Pet-friendly holiday rentals in Madeira Beach

4.91 out of 5 average rating, 162 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!

4.92 out of 5 average rating, 166 reviews

The living area features a comfortable seating arrangement with two blue armchairs and a sofa, complemented by a ceiling fan. A dining table for six is visible, along with large glass doors providing a view of the balcony and outdoor scenery.

Condo in Madeira Beach

Penthouse Water View, Steps to Sandy Beach

Breathtaking water views as far as the eye can see! You will take in colorful skies at Sunset with a view that reaches to downtown St. Pete. This top floor 2 bedroom 2 bath condo is beautifully decorated and equipped with everything you will need for your beach vacay. Beach access is directly across the street and you are a block from John's Pass Boardwalk. A heated pool with sun deck, hot tub, gym, covered parking space in the garage for 1 vehicle. Beach towels, chairs, umbrella and a buggy!

4.99 out of 5 average rating, 143 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

4.97 out of 5 average rating, 174 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

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, 189 reviews

King Bed 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. 🌴☀️🏖️

Tiny home in St. Petersburg

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.

4.87 out of 5 average rating, 140 reviews

Charming 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.

4.86 out of 5 average rating, 116 reviews

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our tiny but thoughtfully designed studio—small in size yet big on comfort, care, and cleanliness. Each space is lovingly maintained by my mother, ensuring an extra spotless stay. Perfect for solo travelers or couples, you’ll enjoy a cozy bed, efficient design, and unbeatable value. Step outside to our lush shared gazebo with seating, dining areas, BBQ, and outdoor kitchen appliances—a favorite gathering spot for guests. Superhost team of four always here to help. 🌴☀️🏖️

4.89 out of 5 average rating, 155 reviews

The modern condominium complex features multiple balconies overlooking a pool area. Vibrant tropical plants surround the pool deck, which is equipped with lounge chairs and shaded umbrellas. Clear blue skies and palm trees add to the inviting outdoor space.

Condo in Treasure Island

Beachfront Condo Resort on Treasure Island

Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

4.72 out of 5 average rating, 344 reviews

The open living area showcases a mix of light and neutral tones, featuring a spacious cream-colored sofa with an accompanying ottoman. A dining table with multiple chairs is positioned nearby, while large windows allow natural light to fill the space, highlighting the modern flooring.

Home in Madeira Beach

Beach Side STEPS TO BEACH!

Cozy 2nd flr unit of beach duplex. No busy street to cross to access the beach. 30 steps to 132nd st. public access to sugar sand beaches and crystal blue waters of Gulf of Mexico. Walk 1 block to over 100 merchants including many restaurants, fishing tours, and more! There is a king, queen. full size and sofa bed. Full kitchen with granite countertops and stainless steel appliances. Outdoor shower and deck area. Security cameras are in the front and back of the property.

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 out of 5 average rating, 221 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

Cottage in Indian Rocks Beach

The porch features a circular daybed with decorative cushions, accompanied by a small table and two chairs. Direct views of the bright blue sky and nearby palm trees are visible, enhancing the outdoor relaxation space.

4.97 out of 5 average rating, 160 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292

4.91 out of 5 average rating, 173 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!

Newly remodeled studio with luxury in mind! Keep it simple at this peaceful and centrally-located condo on the bay! Heron's Hideaway is located on the 3rd floor with unobstructed views of the intercoastal waterway! Views of the marina, boats, dolphins and incredible sunsets! This cozy studio is packed with everything you need to enjoy paradise!

Popular amenities for Madeira Beach pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 140 reviews

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

Home in St. Petersburg

Hibernate in our Bear Creek Home

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

4.96 out of 5 average rating, 126 reviews

The exterior of the home features a sandy-colored facade with a bright blue front door. Lush greenery surrounds the property, including trees and shrubs. The fenced yard offers a sense of privacy, and a clear blue sky serves as the backdrop.

Home in Seminole

Beach 5-Min (Near Tampa & Clearwater)

4.87 out of 5 average rating, 119 reviews

A spacious living area features a large sectional couch positioned around a low coffee table. A wall-mounted TV displays a scenic image, while natural light enters through glass doors that open to an outdoor space with a ping pong table.

Home in Seminole

Sky Shower | Ping Pong | King Beds

4.98 out of 5 average rating, 142 reviews

A spacious living area features a sectional couch and a decorative area rug, enhancing the inviting ambiance. A dining table with modern chairs is positioned against a striking patterned accent wall, while natural light filters through the nearby windows, casting a warm glow over the space.

Home in Pinellas Park

Insta Worthy Retreat -Arcade Games- Htd Pool- Golf

Home in Indian Rocks Beach

A private heated pool is surrounded by a spacious deck featuring lounge chairs and a dining area. Palm trees provide shade while boats are visible at the dock. String lights overhead create a relaxed ambiance, and the tranquil water reflects the blue sky.

