ITrip - St. Petersburg Beaches

ITrip - St. Petersburg Beaches Vacation Rental Management Services
Homeowners who list with iTrip receive a full-service short-term rental management program. Your destination in St.

Rental Guest Benefits: Secure online booking, property inspection before every checkin, professional and courteous 24hr team Choose from 200 properties for your beach or bay side vacation. We can offer the perfect getaway at one of our studio, 1, 2, or 3 bedroom condos, cottages, or private houses. We provide an easy online booking process and friendly customer service. During your vacation venture out for water activities like boating, sailing, para-sailing, jet skiing, paddle boarding, swimming, fishing, dolphin watching, kayaking, and shelling. Fort De Soto State Park is a great for a picnic, bird watching and exploring. Try nearby golfing, museums, and shopping. There are plenty of restaurants, bars, ice cream, and shopping within walking distance of all of our vacation rentals. Located less than two hours from Disney and the Orlando attractions, and only four hours from Miami and the Keys. Petersburg Beaches is the center of it all.

πŸŽƒ Fall is officially here! Mark your calendars for these upcoming events:🌊 Taste of the Beaches | Oct 3-11🦞 Johns Pass S...
09/22/2026

πŸŽƒ Fall is officially here!

Mark your calendars for these upcoming events:

🌊 Taste of the Beaches | Oct 3-11
🦞 Johns Pass Seafood Fest | Oct 23-25
πŸ–οΈ Sanding Ovations | Nov 19-22 & 28-29
πŸ‘» Howl-O-Scream at Busch Gardens | Select nights, Sep-Oct

Ask us about free tickets to select activities! Call (727) 472-9494 or email [email protected] 🧑

πŸŽ‰ Celebrating 1️⃣6️⃣ Years and the Besties Award! πŸ†Our front line team + spouses had a great time at Empower Adventures ...
09/17/2026

πŸŽ‰ Celebrating 1️⃣6️⃣ Years and the Besties Award! πŸ†
Our front line team + spouses had a great time at Empower Adventures Tampa Bay team building & zip lining - taking iTrip to new heights, literally! This outing was tops!

We πŸ’™ the 727 t-shirt design by Clancy Riehm - Thank you to Oliver and team Visit St. Pete-Clearwater!

Here’s to 16 years of vacation rental adventure! 🌊

09/16/2026

πŸ–οΈ Welcome to the Collection
Say hello to our latest addition β€” 16 Birdsong, an updated one-bedroom condo steps from the beach at a beachfront resort in Treasure Island. Sugar-white sand right outside your door, a sparkling heated pool, a shaded BBQ area, and a shuffleboard court for some old-school Florida fun.

Inside, a full kitchen, comfortable living space, and a king bed ready for a good night's sleep after a day in the sun. Publix just down the road for easy stocking up.

Sand, sea oats, and swaying palms right outside β€” this one has all the little details that make a Florida beach trip feel like Florida.

Now accepting bookings β€” link in comments to grab your dates!

09/13/2026

A Tampa Bay local, Ariana is bringing you fun things to do in the area! First up: near Skyline Resort. Drop your bags and head to Candy Kitchen Madeira Beach for some homemade ice cream. Thanks Phil for your friendly service. 🍦

Have you been? Let us know your favorite flavor in the comments! πŸ‘‡
Be sure to get your free scoop on your next stay with iTrip!

πŸ–οΈ A day at 7 Beach Club at Pass-A-Grille looks like this... πŸ–οΈ- Morning coffee on the balcony, watching the world wake ...
09/09/2026

πŸ–οΈ A day at 7 Beach Club at Pass-A-Grille looks like this... πŸ–οΈ

- Morning coffee on the balcony, watching the world wake up
- Unwind in the living room after a day in the sun
- Crawl into that king bed for a great night's sleep
- An afternoon dip in the pool when the beach gets too warm
- Then strolling to dinner β€” restaurants and beach access just steps away

This is the Pass-A-Grille life. Swipe through and see for yourself πŸ‘‰

Book your stay β€” link in comments!

09/02/2026

🌊 Take a tour of 401 Chambre with Ariana! πŸ–οΈ
This 4th-floor corner unit β€” steps from the sand with a view that never gets old. A king suite, two twins, and a queen sleeper sofa mean room for the whole crew, plus a full kitchen and in-unit laundry make it feel like home. Beach out front, pool & hot tub downstairs, zero traffic noise β€” this is Madeira Beach living πŸšβ˜€οΈ

08/31/2026

πŸ† We won the Besties' pick for Best Vacation Rentals 2026, presented by Visit St. Pete-Clearwater! πŸŽ‰Thank you to everyone who voted for us πŸ™

This win belongs to our whole network: outstanding local staff, iTrip, our partners, cleaners, franchisees, contractors, our owners who trust us with their properties, and most of all β€” the guests who choose us to make their vacation memories unforgettable πŸ’™πŸ–οΈ

What an honor to be named Best Vacation Rentals alongside the best restaurants, bars, museums, hotels, and attractions in the area β€” with the Florida Orchestra setting the mood all evening.

πŸ”— We’re proud to be included here: https://www.visitstpeteclearwater.com/best-places-to-stay

08/30/2026

Grab your flip flops and head to the beach - it's National Beach Day! 🩴🌊 See you there!

Address

13999 Gulf Boulevard
Madeira Beach, FL
33708

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