wooden cabinets provide storage. Wall art and decorative elements add visual interest to the neutral surroundings.

4.8 out of 5 average rating, 222 reviews

Gulf view Condo with pool in Clearwater/St. Pete

Located between Clearwater Beach & St. Pete Beach, this fully furnished Studio features a full kitchen with a full-sized stainless steel refrigerator and dishwasher, granite countertop, microwave, kitchenware, a Queen bed, a queen size sleeper sofa, closet space, and new AC. This quaint 35-unit resort condo offers a heated pool with tables, lounge chairs and gas grill within a smoke-free tropical courtyard. Just step out the front door for a view of the gulf & 3 mins. walk to the beach.

4.93 out of 5 average rating, 126 reviews

A private outdoor deck is shown with a mix of seating areas. A cozy sectional sofa is paired with square coffee tables, surrounded by decorative chairs. A large umbrella provides shade, while a tree adds a natural element to the space, creating an inviting area for relaxation.

Guesthouse in Seminole

Beachy Bohemian Bungalow with all the perks!

This cozy spot sits in a quiet neighborhood that boasts access to the Pinellas Trail Bike rental close Full kitchen w/ extras Queen bed w/ built in drawers Shelves & clothing rack Smart TV Full bath w/ walk-in shower Ample outlets/ USB Private deck for sun & shade Beach chairs, towels etc for beach Convenient to a dozen parks, beaches, shopping & restaurants. 2 miles to Madeira Beach 3 m - Johns Pass 1.2 m - Seminole City Center 7.6 m - St. Pete/ Clearwater Airport NO SMOKING NO PETS

4.85 out of 5 average rating, 633 reviews

Florida Island Beauty@theBeach@Heated Pool

My place is close to white sand beaches and has a heated pool. Price is amazing and its fully renovated in the latest fashion with fun beachy accents! You’ll love my place because of the location, the neighborhood, and the outdoors space. My place is good for couples, solo adventurers, a parent and a child. I have adjusted my prices so they are adjusted accordingly with consideration of the area recovering from hurricane Helene from last year. Photos were taken on August 25th, 2025.

Superhost

A cozy sleeping area is presented with a spacious bed, dressed in neutral linens. A light wood frame complements the soft color palette. Wall-mounted light fixtures provide gentle illumination, while a shelf adorned with plants adds a touch of greenery. A small stool is positioned beside the bed.

Tiny home in St. Petersburg

4.87 out of 5 average rating, 141 reviews

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our thoughtfully designed studio—small but full of comfort, efficiency, and charm. If your priority is a cozy bed , a truly clean space and location, look no further. Loved by hundreds of wonderful guests, this is one of two private studios in a tiny house, ideal for solo travelers or couples. You’ll have everything you need, plus access to a beautiful shared gazebo with seating, dining areas, and lush greenery. We have a team of four Superhosts, available to help. 🌴☀️🏖️

The image shows a view of the beach, with smooth, sandy shores leading to a row of modern condo buildings in the background. The condos are designed with balconies, featuring multiple stories and large windows, under a clear blue sky.

4.91 out of 5 average rating, 405 reviews

Indian Shores Gulf Front Rental

Beautiful 2 bed 1 bath luxury condo on the Gulf of Mexico. We are steps from the beach. Unit has partial water view. Beautiful state of the art kitchen and luxurious furnishings. Everything you need for your perfect vacation. Totally non-smoking unit. Come and stay with us. This is a second floor walk up condo. There are 27 steps. May not be suitable for the elderly or small children. Check in 3pm. Check out 10am Our maximum occupancy is 4 people including children.

Apartment 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, 147 reviews

Triplex- heated pool, bikes, walk to beach,

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

4.99 out of 5 average rating, 106 reviews

A silhouette of a person stands on a paddleboard, gliding over shimmering ocean waves. The sun's reflection creates a sparkling pathway on the water, enhancing the serene atmosphere of the coastline.

Guest suite in Seminole

Pesky Pelican Studio 3 miles to Madeira Beach

Relax and recharge in this cozy studio-perfect for 2. This property is located in a friendly, laid-back neighborhood just a 6min drive to Madeira Beach. Easy access to several gulf beaches, bars, restaurants and airports. Spend the day relaxing on the patio or fun in the sun at the beach. Book one of the many adventure tours out of Johns Pass Village and make this a vacation you won’t forget! Tiki Boats/Jet Ski/Parasail. Queen bed, coastal tiled bathroom, kitchenette, patio

Popular amenities for Redington Beach family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 214 reviews

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

Condo in Madeira Beach

Lux Condo w/ 2 balconies, Ocean & Marina views

4.91 out of 5 average rating, 176 reviews

A sunset is captured over the intercoastal waterway, with warm hues reflecting on the water's surface. Silhouettes of palm trees line the foreground, while distant markers indicate the waterway's navigation. The scene conveys a tranquil ambiance, enhanced by the fading light.

Condo in St. Petersburg

Heron's Hideaway- Studio by the bay!

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.

4.94 out of 5 average rating, 130 reviews

Tropical Beachfront Penthouse-Beach Cottages

Home in Indian Rocks Beach

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

5 out of 5 average rating, 179 reviews

Piece of paradise in Indian Rocks Beach.

Houseboat in Madeira Beach

A cozy living area features a gray sectional sofa adorned with cushions, complemented by a round wooden coffee table. Light filters through multiple windows, highlighting the soft blue and neutrals in the decor. A ceiling fan is overhead, and a potted plant adds a touch of greenery.

