Holiday rentals with outdoor seating in Gulfport

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2 with an air mattress upon request, TV with streaming options, fun decorations, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. Pets are welcome.

Shipwreck Bungalow

Shipwreck Bungalow, your own private paradise! Nestled in a quaint Gulfport neighborhood. Just 10 minutes from St. Pete beach, 10 minutes from lively downtown St. Pete and a few short minutes from funky downtown Gulfport. The Bungalow is surrounded by palms, tropical plants and flowers, beautiful outdoor shower, Tiki bar, heated stock tank pool, fire pit, outdoor games, grill and spacious outdoor seating area. Enjoy lounging by the pool or exploring all this sunny area has to offer!

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile from Gulfport's beach blvd. Where you can shop, dine, or stroll the beach. 6 miles away will take you to the famous St Pete Beach or the St Pete pier.

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

Cozy St Pete Suite near beaches

Enjoy a nice comfortable in law suite, fully furnished with full kitchen and grand master bathroom. Toiletries included for your convenience. Quick commute to Tyrone Mall for shopping and dining. Beautiful sandy beaches of Madeira, Redington and St Pete Beach are minutes away. Enjoy a night out on St Pete Downtown also within short distances. Feel right at home with a clean fresh and cool Florida Suite.

Bungalow Heated Pool Home 10 minutes to Beaches

Welcome to the Starfruit House. A completely renovated three bedroom two bathroom beach cottage with a brand new in-ground heated pool! This home features the feel of old Key West with all new modern updates. Within a few miles of the most popular beaches in the area, minutes to downtown St. Pete, and a quick bike ride to Gulfport. Enjoy the tropical feel of the outdoors, and then come inside to relax.

The Boho - 2BR Gulfport Waterfront District House

Boho inspired cottage in the heart of the Gulfport Waterfront District. Steps away from Gulfport beach, restaurants, and nightlife. Enjoy strolling along Beach Boulevard where you'll find local coffee shops, ice cream parlors, Gulfport brewery, and eclectic shops. Relax in the comfort of your backyard oasis or enjoy some fun in the sun with the best Gulfport has to offer right outside your back door.