Places to stay near Clearwater Jolley Trolley

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Top-rated vacation rentals near Clearwater Jolley Trolley

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Condo in Clearwater
4.98 out of 5 average rating, 120 reviews

Lovely Condo minutes from beach & King bed

Kick back and relax in this calm, stylish space.Minutes away from Clearwater Famous Beach.You will be pleased with high ceilings and open floor plan.King size bed in the Bedroom with balcony and 55" smart Tv. Walk-in closet and updated bathroom. Spacious covered patio style balcony. Full-size washer and dryer inside the unit. Fully updated and equipped kitchen. Specious living room with a sleeper sofa that can sleep two quests and 65"smart Tv. Heated outdoor pool, gym, fast wifi internet, cable

Guest favorite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.95 out of 5 average rating, 198 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top guest favorite
A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.
Cottage in Dunedin
4.99 out of 5 average rating, 389 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in terrific location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's stunning sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

Guest favorite
Guesthouse in Clearwater
4.93 out of 5 average rating, 112 reviews

Adorable Vintage Style guest house | King size bed

Welcome to the beautiful city of Clearwater, and to our newly renovated Vintage Style Guest house. Conveniently located within 0.5 miles or 7 minutes walking to clearwater downtown, and 3 miles or 7 minutes driving to the famous and award winning Clearwater beach. Easy access to local restaurants, bars, stores, and parks. This comfortable guest home features unique layout with Vintage-modern decor, free WiFi, smart TV, LVT flooring and sleeps up to 4 people. It also offers one free parking.

Top guest favorite
Condo in Clearwater
4.97 out of 5 average rating, 155 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory Foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts. Enjoy beach 🏄‍♂️ vibes decor in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Top guest favorite
A peaceful outdoor area is surrounded by lush greenery, featuring palm trees and vibrant plants. A simple table and chairs are positioned beneath a canopy, providing a shaded space for relaxation. A whimsical flamingo decoration adds a playful touch to the serene environment.
Guest suite in Clearwater
5.0 out of 5 average rating, 136 reviews

Clearwater Studio Getaway

Welcome to Clearwater Studio Getaway! Enjoy a peaceful and centrally-located space just 15 minutes from Clearwater Beach, Downtown Clearwater, and the Tampa Bay área .Just 7 minutes from Safety Harbor and 14 minutes from Dunedin . Perfect for travelers or couples, this cozy studio features a private bathroom, comfy bed, and essential amenities. Relax after a day of sun and fun, with shops, dining, and attractions all within easy reach. Your perfect Florida stay!

Top guest favorite
A welcoming entrance to The Avalon features a landscaped roundabout with manicured greenery and vibrant flowering plants. A central fountain adds a serene element, while the building's architecture is framed by palm trees and blue skies.
Condo in Clearwater
4.95 out of 5 average rating, 110 reviews

Condo Conveniently located to Clearwater Beach

Located close to the beautiful white sand popular Clearwater Beach, with an on-site heated pool. Unit is located on the bottom floor for easy access. This condo is close to shopping and restaurants. Fully stocked kitchen, washer and dryer and everything you need for a perfect stay. There is free wifi, 130 channels of cable TV channels, Hulu and Netflix. King size comfortable bed, enclosed balcony and full access to the gym and club house with free parking.

Guest favorite
The exterior of a two-story condo building is featured, surrounded by tropical palm trees and well-maintained greenery. A paved walkway winds through the landscape, leading to the entrance of the building. The facade includes large windows, allowing natural light to fill the interiors.
Condo in Clearwater
4.86 out of 5 average rating, 144 reviews

Cozy 1 bedroom condo.

Enjoy Clearwater from this beautiful 700 SFT, 1 bedroom condo with year-round access to a heated pool and only a 15 minute drive from Clearwater Beach. 2nd story condo with a single flight of stairs not shared by any other apartments. Safe and quiet gated community. Gym next to the pool. Parking is unassigned with plenty of spots next to the buildings. Beach chairs, umbrella, towels, cooler and other items available for your use.

Top guest favorite
A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.
Condo in Clearwater
4.98 out of 5 average rating, 180 reviews

Ocean Breeze • Easy - Heated Pool Access

📍 Stay in The Avalon at Clearwater, a gated community with a heated pool, fitness center, clubhouse, and free parking. Walk to Publix, restaurants, cafés, and shopping. Just 15 minutes to Clearwater Beach, 20 minutes to Tampa Airport, and convenient to Dunedin, Safety Harbor, Honeymoon Island, St. Petersburg, and other top Gulf Coast attractions. Perfect for beach getaways, business travel, snowbirds, and extended stays.

Top guest favorite
Condo in Clearwater
4.94 out of 5 average rating, 110 reviews

Hmmm...Peace and Tranquility! Just Relax!

30 min from Tampa International Airport and in 15 minutes from St Pete International Airport, you get to this Location. The resortlike complex, is only 3 miles away from beautiful Clearwater Beach which has been consistently and constantly rated as one of the Best Beaches in America. We hope you and your loved ones make joyful memories filled with laughter, memorable moments, a restful and safe vacation at our place.

Top guest favorite
A modern bedroom features a spacious bed with grey upholstery and decorative pillows. Two bedside tables with lamps are positioned on either side of the bed. Framed artwork hangs above the bed, and a stylish table is placed nearby, accentuated by a small plant.
Guest suite in Clearwater
4.92 out of 5 average rating, 294 reviews

Home away from home!

Enjoy a comfortable private studio in Clearwater, perfect for up to 3 guests. Features a queen bed, sofa bed, private bathroom, fully equipped kitchen, Netflix, and free private driveway parking. Relax in the private fenced courtyard, where smoking is permitted. Located approximately 5 miles from Clearwater Beach, close to restaurants, shopping, and entertainment. Thoroughly cleaned after every stay!

Top guest favorite
A spacious room is highlighted by a large bed with a geometric patterned comforter. A desk with a chair is positioned next to the bed, accompanied by wall decor and a standing mirror. Light from a window illuminates the area, creating a welcoming environment.
Apartment in Clearwater
4.86 out of 5 average rating, 219 reviews

Beautiful studio with cute garden (2mile to Beach)

This is a wonderful studio in the beautiful city of Clearwater. Within a few mins driving or biking distance to the famous Clearbeach, you'll enjoy the gorgeous sunset ocean view. Easy access to local restaurants, bars, and stores. No matter you just want to chill out in the sunset or attend the concern in Coachment Park, this studio will be your perfect choice.

Popular amenities for vacation rentals near Clearwater Jolley Trolley