Holiday rentals with an EV charger in Boca Ciega Bay

Guesthouse in St. Petersburg

4.86 out of 5 average rating, 196 reviews

Casa Magnolia- Cute and spacious remodeled unit

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. TPA is 20 mins.

4.92 out of 5 average rating, 179 reviews

Home in St. Petersburg

The Comfy Cove | Luxury Beach Getaway

Welcome to "The Comfy Cove"—where luxury meets convenience. Nestled on the most prestigious intercoastal, our 3-BR haven offers elegance just 3 minutes from the beach and 2 minutes from Seminole’s top shopping and dining. Enjoy a California king bed, 3 queen beds, ample parking, and a private yard. Perfect for beach days, fishing, golfing, or weddings, with amenities including high speed internet, Wi-Fi, Netflix, and a dedicated workstation. Experience the pinnacle of comfort and sophistication

4.85 out of 5 average rating, 137 reviews

Cottage in Madeira Beach

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!

Cottage in St. Petersburg

4.95 out of 5 average rating, 123 reviews

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.

4.99 out of 5 average rating, 120 reviews

Home in Seminole

Tootsie’s Beachside Retreat

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.

4.88 out of 5 average rating, 134 reviews

Home in St. Petersburg

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.

Bungalow in St. Petersburg

4.85 out of 5 average rating, 285 reviews

Hidden Oasis Guest Apt+Kg Bd 2bikes/close DT

Welcome to this delightful "Treehouse", a one-of-a-kind guest rental located in the heart of St. Petersburg's charming downtown/Crescent Lake area. Nestled in a beautifully renovated 1920 Craftsman property, this unique guest space features its own private entrance and bath, ensuring you have the utmost privacy during your stay. Take in the treetop views from your second-floor private patio, and relax in the comfortable king bed while enjoying your favorite shows on the Smart TV.

Townhouse in Indian Rocks Beach

4.96 out of 5 average rating, 121 reviews

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U3 ♥

✳ DAYDREAMERS ✳ This new Indian Rocks Beach condo offers convenient access to white sand beaches of the Gulf. Watch as dolphins swim into the sunset and beachcombers look for shells and buried treasure. With a coastal beachy atmosphere, this beauty will take you out of your element. This home features ultra comfy bedding for maximum rest & relaxation. So dream a little dream, while relaxing your day away. The unique coastal design compliments all of the things IRB has to offer.

Apartment in St. Petersburg

4.99 out of 5 average rating, 117 reviews

Cozy Gem Near Madeira Beach

This cozy studio unit with its own screened-in large private patio is the perfect getaway for up to 2 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cal-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 to the famous John's Pass Village and Boardwalk.

4.83 out of 5 average rating, 105 reviews

Condo in Treasure Island

Executive Oceanfront Studio

Spend your day on the nation’s top-rated beach, enjoy sunsets over the ocean from your balcony, and let the gentle sound of waves lull you to sleep in this beautiful, recently remodeled oceanfront room. This welcoming space features 2 queen beds; free WIFI, streaming services, and parking; essentials like shampoo, conditioner and body wash; kitchen with ample counter space, cooktop, and dishwasher; and incredible ocean views - everything you need to relax at the beach!

Apartment in St. Petersburg

4.78 out of 5 average rating, 252 reviews

Stay Inspired | Cozy Artist Loft, Walkable & Artsy

Whether you're writing, painting, or recharging, this creative hideaway is your personal muse. Enjoy bold, eclectic artsy décor, a cozy living space, and a full kitchen designed to inspire. Nestled in the charming Banyan Cottage near downtown St. Pete, you're steps from galleries, the Pier, and a peaceful park with a banyan tree, fountain, and ducks. Ideal for artists, adventurers, and dreamers—book your escape into color, comfort, and creativity today!