4.96 out of 5 average rating, 125 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

4.98 out of 5 average rating, 163 reviews

A screened-in pool area features a uniquely shaped pool with clear blue water, inviting relaxation. Sunlight filters through the mesh covering, illuminating the surrounding patio. Lush greenery lines the background, enhancing the outdoor ambiance.

Home in St. Petersburg

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

4.95 out of 5 average rating, 118 reviews

An inviting outdoor space features a heated pool and a shaded area adorned with cafe lights. Two hanging egg chairs and comfortable seating arrangements complement the modern wooden furniture. The stylish striped rug enhances the atmosphere, while the pool's tranquil blue water is visible in the background.

Home in Largo

Palm Paradise - Family Amenities+Central Location

Pet-friendly home rentals with a pool

4.82 out of 5 average rating, 132 reviews

Condo in St. Petersburg

Breathtaking Waterview Condo!

Cottage in Indian Rocks Beach

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

4.99 out of 5 average rating, 192 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Apartment in Madeira Beach

5 out of 5 average rating, 11 reviews

Gulf View Penthouse | Steps to Beach + Johns Pass

Guesthouse in St. Petersburg

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.9 out of 5 average rating, 139 reviews

St Pete Casita Studio with Salt Water Pool & Yard

Condo in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 397 reviews

Amazing views on beachfront

Apartment in St. Petersburg

A private balcony overlooks tranquil waterfront views, featuring a round table surrounded by white wicker chairs. Lush greenery and palm trees frame the scene, while sunlight casts gentle shadows across the space, enhancing the connection to the serene outdoor environment.

5 out of 5 average rating, 19 reviews

Dolphin Views and Resort Pool!

4.85 out of 5 average rating, 74 reviews

A modern kitchen area features a large island with seating, complemented by white cabinetry and gleaming countertops. Natural light floods the space through expansive sliding glass doors, which lead to a private terrace with ocean views. A comfortable seating area is arranged nearby.

Condo in Treasure Island

Luxury Seashell Oceanfront Condo with Pool

4.86 out of 5 average rating, 85 reviews

A serene swimming pool is bordered by palm trees, with lounge chairs positioned around the edge. The pool area is complemented by views of the water and lush greenery, creating a tranquil outdoor escape.

Condo in St. Petersburg

Sunny St. Pete Getaway with Dolphins

Private, pet-friendly home rentals

5 out of 5 average rating, 46 reviews

The image showcases a serene beach scene framed by lush green trees. Soft sand meets gentle waves under a bright blue sky. Vibrant coastal vegetation leads to the sandy shoreline, where silhouettes of beachgoers can be seen in the distance, enjoying the tranquil setting.

Condo in Indian Shores

Stylish Beachfront Condo, Stunning Views

Apartment in Madeira Beach

4.98 out of 5 average rating, 55 reviews

“Madeira Beach Retreat • Quick Walk to Ocean”

Apartment in Treasure Island

The open-concept living area features modern furnishings in soft tones. A spacious sofa and coffee table are positioned around a flat-screen TV. The fully-equipped kitchen, visible in the background, includes stainless steel appliances and a dining table for four. Natural light floods the space through large windows.

4.88 out of 5 average rating, 50 reviews

Spectacular Beachside Gem Steps from the Sand

5 out of 5 average rating, 10 reviews

An inviting living area features a blue sectional sofa and light wood accent chairs. A coffee table rests on a circular area rug. Soft lighting from a floor lamp complements the natural light coming through nearby windows. Decorative wall art enhances the space's coastal charm.

Home in St. Petersburg

Casita near Madeira Beach

4.92 out of 5 average rating, 39 reviews

A charming pink bungalow is set amidst lush tropical landscaping. Green palm trees frame the property, while a white railing surrounds a spacious front porch with steps leading up. Bright sunlight illuminates the exterior, highlighting the inviting entrance.

Home in Treasure Island

Sunshine Beach Bungalow That Is a Unique Treasure

5 out of 5 average rating, 25 reviews

A serene waterfront view is captured at sunset, reflecting vibrant colors on the calm water. Boat docks line the banks, surrounded by lush greenery and palm trees. The peaceful atmosphere is enhanced by distant sailboats gently bobbing in the marina.

Home in Madeira Beach

Flamingo Flair & Waterfront Air — Pure Paradise!

Home in Independence Square

A sunlit sunroom opens to a private deck overlooking the water. Bright blue outdoor chairs are positioned on the deck. Textured walls are complemented by a lamp and potted plant, creating a coastal vibe, while a sign labeled 'BEACH' is displayed above the doorway.

5 out of 5 average rating, 25 reviews

Playa Vista Villa