Holiday rentals with a kayak in Gulfport

Modern Townhouse right across beach! Table tennis

3 Bedroom/2.5 Bath modern townhome across street from beach, 2 large balconies off of living room and master bedroom. Lush landscaping. Enjoy meals in the beautiful dining area. Full equipped kitchen! Parking garage 1 car and driveway parking available. Sleeps 10. We rent all year round due to beautiful Florida weather. Walking distance to beach, restaurants, parks, basketball court, volleyball. Close to Johns Pass, 1 mile - Indian Rocks Beach. Tampa, Clearwater and St. Pete are a short drive.

Sunset Cove Bungalow

Kick back & relax in this calm, stylish waterfront bungalow. Located on Boca Ciega Bay in the quirky town of Gulfport, this special little house is the perfect getaway. Bikes, kayaks, paddleboard, beach chairs, umbrellas are all in the boathouse, ready for your daily adventures! Fully loaded kitchen & large dining room make meals at home easy, but Gulfport also has a wide array of dining options including seafood, Italian, French, Greek & more. (Adults only please as we are waterfront w/ a pool)

Central Bungalow Near DTSP with Swim Spa!

Vacation like a local at this centrally located bungalow style residence. This 3BR 2 Bath home is set to entertain our guests. Indoor living space Includes two sitting areas, fireplace and workstation. The dining room and kitchen welcomes you home with all the amenities you need to keep everyone happy. For our outdoor lovers, we welcome you to the tavern. This fully functional outdoor living space includes a grill, tv, sectional seating, full size bar. Be our guest and enjoy St Pete like a local

Charming 2BR Condo Near Ft. De Soto

Come enjoy your next vacation, holiday, or winter escape in Tierra Verde, Florida! Watch the sun rise over Boca Ciega bay from the balcony of this beautiful, updated first floor condo. This 2 bedroom/2 full bath unit has been thoughtfully designed and furnished with everything you need to enjoy an stress-free get-a-way that feels like home. This rental has an official Certificate of Use through Pinellas County as a Short Term Rental as well as a rental license through the state of Florida.

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.

Waterfront pool home w/dock, firepit, kayaks

Waterfront pool home minutes from downtown St. Pete. Gorgeous water views from all living areas, brand new pool, screened-in porch and large deck area for waterfront relaxing. Dolphins, manatees and gorgeous sunsets await you at this modern and perfectly located vacation oasis. This home offers easy access to award-winning restaurants, lively bars, a thriving arts scene, and many amazing beaches. Public boat launch, basketball and pickleball courts just minutes away.

The Olivia

Modern organic entire home with elevated amenities, a resort-style pool and private outdoor oasis. This luxurious home is perfect for resting, retreating and entertaining. Walking distance to the best local produce market, restaurants and shops for everything you need and only a 9 minute drive to the most famous Upham & St. Pete Beach. This tropical paradise is truly one of a kind with "low-tox" living amenities we've consciously curated with your well-being mind!

SolMate 2/2, kayaks, beach, views, boat slip

Newly renovated beach home, bright and beautifully appointed 2 bed/2 bath second floor condo with balcony overlooking Boca Ciega Bay. Modern beach decor. Only few steps to Treasure Island’s white sandy BEACH. Incredible water views from every window. 3 KAYAKS available (must sign waiver). Fun activities including ping pong, corn hole, etc. in common area. Only 6 units on property. Featured on HGTV Beachfront Bargain Hunt (Season 27 Episode 10).

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Steps 2 Beach- Cottage w/king bd +2bikes +parking

The Seashell cottage A Charming Old Florida beach cottage just steps from the sand in quiet, walkable Pass-a-Grille. Bright, clean, and thoughtfully updated with a comfy king bed, full kitchen, great shower pressure, and private front & back patios. Bikes and beach gear included, so a car isn’t needed. A cozy, homey alternative to crowded condos—perfect for couples, sunset walks, small families, 1 pet families, and relaxing beach days.

Waterfront Condo with Boat Slip & Fishing Dock

Escape to this peaceful, 2-bedroom waterfront condo on Boca Ciega Bay. Perfect for families, this ground-floor retreat offers stunning bay views, a heated pool, and a private dock. Rent your own private boat slip or just fish right off the dock. Enjoy a bright, modern space that comfortably sleeps your group. You're just a short walk from the beach, local dining, and vibrant nightlife. Your serene coastal getaway awaits!