Holiday rentals in Sand Key

Pet Friendly Pool Oasis St Pete/Gulfport

Exceptionally private artist's home with a salt pool ( not heated) in a tropical landscaped fenced backyard and a large screened porch, surrounded by palm trees. 10 mns to St Pete beach , Treasure Island, Sunset beach or downtown St Petersburg. 5 mns to the old Florida downtown Gulfport and one block to pinellas trail. Our Eco and pet friendly ,(only green cleaning products and no pesticides) 1400 sqft home ( plus the 300 sqft porch) home is in a safe residential area, close to everything.

Waterfront Penthouse Rooftop Casita 5-min to Beach

Premier Waterfront Penthouse on Clearwater Beach This 3 Bedrooms ( king each)+ bonus room ( pull out couch) 4 bath 4 levels 2954 sq ft Elevator is accessible, and fully furnished with a boat slip and lift. Relax and watch the sunset from your gorgeous rooftop oasis like no other, a one-of-a-kind 20 x 20 beautifully finished living area with spectacular views and a Viking outdoor grill,tops off this rare rooftop dream. 5 min walk and you will be at Sand Beaches, restaurants, and shopping.

CBC 1-16C– Gulf front with pool, hot tub & gym!

⭐Important Notice Regarding Balcony Access⭐ ~ The balcony for this unit is currently closed, but you will still be able to enjoy beautiful beach views from inside the condo. ~ Please also note that the pool in Building #1 is temporarily closed; however, guests are welcome to use the pool in Building #2 throughout their stay. ~ Guests may experience occasional noise during business hours due to the construction on the balconies. ~ Take advantage of the already deeply discounted rates!

True beachfront property! 3 ocean view decks!

Welcome to "Beach Blues" where you'll only have the "Blues" when you are leaving! Newly renovated decks and beach level travertine patio allows you full ocean view from 3 levels and direct beach access in one step! Professionally and comfortably decorated inside too! No more lugging your beach items as we provide chairs, umbrella, sand toys, and beach towels. Perfectly located close to restaurants, groceries and activities. Few miles from Clearwater, Dunedin and the new St Pete Pier.

New Beach Retreat– Hammock, PAC-MAN, Steps 2 Sand.

Sandy Feet Cottage is a newly remodeled beach retreat just 2 minutes from Indian Rocks Beach. Enjoy an open layout, new furnishings, a spa-style bath, and a private yard with fire pit, hammock, and patio. Walk to dining, bars, and shops—your stylish Gulf Coast escape. ***NEW AIRBNB PRICING UPDATE*** Starting mid-October 2025, Airbnb will display all-in pricing—including a 15.5% Airbnb service fee (charged directly by Airbnb to the host), plus cleaning and pet fees if applicable!

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U3 ♥

✳ DAYDREAMERS ✳ This new Indian Rocks Beach condo offers convenient access to white sand beaches of the Gulf. Watch as dolphins swim into the sunset and beachcombers look for shells and buried treasure. With a coastal beachy atmosphere, this beauty will take you out of your element. This home features ultra comfy bedding for maximum rest & relaxation. So dream a little dream, while relaxing your day away. The unique coastal design compliments all of the things IRB has to offer.

10 Minutes to Beaches! Thyme (to Coast) House

Ready to create lasting memories? Book your Florida dream vacation today! Unwind and recharge at this perfect Florida getaway! Our charming rental is just minutes from the stunning beaches Pinellas County offers. Soak up the sun and crystal-clear waters, all within a 10-minute drive. Need to stay connected? We've got you covered with blazing-fast 1G Wi-Fi and a dedicated workstation, making it easy to balance work and play during your stay.

Beach house, pool table, golf cart, private dock!

Beach and water surround you. Beautiful inside and out! Enjoy the modern and bright open kitchen, dining and living areas with plenty of room for the family to relax, have fun and share memories. Every detail has been carefully thought out, and updated. Everything's brand new! This is an upscale, coastal, two-story waterfront home. You rent the entire property, three bedrooms, three baths and do not share the property with anyone.

Madeira Beach and John's Pass #1

Beautiful new rental for your beach enjoyment. Brand new kitchens with granite counter tops and new appliances. Washer and dryers in each unit. Brand new Bathrooms with tiled showers. New tank less water heater. Private back patio with a gas grill for cooking all that fresh seafood from the Gulf of Mexico. Quiet street and walking distance to restaurants, entertainment and bike/kayak rentals and 1 block from beach.

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Overlooking Downtown Dunedin Two Bedroom apartment

Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. First floor 2 bedroom apartment is totally renovated. Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more, or just relax and watch the action from the front porch.

Beachfront House, Steps to Sand and Sunset

Relax with the whole family at this peaceful 3-story beach retreat! Just steps from the soft white sands of Indian Rocks Beach. Enjoy balconies on the 2nd and 3rd floors with ocean breezes, a quiet neighborhood, and an unbeatable location near dining and fun. Clean, spacious, and pet-friendly — the perfect coastal getaway!