Vacation rentals with a pool 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, 239 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.

4.94 out of 5 average rating, 176 reviews

Stunning Views Beach Front Condo

Beautifully updated 4th floor 3 bedroom beach front condo! Enjoy gorgeous views of the Gulf of Mexico from a large screened in balcony! Gulf view from both the living room and master bedroom. A large updated kitchen is perfect for the whole family. This condo sleeps 6 comfortably. Cable and WIFI are available as well as beach necessities. A view of the Bay from the front door. Walking distance to John’s Pass. Due to the hurricane, there is still minor repairs being done around the building/town.

A comfortable living area features a round dining table set for four, surrounded by modern chairs. Two seating areas include plush armchairs and a sofa, complemented by a tropical plant. Large windows offer natural light and views of the outdoor scenery.

4.97 out of 5 average rating, 102 reviews

Penthouse Condo on Water Steps to Beach+Johns Pass

Escape to paradise at our gorgeous, 7th floor waterfront condo in the new Madeira Bay Resort in Madeira Beach. Perfectly located directly across the street from the beach, situated on a gorgeous waterfront marina, & just 1 block from John's Pass Village & Boardwalk, enjoy shopping, dining, bars, water sports, boat/bike rentals & more all in walking distance! Newly furnished & well-stocked w/all the comforts of home, enjoy stunning views of the sunrise, intracoastal waterways, & downtown skyline.

4.79 out of 5 average rating, 161 reviews

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

Sun-soaked days & evening sunset skies, warm Gulf water & sugar-white sand right outside your door — welcome to Madeira Beach, one of America's most celebrated family beach destinations. This bright coastal condo puts you steps from the beach & a short walk to Johns Pass Village & Boardwalk. Heated pool, hot tub, fitness center, parking & beach gear all included — no hidden extras. Perfect for families, couples & friend groups. Just grab your sunscreen and go — we've got everything else covered!

4.95 out of 5 average rating, 111 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, 128 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

Townhouse in Madeira Beach

A view through a screened balcony showcases a sandy beach with individuals enjoying the sun. Colorful beach umbrellas and towels are positioned on the sand, and the calm ocean stretches into the distance under a clear blue sky.

Villa Madeira

Property Type Condo Unit Code VM204 Beds 1 king bed, 1 queen bed, 2 twin beds Bathrooms 2 bathrooms Rooms Sleeps 6 Reserved Parking for 1 Vehicle, Guest Parking for Others Pets No pets allowed. Living Central Air Conditioning, High Speed Internet, Ironing Board, Linens, Washer & Dryer Business Nearby ATM, Nearby Bank, Nearby Internet Cafe Kitchen Coffee Maker, Cookware, Full Kitchen, Entertainment Smart TV Outdoor Balcony, Beach, Outdoor Shower, Pool Geographic Close to John's Pass, On Beach

4.89 out of 5 average rating, 156 reviews

4.87 out of 5 average rating, 175 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!

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, 129 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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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.

4.89 out of 5 average rating, 214 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, 184 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.

4.96 out of 5 average rating, 167 reviews

COASTAL CHIC! Luxury Apartment with Oceanviews

Welcome to our Gulf View Condo SEASIDE #1604 at the "Madeira Bay Resort" - just steps from the beautiful white-sanded Beach and famous John's Pass! Built in 2020, you will enjoy brand new amenities, luxurious furnishings, memory foam beds, an electric fireplace, a gourmet kitchen and all beach essentials, so you only have to pack your flip flops and come on over!

Popular amenities for Madeira Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

5.0 out of 5 average rating, 227 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A spacious backyard is highlighted by a solar heated pool, surrounded by lush greenery and native plants. Comfortable lounge chairs face the water, with colorful floatation devices resting nearby. A shaded area is provided by a patterned umbrella, offering a spot to relax and enjoy the scenery.

4.99 out of 5 average rating, 140 reviews

Mad Beach HideAway • Private Pool • 4 Bed • 3 Bath

4.97 out of 5 average rating, 242 reviews

Coastal Pool Retreat *5 Min to Madeira Beach Sand

4.98 out of 5 average rating, 189 reviews

Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

4.94 out of 5 average rating, 339 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

4.89 out of 5 average rating, 145 reviews

A spacious living area features a large, curved sectional sofa adorned with decorative cushions. A circular coffee table rests on a soft area rug, while a television is mounted on a light-colored wall. Natural light enters through multiple windows, enhancing the bright space.

Home in Largo

Heated Saltwater Pool Home 3 Miles to Beach

4.9 out of 5 average rating, 128 reviews

A heated pool area is surrounded by tropical plants and palm trees. A tiki hut provides shaded seating, and lounging chairs are positioned around the pool. A textured stone deck complements the inviting water of the pool, creating a relaxed atmosphere for guests.

Home in Largo

Tiki House •Sleeps 12 •Walk to Beach + Heated Pool

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.

4.9 out of 5 average rating, 187 reviews

Hibernate in our Bear Creek Home

Condo rentals with a pool

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.

4.91 out of 5 average rating, 117 reviews

Luxury Seashell Oceanfront Condo with Pool

4.98 out of 5 average rating, 123 reviews

Ocean View Perfect Oasis to Relax!

4.85 out of 5 average rating, 104 reviews

Great Location at Quiet and Private Building

4.97 out of 5 average rating, 235 reviews

*Shore Thing* Walk to Beach | Intercoastal Views

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, 109 reviews

Special 10/24-11/21,26-All Room Direct Beach Front

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.

A private balcony showcases a stunning sunset view, framed by palm trees. The spacious area features a green chair and overlooks the resort's pool and surrounding buildings, creating a serene outdoor space for relaxation.

4.98 out of 5 average rating, 164 reviews

Sunset Nest: Two Bedroom Condo with Sunset Views

5.0 out of 5 average rating, 102 reviews

Condo in Sunset Beach

Glorious Sunsets - Beachfront 2BR Condo

Other vacation rentals with a pool

Bungalow in Indian Shores

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.97 out of 5 average rating, 200 reviews

A spacious living area features large windows allowing natural light and offering ocean views. Comfortable sofas are arranged around a central coffee table, while a flat-screen TV is mounted on the wall. A beach-themed artwork adds a colorful touch to the room.

5.0 out of 5 average rating, 30 reviews

Beachfront Retreat w/ Panoramic Views and Pool

5.0 out of 5 average rating, 7 reviews

Renovated 2-Bedroom Condo by Waterway

A spacious living area is furnished with a wraparound grey couch and two blue accent chairs. A round coffee table is centered in front, with a decorative bowl placed atop. Large windows allow natural light to fill the room and offer a view of the outdoor surroundings.

5.0 out of 5 average rating, 47 reviews

New Luxury 3BR Walk to Beach Pool, Spa + Parking

4.95 out of 5 average rating, 38 reviews

Direct Beachfront Corner 3BR|GulfView Pool|Madeira

4.95 out of 5 average rating, 19 reviews

Bay-View 2BR / Heated Pool, Steps to Madeira Beach

5.0 out of 5 average rating, 62 reviews

An open-concept living space features a modern kitchen with stainless steel appliances and white cabinetry. A large island with seating for four is present. Natural light floods the area through expansive windows, showcasing water views and creating a bright atmosphere.

Condo in Redington Beach

Luxury Penthouse Beach Condo

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