Holiday rentals with a pool in Johns Pass

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.

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Superhost

An open living and dining area features a wooden dining table with six chairs, complemented by a pendant light. A comfortable seating arrangement includes a dark sofa and armchair. Floor-to-ceiling glass doors offer views of the ocean, enhancing natural light in the space.

4.85 out of 5 average rating, 110 reviews

Modern Oceanview Heated pool overlooking Mad Beach

*Heated Pool! Winter Special* Create your dream vacation from our gulf-front home with side ocean views overlooking Florida's beautiful Madeira Beach. This 2 bedroom, 2 bath condo has an open layout with all modern amenities and extras. With balcony access from both the living room and the large master bedroom, you can sip your morning coffee on the deck enjoying the refreshing salty air of the gulf breeze as you plan your next adventure. Spacious, fully-stocked kitchen, plenty of room to enjoy!

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4.9 out of 5 average rating, 129 reviews

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.

Flat in Madeira Beach

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

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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!

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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.

40ft Floating Bungalow with Resort Perks

Unmatched Scenic Serenity: Imagine waking up to stunning sunrises and gentle ocean breezes. Your houseboat becomes a floating oasis, providing the comforts of a hotel but floating. Exclusive access to the resort across the street on the beach. Where you can use the heated pool and hot tub. Outdoor grilling area with corn hole boards are available to entertain you while you cook at the Beach Resort. No Grill on the Boat. *Boat is stationary at dock. **MOTION SICKNESS?? PLEASE DO NOT BOOK**

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4.92 out of 5 average rating, 169 reviews

Apartment in Treasure Island

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.

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.

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4.99 out of 5 average rating, 231 reviews

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.

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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!

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4.92 out of 5 average rating, 103 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.

Flat in Madeira Beach

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.

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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 !

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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.