Holiday rentals with a pool in Johns Pass

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Top-rated rentals with a pool in Johns Pass

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
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.
Apartment in Treasure Island
4.9 out of 5 average rating, 121 reviews

2/2 Newly remodeled Beach Front - Sunset Vistas

Amenities/Location-Newly Remodeled Oceanview Condo with Balcony, Gorgeous Beach, Sleeps 6, king/master, queen/guest, queen sleeper, in unit washer/dryer, Smart 60- & 55-inch tv’s, cable, Wi-Fi, equipped kitchen, heated pool, kids pool, two jacuzzies, Tiki Bar, Cafe, rental bikes, Ping-Pong, Volleyball, Gym, Business Center, free covered parking, 5 day to monthly rentals. - Laundry detergent shampoo, conditioner and body wash, Beach Towels provided - 1/2 A MILE TO JOHNS PASS & No Resort Fees

Top guest favourite
Apartment in Treasure Island
4.95 out of 5 average rating, 145 reviews

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

Top guest favourite
Apartment in Treasure Island
4.96 out of 5 average rating, 187 reviews

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Retreat 🏖️ 🌅 Sunset Serenity - Unwind with views as the sun melts into the horizon. 🚶 Beachside Bliss -Just steps away from powdery sands & shimmering waters of Treasure Island. 🐬 Marine Magic Awaits - Watch dolphins dance and manatees glide right by! ✨ Stylish Coastal Vibes - Immerse yourself modern interiors with a breezy beach flair. 🍽️ Chef’s Dream - Whip up delicious meals in a fully stocked, luxury kitchen. 👩‍💼 Service with Heart - Your comfort is my priority!

Top guest favourite
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.
Apartment in Treasure Island
4.99 out of 5 average rating, 204 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.

Top guest favourite
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.
Houseboat in Madeira Beach
4.97 out of 5 average rating, 106 reviews

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**

Guest favourite
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
4.85 out of 5 average rating, 144 reviews

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!

Top guest favourite
A resort-style swimming pool is surrounded by a spacious patio featuring multiple lounge chairs. The building's exterior is light-colored, with large windows and an inviting entryway. Tropical plants are positioned around the pool area, contributing to a relaxing environment.
Apartment in Treasure Island
4.94 out of 5 average rating, 219 reviews

Where the Sun Meets the Water

This first-story 670 sq-ft, 1BR/1BA condo, is located just a couple of blocks from the white sands of the Treasure Island beaches. Stroll to John’s Pass to find ample local dining and shopping options. Guests have full access to the grounds including a resort-style pool, a shared fishing dock, and a waterfront patio equipped with gas grills, perfect for enjoying a meal and watching as dolphins and birds pass by. 2025. Come visit & stay a while! Operated by Summer Bloom Estates LLC

Guest favourite
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.
Apartment in Treasure Island
4.89 out of 5 average rating, 157 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.

Top guest favourite
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.
Apartment in Madeira Beach
4.98 out of 5 average rating, 156 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.

Top guest favourite
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.
Apartment in Madeira Beach
4.99 out of 5 average rating, 212 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.

Top guest favourite
A light-filled living area showcases large windows that offer views of the outside. A comfortable sofa is positioned next to a wooden coffee table. A dining table with four chairs sits nearby, accompanied by a lamp on a side table, enhancing the space's functionality.
Flat in Madeira Beach
4.9 out of 5 average rating, 152 reviews

2 Bedroom 1 Bath Upstairs MODERN Apt NO PETS

Pools are open and wifi works great! Completely Renovated and Beautiful!2 Bedroom 1 Bathroom Upstairs unit w/t Full Kitchen. This unit sleeps 6 people. Sorry No Pets Allowed. Each bedroom has a queen size bed and the sofa turns into a queen bed as well. Watch a Movie on the 70" TV in the Living Room or Play a Game on the PlayStation 4! Or Retreat to one of the 2 bedrooms each with a 55" TV. Full Kitchen includes Stove

Guest favourite
A bright living area is furnished with a light-colored sofa and two chairs, providing a comfortable space for relaxation. A dining table for four is visible in the background, along with a fully equipped kitchen. Natural light streams in through large sliding doors, revealing views of the Gulf.
Apartment in Madeira Beach
4.84 out of 5 average rating, 204 reviews

Gulf of Mexico Beach Retreat | Madeira/John's Pass

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Enjoy Gulf views and modern coastal luxury in this Madeira Beach condo—just steps from the sand and John’s Pass Village. Stylishly furnished with open living, full kitchen, and private balcony for ocean breezes. Resort-style amenities, dining, and entertainment are all nearby for the ultimate beach escape!

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