Our mission is to serve the 50+ traveler. We want to inspire you to explore new destinations, discover new experiences, and savor the journey.
You’ve earned this. You’ve earned the time off. You’ve earned the chance to get away. And now it’s time for you and yours to take on full snowbird status and head to Florida for a month or more. Where do you start, you might ask? We’re here to help! If the Pinellas Peninsula in Florida sounds appealing to you (I’ve been, trust me… it’s appealing), then we hope you take a few moments to look at these 20 rental options selected just for you. These are nearly exclusively designed for couples — your chance to truly get away from it all!
While there are plenty more options than what we are offering up here, we think these rentals in Madeira Beach (Redington area), Sand Key/Clearwater Beach, Indian Shores, Treasure Island/Sunset Beach, and St. Petersburg/St. Pete Beach will be a great start to find what you’re looking for. If by chance you’re looking for more to do than relax on the beach or hang out in one of these amazing rentals, you’ll find lots to do in the St. Petersburg area and in Clearwater or Clearwater Beach. What are you waiting for?
This gorgeous penthouse suite , located within the Sandpearl Resort and Spa on Clearwater Beach, is situated on the top floor and was completely redone in May of 2020. The private balcony off of the living room affords you amazing views of the city and harbor. You’ll love the California king bed in the master suite that connects to the bathroom, large shower, and Jacuzzi tub. This suite faces to the east to give you a spectacular view of Mandalay Bay. This gorgeous gem is a must-see!
This touch of paradise at Crescent Beach Club offers a 180-degree view of the Gulf of Mexico from the balcony and incredible views from every room. Located on the sixth floor, this luxury condo sits right on the beach, and the balcony — which includes a table, chairs, and loungers — is accessible from both the living room and master bedroom. Ready to head to the beach? This unit includes beach chairs, beach towels, and an umbrella. The Crescent Beach Club features two heated gulf-side pools, beach access, two outside spas, a tennis court, indoor hot tub, and much more. This condo and complex offer you the ultimate in luxury — don’t pass up on this one!
Enjoy a breathtaking view of the Gulf of Mexico from the 18th floor of the Crescent Beach Club 2 complex just steps from the beach. Newly remodeled and comfortably furnished, the floor-to-ceiling glass doors take you from your living room couch or king-sized bed to your balcony. From there, you are going to love the 180-degree westward view over a morning cup of coffee or an evening-time cocktail. Crescent Beach Club 2 is conveniently located and offers a pool, Jacuzzi spa, tennis courts, and more. You’re sure to love Pier 60 and all of the beautiful sights of Clearwater Beach!
This gorgeous 12th floor hideaway at the Crescent Beach Club sits right on the beach and offers a 180-degree view of the Gulf of Mexico. Located on Sand Key, relax while watching the sailboats and dolphins from your kitchen or take in beautiful Florida sunsets from your patio — which comes equipped with a bistro table and chairs. Among the amenities at Crescent Beach Club are a swimming pool, fitness center, sauna, two hot tubs, and more. You’re going to love the views!
Are you ready to book a trip to paradise? If so, this relaxing condo at Ocean Sands is for you! This 1,000-square-foot condo sits on the fourth floor, offering panoramic views and sunsets from the private balcony overlooking the Gulf of Mexico. The complex provides guests with a heated private pool and spa, accessible by keypad gates for residents and guests only. You’re going to love the living room and master bedroom, each of which feature a wall of glass that slides open to your balcony. Beach chairs, beach towels, and a beach umbrella are in the unit and yours to use, so you can pack just a little more lightly.
If amazing Gulf views in an upscale and secluded condo sounds good to you, then this rental is a must-see! Close to John’s Pass, restaurants, and shops, and within walking distance to Candy Kitchen, this centrally-located beauty is decorated “beach chic” with beach appointments throughout the living and family rooms. Step outside and enjoy your private, oversized balcony and watch the dolphins frolic!
This updated, ground-floor condo at Sunglow Seaside includes free lounger chairs, Wi-Fi, a barbecue, and a private umbrella patio table. This one is a great value! You’re going to love the majestic sunset views, your private covered porch, and your location — right in the middle of the three barrier reef islands. It’s located due north of Redington, Indian Shores, and Clearwater Beach, and is south of Treasure Island, Sunset Beach, and St. Pete Beach.
This “Old Florida” tropical beach cottage is full of modern amenities, privacy, and charm. You’ll have everything you need here including a fully-equipped kitchen, beach towels, and chairs. This location offers you no streets to cross to get to the beach, and is within walking distance to John’s Pass, restaurants, shopping, dolphin watching, and more. This little cottage is bright and fun and waiting for you!
