Holiday rentals with a pool in Gulfport

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and pool. Visit nearby great restaurants, John's Pass Boardwalk and live music.

The Salty Dunes… Adorable Studio near downtown

Welcome to the Salty Dunes! Located in Historic Roser Park, a cobble street, tree-lined storybook-like neighborhood. From here it’s just a short 2 mile bike ride to downtown St. Pete, the new Pier, Beach Drive and some of the best restaurants, museums and parks St Pete has to offer. We’re a quick 15-20 min drive to some of Florida’s best beaches and only a 25 min drive to Tampa International Airport or the St. Petersburg/Clearwater Airport. This place is perfect for couples or solo adventurers.

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.

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

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!

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Snowbird paradise! Waterfront, pool, hottub

Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

Updated Condo minutes from the beach - heated pool

Welcome to this fabulous and spacious newly updated condo close to the beach and many restaurants. Closest beach is 12 min walk or 2 min drive. John Pass Village is only 6 minutes drive, Downtown St Pete and newly re-opened St Pete Pier is a must visit for either night life or nice dinner. Egan Park and tennis courts are across the street. Pool is in the building- hours of operatio dusk to down.Pool is heated to 82f during the day.Roku TV's in the unit.

Villa Splash, 1 room pool suite

Tropical pool villa in central St Pete built in 2022, only 1 mile from Pinellas Trail, 2 miles from downtown restaurants and 5 miles from Treasure Island Beach. One room efficiency includes a comfortable queen size murphy bed, full bathroom (w/shower-no tub), large flat screen tv, with wet bar, microwave & coffee maker. Guests will have private access to pool. Smoking is NOT permitted on property and will be reported.

Bungalow Heated Pool Home 10 minutes to Beaches

Welcome to the Starfruit House. A completely renovated three bedroom two bathroom beach cottage with a 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.

Suite Retreat in Southwest St. Petersburg

Cozy suite just 10 minutes to beaches or to vibrant downtown St. Petersburg. Parking on the premises. Relax in your private quarters supplied with plenty of creature comforts that make you feel like you are in your home away from home. Comfortably laid out living and dining area; kitchenette, bathroom, and bedroom with French doors leading you out to the pool.

Heron's Hideaway- Studio by the bay!

Newly remodeled studio with luxury in mind! Keep it simple at this peaceful and centrally-located condo on the bay! Heron's Hideaway is located on the 3rd floor with unobstructed views of the intercoastal waterway! Views of the marina, boats, dolphins and incredible sunsets! This cozy studio is packed with everything you need to enjoy paradise!