Waterfront vacation rentals in Madeira Beach

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, 243 reviews

Rincón Divino MB 2 Balconies, Ocean & Marina Views

EXCLUSIVE: Saturday checkout is at 5pm. This 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.

4.95 out of 5 average rating, 112 reviews

Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

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, 129 reviews

Million Dollar Gulf-Front View!

This Gorgeous 1st floor, Direct Gulf-Front condo is located on the South end of beautiful Madeira Beach, directly across the street from World Famous John's Pass Village & Boardwalk. Enjoy this 1/1 + premium queen pull-out sleeper sofa with full-sized kitchen, private heated Pool, Outdoor Grills w/ Tiki Huts on one of the Top 10 Beaches in the US. Best Attractions: Dining, Shopping, Boating, Fishing, Dolphin tours, Jet skiing, Paragliding - ALL w/in Walking Distance! Free covered parking GND FL

A modern living area features a circular dining table set for four, complemented by plush armchairs and a sofa. Large windows allow natural light to fill the room, adorned with light-colored curtains. A television is mounted on one wall, alongside decorative elements including a palm plant.

4.99 out of 5 average rating, 101 reviews

Steps to Johns Pass+Beach | Water View | Htd. Pool

Welcome to Madeira Bay, your cozy home away from home in Madeira Beach, FL. Located directly across the street from the beach & just 1 block north of John's Pass Village, this modern newly built 2 bed 2 bath private waterfront condo offers the perfect beach getaway for guests & families alike. Featuring stunning sunrise views over the intracoastal & in walking distance to restaurants, shopping, parasailing, boating, jet ski rentals, bike rentals, & more. We know you'll love your stay with us!

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, 231 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.

Aerial view of a beachfront building located near Madeira Beach, showcasing proximity to the ocean and nearby establishments. The scene includes colorful structures along the coast, palm trees lining the street, and a clear blue sky reflecting sunlight over the water.

4.93 out of 5 average rating, 114 reviews

Beachfront building across from Johns Pass Village

Beachfront building - head downstairs to enjoy the white sand beaches of Madeira Beach! Partial beach view from the large balcony. Updated 2-bedroom condo with contemporary furniture. Prepare meals in the fully equipped kitchen or walk across the street to John's Pass Village & Boardwalk with many restaurants, retail stores, ice cream shops, sunset cruises, jet ski rentals and more! Condo offers walkability and beach access downstairs. Price is discounted - pool is closed until January 2027.

4.88 out of 5 average rating, 177 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!

Bungalow in Indian Shores

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

4.97 out of 5 average rating, 206 reviews

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.

4.92 out of 5 average rating, 104 reviews

Oceanfront Luxury paradise

Oceanfront Paradise, Resort with brand new heated pool and spa opened in 4/1/2025 , unobstructed ocean views from your balcony and bedroom, magical sunset with jumping dolphins, direct beach access, Condo renovated with Malibu / Nobu style natural wood tones, Master bedroom spacious private retreat with oceanfront views, walk-in closet , en-suite Luxury master bath with Marble floors, Kitchen remodeled fully equipped with all utensils/new appliances, renovated Guest bath , washer /dryer.

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.

4.84 out of 5 average rating, 131 reviews

Steps to beach with Marina Sunsets – 3 -Bed condo

Steps from Madeira Beach! Enjoy this spacious 3-bedroom , 2-bath newer condo with beautiful marina views, a private balcony, and room for 6 ! 1 min walk to John’s Pass for dining, shopping, fishing, and entertainment. Includes free Wi-Fi, 3 Smart TVs, a full kitchen, washer/dryer in unit , and free parking for one car —everything you need for a relaxing Florida vacation! Watch the boats in the marina while having your morning coffee ! We look forward to hosting you !

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, 185 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.

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

4.86 out of 5 average rating, 674 reviews

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

Popular amenities for Madeira Beach waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Indian Shores

A spacious living area is furnished with two comfortable leather sofas and a wooden side table. A large flat-screen TV is positioned nearby. Natural light floods the room through expansive glass doors leading to a balcony, with ocean views visible in the distance.

Direct Beachfront Condo, Ocean balcony view!

4.93 out of 5 average rating, 230 reviews

4.95 out of 5 average rating, 147 reviews

“Beach Walk Retreat • Free Parking

Apartment in St. Petersburg

Waterfront studio! Heated pool and hottub

4.95 out of 5 average rating, 150 reviews

4.79 out of 5 average rating, 164 reviews

Bay & Blvd | Steps to Beach, Pool & John's Pass

Apartment in Treasure Island

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

4.9 out of 5 average rating, 290 reviews

Apartment in Treasure Island

An inviting living area features a light gray sofa and a round white coffee table. Large glass doors open to a private balcony with unobstructed views of the Gulf of Mexico, creating a seamless connection with the beachfront landscape.

Beachfront Condo w/ Ocean View - Newly Renovated!

4.94 out of 5 average rating, 197 reviews

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.

4.91 out of 5 average rating, 120 reviews

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

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, 146 reviews

MadeiraC2 Waterfront & 2-3 minutes Walktothe Beach

Waterfront house rentals

4.95 out of 5 average rating, 126 reviews

Home in Madeira Beach

Boardwalk Bungalow - Johns Pass & beach steps away

Home in Indian Rocks Beach

A spacious living area features a large sectional sofa, complemented by decorative tables and potted plants. Expansive windows provide views of the water and outdoor seating, while natural light brightens the modern, open layout.

Walk to Beach! Waterfront Lux Retreat w/Kayaks

5.0 out of 5 average rating, 100 reviews

Home in Indian Rocks Beach

Ocean Dreaming: Waterfront Home with Heated Pool,

4.97 out of 5 average rating, 145 reviews

4.94 out of 5 average rating, 340 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

Home in Indian Rocks Beach

Waterfront house w/ dock, Walk to Beach, Dogs OK!

4.91 out of 5 average rating, 106 reviews

4.8 out of 5 average rating, 5 reviews

Home in Madeira Beach

Beach House Experience! Classic, Unique, Comfort.

4.86 out of 5 average rating, 22 reviews

Home in Madeira Beach

Beachfront Getaway with Resort-Style Pool

5.0 out of 5 average rating, 29 reviews

Home in Treasure Island

Waterfront Condo with Boat Slip & Fishing Dock

Waterfront condo rentals

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.

4.9 out of 5 average rating, 119 reviews

Luxury Seashell Oceanfront Condo with Pool

5.0 out of 5 average rating, 102 reviews

Condo in Sunset Beach

Glorious Sunsets - Beachfront 2BR Condo

A vibrant sunset casts warm orange and yellow hues across the sky, reflecting on the tranquil Gulf waters. Silhouetted palm trees frame the scene, enhancing the coastal ambiance. The horizon showcases the sun gradually setting, providing a serene view for relaxation.

4.87 out of 5 average rating, 111 reviews

Special 11/07-14/26-All Room Direct Beach Front

A spacious balcony overlooks the ocean, featuring two wicker chairs and a small blue table. The view includes sandy beach and distant waves under a bright sky, creating a serene atmosphere ideal for relaxation.

4.93 out of 5 average rating, 163 reviews

Beachfront 2/2 Condo, Treasure Island,305W Oceana

5.0 out of 5 average rating, 6 reviews

Villa Madeira 604 Luxury Gulf Beachfront Getaway

4.92 out of 5 average rating, 60 reviews

Waterfront Escape - Steps to Beach + John's Pass

A modern kitchen is presented, featuring white cabinetry and light countertops. Equipped with a stove, oven, refrigerator, and dishwasher, it offers essential appliances. Bright pendant lights hang above the island, enhancing the open layout that connects to the living area visible in the background.

5.0 out of 5 average rating, 49 reviews

Newly Renovated Condo with Pool