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Casa Plumeria- Luxe guesthouse with king bed

Perfect St. Petersburg getaway! This spacious and completely remodeled unit is located in a quiet residential area but is close to everything the area has to offer. Downtown St. Pete with it's new pier, spa beach, waterfront parks, many restaurants and breweries is less than 5 miles away. Sawgrass Park and Weedon Island Nature Preserve (~2 miles) offers great nature trails, kayaking, fishing and birding options. Some of the best beaches in the world are less than 30 minutes away. TIA is 20 mins.

Pearl of the Sea, 1 BDRM, 2 min walk to the beach

Please note, the gym, jacuzzi, and hot tub are temporarily closed(hurricane damage) Completely remodeled, beach theme decorated, a beautifully furnished second-floor condo just steps away from the white silky sandy beach! Ideal for romantic vacations, honeymoon escapes, and getaways! Located in Madeira Beach Yacht Club, a private gated community, free parking, high-speed WI-FI, TV cable, Netflix, 2 outdoor heated swimming pools, and fishing piers. Please, book at least 7 days before your arrival

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

Villa at Harbor House "Villas by Christine"

Welcome to The Villa at Harbor House, located just steps from Safety Harbor’s Main Street, ranked the #10 Main Street by USA Today in 2025. Enjoy convenient walkable access to charming shops, dining, and pubs. This villa is perfect for solo travelers or couples, offering a queen bedroom, fully stocked kitchen, spacious living room, smart TVs, full laundry, and more. Pet-friendly ($100 fee). Beach gear included. For larger groups, consider booking Villa Key West or Villa Italia, steps away.

Tootsie’s Beachside Retreat-New Heated Pool

LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

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.

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

SHEEK and Glam- heated pool Updated! 3 mi to beach

UPDATED modern Light and bright colorful condo w FREE HEATED POOL! First floor NO stairs. 2 miles from the beach. Crazy FAST WIFI- at 600mbps !!! Great central location close to 2 malls, restaurants, parks and many local gulf coast beaches. SAFE GATED quiet community has a heated pool, gym, tennis courts and gas grills for you to enjoy. Just bring your beach blanket and swim suit and RELAX! Walking distance to so many stores/restaurants and the Pinellas trail !

Explore St. Pete! Bikes Included, Prime Spot

Tucked into a lush tropical courtyard in downtown St. Pete, the “Hideaway” is a charming and beautifully updated one-bedroom retreat full of historic character and relaxing vibes. Enjoy a queen bed, remodeled bath, full kitchen, WiFi, Smart TV, your own private pergola seating area, and two bikes exclusively for your use. Guests also enjoy access to a tropical shared courtyard with a lagoon-style pool, grills, and relaxing outdoor seating.

2 Bedroom 1 Bath Upstairs MODERN Apt NO PETS

Pools are open and wifi works great! Completely Renovated and Beautiful!2 Bedroom 1 Bathroom Upstairs unit w/t Full Kitchen. This unit sleeps 6 people. Sorry No Pets Allowed. Each bedroom has a queen size bed and the sofa turns into a queen bed as well. Watch a Movie on the 70" TV in the Living Room or Play a Game on the PlayStation 4! Or Retreat to one of the 2 bedrooms each with a 55" TV. Full Kitchen includes Stove

Cozy Couples Artsy Retreat with Local Art Walkable

Escape to Artist's Way, a cozy pet-friendly 2-BR apartment for a family or friends in St. Petersburg's vibrant Uptown arts district. This unique gallery-like space features local art, a full kitchen, a dedicated workspace, and a private patio. Enjoy a shared backyard with a BBQ, just minutes from downtown and the beaches. Perfect for couples, creatives, and small families seeking an inspiring retreat.