There are a lot of options to choose from when looking at beach rentals, but when you come across the chance to stay in a beach house, you can’t pass it up! This cozy one-bedroom house is one of the last beach houses on Indian Shores, and features granite countertops, a microwave, stove, toaster, coffee maker, refrigerator, Wi-Fi, and is near lots of local amenities. Jet ski rentals and fishing charters are close by at John’s Pass. Or head the other direction 10 minutes and check out Clearwater Beach. You don’t want to miss out on this one!
From your porch to the sand, the beachfront cottage with old Florida charm is just steps from the Gulf of Mexico and offers fantastic sunset views! With a private carport, you can park your car and enter this house without climbing any stairs. Inside, you’ll find an open-floor plan, well-stocked kitchen, new bathroom, and new furnishings. Add the fun beach decor inside and this cottage is definitely worth checking out.
Just steps from Indian Shores Beach, this third-floor condo comes in a little less expensive with the caveat that it does not have a balcony or an ocean view. It does, though, sit just steps from the beach and is conveniently located at Villas 3 Resort. Here, you’ll find easy access to plenty of leisure and recreational activities. Be sure to take advantage of the heated pool and patio that overlook the Gulf of Mexico!
With nothing obstructing your private, breathtaking ocean view, this first floor beachfront condo is a little slice of heaven on Indian Shores , offering quick and easy access to the sand and shore. Located directly across from the highly-rated Salt Rock Grille, Indian Shores sits conveniently close to Clearwater, St. Petersburg, and Tampa. The breathtaking ocean view offers the ultimate in relaxation!
If you’re looking for a beachfront “Parrotdise” condo with beautiful beachfront views of the gulf , then this vacationer’s delight might just be for you! Equipped with a large, private deck, you’re going to love watching the sea birds, parrots, and dolphins. Or take long walks on the beautiful, sandy beach. Looking to relax after your walk? Have a seat on the garden patio that overlooks the beach and take in a gorgeous Florida sunset. There are lots of amenities nearby — enjoy “Parrotdise” on your next vacation!
Located in the heart of Treasure Island, this Island Breeze motif condo is the perfect spot to take in stunning views of the Gulf of Mexico from your private balcony. Step out of your cozy unit at the Bilmar Beach Resort to take a dip in one of the heated pools, located directly beneath your unit. Or sit on your balcony to sip morning coffee and listen to the relaxing ocean sounds. This gem offers beautiful views with lots to do nearby!
With gorgeous beach and gulf views, this beachfront condo with a private deck offers the sights and sounds of gentle waves, sea birds, parrots, dolphins, and more — all at a convenient and centrally-located spot. You’re going to love the cozy interior of this 600-square-foot unit. But, you’ll no doubt love even more relaxing under the shade tree while taking in gorgeous sunsets on the garden patio that overlooks the beach. Check out the provided photos for those amazing deck views!
Just steps from the beach, the Harbor House Sunset Beach Getaway is a newly-renovated condo with amazing views of the Gulf of Mexico out front and the Intracoastal Waterway in the back. With a heated pool at your disposal, take advantage of your easy beach access — the beach towels, beach chairs, and umbrella are provided. Harbor House is walking distance to local restaurants, shops, and bars. This one is cozy and clean at a reasonable price!
This studio located in the heart of Historic Pass-A-Grille sits right on the Gulf of Mexico — a perfect spot for your cozy getaway! Completely remodeled and fully furnished, Pass-A-Grille is close enough to the action to be convenient yet remains a quaint beach community. This one is definitely worth a look — you’ll be glad you did.
This Tropical Courtyard Paradise offers a private entrance and courtyard along with a spacious heated pool. Just a 1-minute walk to Upham Beach or the fun on Gulf Boulevard, this unit comes at an affordable price in a premium beach location. Ready to hit the pool or the beach? A cooler, beach chairs, pool noodles, flip flops, a boogie board, beach towels, a carry-on wagon, and more are available for you. Be sure to take the time to relax on the private, shaded courtyard!
Don’t come looking for us, we’ve Gone Gulfin’ ! This corner unit is nicely decorated and provides easy access to historic Pass-A-Grille. You’ll spend your mornings enjoying coffee and evenings sipping a cocktail on your porch, and in-between, spend some time in the heated pool. Pass-A-Grille is located within walking distance of shops, restaurants, and bars on 8th Avenue, or stroll a block to the Merry Pier for bird watching, bike rentals, fishing, or a sunset cruise.
This Sweet Spot in Downtown St. Pete is within walking distance of just about everything! This spectacular condo is near some amazing museums, including The Dali, Museum of Fine Arts, Holocaust Museum, and St. Pete History Museum, to name a few. Is the restaurant scene more your thing? There is a long list of restaurants and breweries around. Or pay a visit to the local shops, art galleries, music venues, or boutiques. If you’re a sports fan, head over to Al Lang Stadium to watch the Tampa Bay Rowdies play soccer, or Tropicana Field to take in a Tampa Bay Rays baseball game. There’s so much to do — this one is a must-see!
To check out even more snowbird rentals around Florida: