Family-friendly holiday rentals in Redington Shores

A spacious backyard is featured, showcasing a heated saltwater pool surrounded by a large paver deck. Lush green grass fills the area, bordered by well-maintained landscaping. Tall trees provide shade in the background, contributing to the serene outdoor environment.

4.98 out of 5 average rating, 127 reviews

JOJO'S Beachside 1Acre Estate-New Pool

LUXURY CUSTOM HOME WITH NEW HEATED SALTWATER POOL ONLY 1.5 MILES TO BEAUTIFUL WHITE SAND REDINGTON BEACH ON 1 ACRE OF LAND. HOME HAS JUST BEEN TOTALLY RENOVATED WITH TASTEFUL FINISHES. THIS AREA IS VERY QUIET AND UNIQUE FOR PINELLAS COUNTY WITH LARGER LOTS AND HOMES. 2300 SQUARE FEET WITH HIGH VAULTED CEILINGS. LARGE OPEN KITCHEN, T.V.'S IN EVERY RROM. GREAT LOCATION JUST MINUTES FROM: COFFEE SHOPS , GROCERY STORE, SHOPPING, RESTAURANTS, MOVIE THEATERS AND PARKS. LARGE PAVER DECK BY POOL AREA.

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Bungalow in Indian Shores

4.96 out of 5 average rating, 197 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

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Apartment in Redington Shores

4.88 out of 5 average rating, 125 reviews

Beach Studio 8

This fully renovated Studio is right on Gulf Blvd and across the street you have the Beach! Great restaurants up and down Gulf Blvd, 30 minutes to St. Petersburg or Clearwater, 45 minutes to Tampa Airport. You have a dedicated parking spot and easy Beach access. Includes: Queen size Bed TV Wifi Fully Equipped Kitchen- Keurig, pots and pans, dishware, silverware, etc. (all brand new) Washer/Dryer in the building (Credit card Payments accepted) Heated Pool in front of your door.

KitchenIndoor spacesParks

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.

4.9 out of 5 average rating, 442 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.

Indoor spacesKitchenSleep quality

A modern living area features a large sectional sofa adorned with decorative pillows. A round coffee table sits at the center, displaying a small plant and snacks. Bright red chairs are positioned near a window, complemented by a light and airy ambiance from natural light.

4.91 out of 5 average rating, 312 reviews

Beachy Home Minutes from sugary sand beaches

Sunny Florida Beach Home! 4 minutes drive to the #1 best beach in America nominated by Trip Advisor, where you will find beautiful white sand and extremely warm and clear water! Enjoy tons of top local restaurants and entertainment all minutes from your door in this relaxing, low key beach neighborhood. Super kid friendly! Games, BBQ, swing set, Apple TV, and bikes for the whole family! Enjoy the entire house that has been completely remodeled and is sparkling CLEAN!

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Apartment in Indian Rocks Beach

4.88 out of 5 average rating, 110 reviews

On private beach! Ground Level Full Kitchen Unit 6

Fully remodeled in 2025! We’re back & better than ever! ON Private Beach with breathtaking Gulf views! This 1 bedroom unit w patio leading to private beach features full kitchen, king bed and sleeper sofa, sleeping 4. Smart TVs, furnished linens, towels, toiletries, beach towels, beach chairs for your use. 1 Free parking space included. For additional availability see IDENTICAL unit same location Tide Vibes #7 and 2 bedroom unit #5, sleeps 6.

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4.81 out of 5 average rating, 387 reviews

Beachside Mini-Condo w/ Pool on Redington Beach!

NOTE: If your dates aren't available, we have several other beach listings varying in size, including some not advertised here. See my profile for availability and ask for details! Nestled in the heart of the #1 rated beach area in the U.S., this is one of the only boutique vacation complexes located ON THE BEACH! Experience relaxing beach life, steps from your door to the iconic white sands. Nearby, countless attractions await!

Indoor spacesFamilyWalkability

The image shows a heated pool surrounded by a patio area with lounge chairs. Palm trees provide shade, and the two-story building encircling the pool features balconies. Well-maintained landscaping adds greenery to the setting, creating a peaceful atmosphere.

4.86 out of 5 average rating, 202 reviews

Royal Orleans at Redington Beach ( Studio 203 )

Royal Orleans 203 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

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Villa in Redington Shores

4.92 out of 5 average rating, 166 reviews

Almost beachfront, 1 house to beach! 2 King 2 twin

Just a 1-minute walk to a gorgeous Gulf beach with breathtaking sunsets and miles of white sand! Walk to restaurants, then relax in this peaceful, hidden gem tucked away from busy condo crowds. One of only 3 units in a charming Gulf-side villa. Includes beach chairs, towels, cooler, washer/dryer, Wi-Fi, free parking, central A/C, and nearby pickleball. Sleeps 6 with 2 king bedrooms and 1 bedroom with 2 twins.

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Apartment in Redington Shores

4.89 out of 5 average rating, 36 reviews

Cottage #2| 2 bedroom Charming & Cozy|Dogs OK

Welcome to our charming 2-bedroom Misty Beach Cottage—just steps from the sand! Enjoy breathtaking sunsets and the peaceful rhythm of the waves. Inside, you’ll find an open living, kitchen, and dining area filled with natural light. Step outside and you’re on the beach—perfect for morning walks, dolphin watching, or relaxing with your toes in the water. Your coastal escape awaits—book your stay today!

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Cottage in Redington Shores

An expansive view of a sandy beach stretches under a clear blue sky. Soft dunes with tall grass line the shore, while gentle waves can be seen lapping at the sand, creating a serene coastal atmosphere.

4.87 out of 5 average rating, 31 reviews

2BR Charming Beach House Steps To The Beach 2nd FL

Escape to our quaint, peaceful 2-bedroom island-style home with direct beach access! This cozy retreat is your perfect home away from home, offering a relaxing getaway just steps from the sand and vibrant sunsets. Ideal for those who appreciate simple living and the beauty of the coast. Comfortably accommodates up to 4 guests.

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Home in Indian Rocks Beach

4.92 out of 5 average rating, 130 reviews

Beach House | Heated Pool & Spa | Golf Cart

Newly renovated beach house just 2 blocks from IRB with a HEATED saltwater pool, spa, tanning deck, and 4‑passenger golf cart. Pet‑friendly and set in a quiet, safe neighborhood, this cozy 2‑bed retreat is perfect for couples and small families seeking comfort, convenience, and unforgettable Gulf Coast memories. BTR# 2041

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Popular amenities for Redington Shores family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 162 reviews

The Seascape Premier Beachfront Cottage-Gulf View

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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, 139 reviews

Tropical Beachfront Penthouse-Beach Cottages

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An aerial view of a modern two-story home surrounded by lush greenery and palm trees, with a backdrop of tranquil water. The property's landscaping features a paved driveway leading to the entrance, while nearby boats are docked along the shoreline.

4.94 out of 5 average rating, 338 reviews

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms

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Condo in North Redington Beach

A serene beachfront view is captured under a clear blue sky. The vivid turquoise water reflects sunlight, creating a shimmering pathway across the calm sea. Gentle waves roll onto the soft sandy shore, where a person is seen walking along the beach.

4.91 out of 5 average rating, 127 reviews

Toes in the Sand Beachfront penthouse condo

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Home in Indian Rocks Beach

An inviting outdoor space features a heated saltwater pool and spa surrounded by sun loungers. A dining area is visible next to the pool, with a backdrop of palm trees and a screened lanai. The bright sky enhances the relaxing atmosphere.

5.0 out of 5 average rating, 109 reviews

Sandy Morning Restored | Pool Spa

Indoor spacesFamilyAccess

4.83 out of 5 average rating, 157 reviews

The Flamingo Oasis | Bowling, Heated Pool, Hot Tub

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A covered balcony features a glass-top dining table accompanied by four wicker chairs. The expansive view overlooks the tranquil Gulf of Mexico, with gentle waves breaking on the sandy shore. The sky is overcast, providing a serene backdrop to the coastal scenery.

4.8 out of 5 average rating, 123 reviews

Amazing Beachfront corner unit with two balconies!

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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.

4.99 out of 5 average rating, 199 reviews

Piece of paradise in Indian Rocks Beach.

Indoor spacesKitchenWi-Fi

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 109 reviews

Backyard Oasis! Fully remodelled! 4 min to beach!

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Bungalow in Redington Beach

4.93 out of 5 average rating, 267 reviews

Single Family Home One Level ~ Walk to the Beach!

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4.98 out of 5 average rating, 186 reviews

Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

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Bungalow in Indian Shores

An aerial view showcases a cluster of charming two-story homes nestled near the beach. The golden hues of the sunset reflect off the water, while the sandy shore and gentle waves create a serene coastal atmosphere.

5.0 out of 5 average rating, 247 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

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Townhouse in Indian Rocks Beach

The two-story condo building features a light-colored exterior, spacious balconies, and palm trees lining the entrance. The proximity to the sandy beach and vibrant blue Gulf water is visible in the background, showcasing a serene coastal atmosphere.

4.96 out of 5 average rating, 160 reviews

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U3 ♥

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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.

4.97 out of 5 average rating, 195 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

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Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

4.97 out of 5 average rating, 231 reviews

Your private Waterfront Pool home!

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4.93 out of 5 average rating, 163 reviews

Home in Largo

Swim-Out Bedrooms, Waterfall pool, Peace Place

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Family-friendly home rentals with a pool

4.94 out of 5 average rating, 161 reviews

Quiet, Beachy Poolside Studio/1 Min Walk to Beach

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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.

4.81 out of 5 average rating, 268 reviews

Beautiful Studio on the paradise white sand beach!

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4.94 out of 5 average rating, 125 reviews

🍍Beautiful Home Heated POOL 5min to BEACH. 8 ppl🍍

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4.85 out of 5 average rating, 678 reviews

Florida Island Beauty@theBeach@Heated Pool

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Bungalow in Indian Rocks Beach

A pool area is surrounded by vibrant tropical landscaping, featuring lounge chairs arranged around a circular pool. Soft lighting illuminates the scene, enhancing the greenery. In the background, a pink float adds a playful touch to the inviting ambiance of the outdoor space.

4.93 out of 5 average rating, 177 reviews

Neptune's Nest | Amazing Htd Pool | Steps to Beach

Indoor spacesKitchenQuiet

4.92 out of 5 average rating, 93 reviews

Peaceful Poolside Studio - Across from Beach

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A panoramic view of a serene beach is presented, featuring soft white sand and gentle waves. Colorful umbrellas and beach chairs are scattered along the shore, with a few beachgoers enjoying the tranquil ocean. The clear blue sky reflects the calm atmosphere of the seaside.

5.0 out of 5 average rating, 36 reviews

Oceanfront Condo Corner Unit2BR/2BA Great Location

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A bright living area features large windows offering sweeping ocean views. A sleek white sectional sofa sits atop a soft area rug, accompanied by a stylish coffee table set with glasses and a bottle. A flat-screen television is mounted above an electric fireplace, adding comfort to the space.