4.93 out of 5 average rating, 107 reviews

40ft Floating Bungalow with Resort Perks

4.84 out of 5 average rating, 172 reviews

A bright and airy living area features a comfortable couch facing a modern television. A coffee table sits in the center, with a view of the intracoastal waterways visible through large sliding glass doors that lead to the balcony.

Condo in Madeira Beach

Lovely Water View Condo, Top Floor, Steps to Beach

A serene sunset is captured over the calm ocean, with vibrant orange and yellow hues reflecting on the water's surface. Silhouettes of palm fronds frame the view, while a faint outline of the shoreline can be seen in the foreground.

4.98 out of 5 average rating, 146 reviews

The Seascape Premier Beachfront Cottage-Gulf View

4.96 out of 5 average rating, 268 reviews

A private balcony offers a serene view of the bay, framed by lush palm trees. A glass table and two chairs are positioned for easy enjoyment of the surroundings, while the sparkling water glimmers under a clear blue sky.

Condo in St. Petersburg

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!

Family- and pet-friendly home rentals

Tiny home in St. Petersburg

A bright studio space features a comfortable bed with soft linens, flanked by two wooden benches. A small vanity with a mirror and sink is positioned nearby, while warm overhead lights complement natural light streaming in from the window.

4.96 out of 5 average rating, 193 reviews

King Bed Studio | Outdoor Kitchen | Free Parking

Tiny home in St. Petersburg

A cozy sleeping area features a wooden bed with a light-colored comforter. Soft lighting is provided by pendant fixtures on either side. A shelf above the bed displays various plants, adding a touch of greenery to the earthy tones of the room.

4.87 out of 5 average rating, 119 reviews

Charming Studio | Outdoor Kitchen | Free Parking

Apartment in Indian Rocks Beach

The shared resort-style backyard features a large heated pool surrounded by lounge chairs and umbrellas. Lush palm trees provide shade, and a peaceful ambiance is created by the surrounding greenery. The inviting blue sky completes this outdoor relaxation area.

4.94 out of 5 average rating, 142 reviews

New! Starfish Wishes! Heated Pool! Steps to beach!

Cottage in Indian Rocks Beach

A single-story cottage features a pink exterior with large windows allowing natural light. A landscaped garden with decorative stones is visible in the front. White chairs are placed near the entrance, and ample parking spaces are provided in the driveway.

4.9 out of 5 average rating, 317 reviews

Vintage Florida Beach Cottage B

4.93 out of 5 average rating, 103 reviews

An outdoor patio area features a tiled surface surrounded by greenery and a wooden fence. A round table with chairs is positioned next to a gas grill, while a large tree provides shade. Potted plants add a touch of nature to the space.

Tiny home in Gulfport

Avocado Casita 10 mins to Beaches

Superhost

A spacious sleeping area features a large bed with white linens and a textured blue throw. Natural light filters through two windows adorned with light curtains. Decorative elements, including a small vase, add a subtle touch to the room's design.

Guest suite in St. Petersburg

4.82 out of 5 average rating, 371 reviews

Cozy St Pete Suite near beaches

4.96 out of 5 average rating, 233 reviews

A cozy guest suite is shown, featuring a spacious bed against a soft blue wall. A colorful octopus-patterned rug adds charm to the room. Nearby, a coffee station is visible alongside a potted plant, with a well-lit seating area in the background.

Guest suite in Seminole

Beautiful Private entry & yard, non shared space.

Guesthouse in Pinellas Park

A cozy cottage is showcased, featuring a yellow exterior with white shutters. A white picket fence borders the front yard, which is adorned with green grass and shrubs. Two blue chairs are positioned on the porch, inviting relaxation.

4.87 out of 5 average rating, 278 reviews

pet friendly on an equestrian farm

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 140 reviews

An aerial view captures a spacious patio surrounding a custom saltwater pool, where lounge chairs are arranged alongside. Lush landscaping features palm trees and flower beds, while a covered seating area, equipped with outdoor furniture, is visible behind the pool. The home showcases a modern design with a sleek metal roof.

Home in Seminole

Tootsie’s Beachside Retreat-New Heated Pool

A spacious balcony features two chairs and a round table, providing a stunning view of the Gulf. The horizon shows a clear sky above the tranquil water, with sunbathers visible along the beach. Lush greenery and a palm tree are seen framing the scene.

4.92 out of 5 average rating, 145 reviews

"Jewel At The Shores" Gulf Front, sleeps 5

A waterfront view showcases the community pier lined with palm trees, providing access to the Intracoastal waterway. The nearby building features balconies and patio furniture under blue umbrellas, enhancing the leisure atmosphere. Multiple docks extend into the clear water, inviting relaxation.

4.99 out of 5 average rating, 110 reviews

Blue Sea Renity -Steps to Beach| Heated Pool

Cottage in Indian Rocks Beach

An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.

4.96 out of 5 average rating, 165 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Bungalow in Indian Rocks Beach

A private tiki hut features a thatched roof, ambient lighting, and a large television. Seating is provided by several lounge chairs and a unique wicker chair, arranged around a stone floor. Lush greenery surrounds the area, enhancing the outdoor experience.

4.9 out of 5 average rating, 142 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

Superhost

Condo in Belleair Beach

4.82 out of 5 average rating, 104 reviews

Condo On The Beach - Heated Pool - Self Check-in

4.99 out of 5 average rating, 206 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.