Waterfront vacation rentals in Madeira Beach

An aerial view captures the beachfront landscape, highlighting an inviting shoreline bordered by a mix of residential and commercial properties. The water showcases varying shades of blue, while the sandy beach stretches invitingly. Identifiable structures are situated near the coast, establishing a vibrant neighborhood.

4.88 out of 5 average rating, 130 reviews

MadeiraC2 Waterfront & 2-3 minutes Walktothe Beach

Maderia Beach WATERFRONT & 2-3 minutes' walk to the beach. A great LOCIATION! A short drive from John's Pass Boardwalk & Johns' Pass Village. Feel the breeze, relaxing & enjoy the fishing on the docks right at our back yard! Everything you need, including 2 beds (1 Queen bed in bedroom & 1 twin sofa bed), well-equipped kitchen, parking permit, WIFI, Roku TVs, beach towels & chairs, umbrella. Restaurants, bars, shopping, Dolphin tours, fishing tours, boat & ski rentals ...are in walking distance.

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.

4.99 out of 5 average rating, 214 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

4.98 out of 5 average rating, 172 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

4.86 out of 5 average rating, 156 reviews

The single-family beach cottage features a light yellow exterior with red accents and three prominent windows. Surrounding the home, palm trees and landscaping provide a lush atmosphere. A paved area holds several designated parking spaces in front of the cottage, with a stone picnic table nearby.

Cottage in Madeira Beach

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

A vibrant blue bungalow is surrounded by lush green palm trees and colorful plants. A well-maintained lawn features a stone pathway leading to the entrance, with a covered porch visible. The bright blue exterior creates a welcoming appearance against the clear blue sky.

4.93 out of 5 average rating, 109 reviews

#1 -Sea Turtle Bungalows @John's Pass 1B/1B

Our cozy Bungalow is for 2 to 4 ppl, and provides you with everything you need to enjoy your visit. In the bedroom is a King size bed and a spa styled bathroom. The living space has a sofa that converts into a queen size bed and a 55” Smart HDTV. The kitchen is fully equipped with new SS appliances, a Keriug coffee maker and comp. coffee. This unit has a personal patio for relaxing and is located in the heart of John’s Pass, steps from the boardwalk/village and a short walk to the beach.

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.

4.9 out of 5 average rating, 189 reviews

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.

An aerial view showcases a vibrant coastal landscape, featuring a marina filled with boats. The sandy beach extends alongside the tranquil blue waters of the Gulf of Mexico, bordered by colorful buildings. The road leads to the beach, highlighting the proximity to waterfront activities.

4.97 out of 5 average rating, 167 reviews

Penthouse Water View, Pool, @ Johns Pass!

Penthouse corner unit with stunning water view from the living room, bedrooms and balcony! This waterfront condo is in prime location. A block away from Johns Pass Boardwalk (#1 tourist destination in the county) and RIGHT across from the pristine white sands & sunsets of the Gulf of Mexico. The property offers a heated pool, hot tub, fitness room & event center. Our condo has everything you need including fully stocked kitchen, laundry in unit, high speed wifi & beach equipment.

A tranquil view captures the sandy shoreline meeting the calm waters of the Gulf, with gentle waves lapping at the beach. Lush palm trees are positioned in the foreground, while a small blue trash bin is nestled among the greenery. The sky features soft clouds, hinting at the day's potential.

4.97 out of 5 average rating, 144 reviews

Beach Front Penthouse Riley's Retreat Island Inn

800 sq ft top floor condo with spectacular views of the Gulf of Mexico, Boca Ciega Bay, and the City. Located in the iconic Island Inn Beach Resort; step out of the lobby and onto the sand! Florida sunrises and sunsets are legendary, and you can enjoy both from your private top floor balcony. We offer one of the finest condo's in the building with the unique ability to enjoy North, South, East, and West vistas. This condo is unlike any other unit in the building--a must see!

Townhouse in Madeira Beach

A rooftop terrace is presented with modern outdoor furniture, including two sofas, two chairs, and a coffee table. The space offers panoramic views of the intercoastal waters and surrounding area, with a clear sky and scattered clouds visible above.

4.93 out of 5 average rating, 120 reviews

Luxury Home N/Heated Pool/Rooftop/Steps to Beach

New, 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms/modern townhome with heated salt water POOL located near a canal and the gulf just two blocks from the beach. Please note the pool is shared with the other side of the duplex. You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to the beach, restaurants, and volleyball. Close to Johns Pass, 2 miles. Please ask for the golf cart availability and a fee.

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.

4.99 out of 5 average rating, 218 reviews

Lux Condo w/ 2 balconies, Ocean & Marina views

This luxury condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.

A spacious wooden dock extends over calm waters, flanked by moored boats under a clear blue sky. The dock features sturdy railings and provides an inviting access point to the waterfront scenery.

4.85 out of 5 average rating, 260 reviews

Amazing water front view home newly renovated

Don't miss the amazing waterfront sunset from the deck. This 1900 sq ft newly renovated,3 bdrm 2 bth home is 10 minutes walk to the beach or park at the beach parking. Sleeps 10, 1 king bd, 2 queen bds, 2 queen pull outs, 6 parking spaces, large deck, dock available for guests, patio furniture, gas grill, much more. Close to shopping, restaurants, and entertainment. Fly in through Tampa international airport and Saint Petersburg airport. Business tax BT# 1701

4.99 out of 5 average rating, 103 reviews

Beach Front Madeira Beach

Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

Popular amenities for Madeira Beach waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.96 out of 5 average rating, 117 reviews

“Beach Walk Retreat • Free Parking

A direct view of the Gulf shoreline is visible from the balcony, showcasing a sandy beach with beach chairs and umbrellas. A private pool is located below, surrounded by a patio area with several lounge chairs, creating an inviting setting for relaxation.

4.9 out of 5 average rating, 109 reviews

Welcome to Gulf-Front Paradise!

Apartment in Treasure Island

A clean swimming pool is positioned alongside a waterfront, framed by a white fence. Sun loungers are neatly arranged on a deck, with palm trees and a dock visible in the background. The sky features soft clouds and clear blue tones, creating a serene outdoor setting.

4.9 out of 5 average rating, 276 reviews

Beach & Bay 1 Bdrm Condo Boat/Fish Dock with Patio

Apartment in Treasure Island

4.84 out of 5 average rating, 127 reviews

Complete Renovation-everything new! Amazing views

Apartment in Indian Shores

The living area features a spacious couch and a flat-screen television, with a soft area rug anchoring the space. Floor-to-ceiling sliding glass doors provide sweeping ocean views and direct access to the private balcony, creating an inviting connection to the beach.

4.92 out of 5 average rating, 144 reviews

Ocean Front Condo!

Apartment in Independence Square

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

4.96 out of 5 average rating, 183 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

A comfortable seating area features a woven hanging chair, positioned on a balcony overlooking the ocean. The view reveals a sandy beach and calm waters, extending to the horizon under a clear blue sky.

4.91 out of 5 average rating, 76 reviews

Oceanfront Luxury paradise

Apartment in Treasure Island

An inviting studio interior is shown with light-coloured walls and a modern kitchenette visible in the background. A doorway leads to a bathroom featuring tropical-themed wallpaper. A small dining table and chair are positioned in front of a cozy seating area with a dark sofa.

4.99 out of 5 average rating, 140 reviews

Popular Beachside Studio w Relaxing Patio & Palms!

Waterfront house rentals

4.88 out of 5 average rating, 155 reviews

Azule|Waterfront | Walk to Beach-Dock-Bikes-Kayaks

4.95 out of 5 average rating, 117 reviews

Home in Madeira Beach

Boardwalk Bungalow - Johns Pass & beach steps away

4.94 out of 5 average rating, 324 reviews

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.

Home in Seminole

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms

5 out of 5 average rating, 100 reviews

Waterfront Duplex: 3 Blocks to Beach, Hot Tub, SUP

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, 188 reviews

Piece of paradise in Indian Rocks Beach.

Superhost

The outdoor pool, surrounded by palm trees, reflects the clear blue sky. Comfortable loungers are placed nearby, offering ample space for relaxation. The glistening water leads to views of the waterfront, enhancing the serene atmosphere of the outdoor environment.

4.83 out of 5 average rating, 362 reviews

Stunning views! Spot dolphins from the pool!

Superhost

Home in Redington Beach

5 out of 5 average rating, 4 reviews

Redington Beach near beach on ICW w/pool & dock

4.94 out of 5 average rating, 35 reviews

Home in Madeira Beach

Sun-drenched Townhome on beautiful Madeira Beach!

Waterfront condo rentals

A bright bedroom features a spacious bed adorned with light blue and white striped linens. Natural light floods the room through sliding glass doors that lead to a private balcony with an ocean view. Two decorative lamps and a textured area rug enhance the serene atmosphere.

4.91 out of 5 average rating, 143 reviews

Summer Penthouse, Private Balcony, Beach View #602

The aerial view displays a modern four-story condo building with a mix of orange and white façades. Balconies extend from each level, and a marina with boats is visible at the base, along with beach access in the background.

4.82 out of 5 average rating, 114 reviews

Steps to beach with Marina Sunsets – 3 -Bed condo

A well-lit living area features a round dining table surrounded by four white chairs. A comfortable sofa and armchair are positioned near large windows, offering views of the outdoors. Light-colored walls and soft furnishings enhance the bright, airy ambiance.

4.9 out of 5 average rating, 131 reviews

2/2 Newly remodeled Beach Front - Sunset Vistas

4.98 out of 5 average rating, 284 reviews

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

Condo in St. Petersburg

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

4.9 out of 5 average rating, 421 reviews

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.

Condo in Indian Shores

Indian Shores Gulf Front Rental

4.98 out of 5 average rating, 150 reviews

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.

Condo in Indian Shores

The Seascape Premier Beachfront Cottage-Gulf View

An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.

4.98 out of 5 average rating, 153 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Aerial view of a two-story condo building located beside a swimming pool, surrounded by palm trees. The pristine beach and the Gulf of Mexico are visible in the background, showcasing calm waters and distant beachgoers.