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
4.97 out of 5 average rating, 115 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, 188 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

Guest favorite
The living area is furnished with a light-colored sofa and an ottoman, offering comfortable seating. A smart TV is mounted on the wall, and a wooden dining table is visible nearby. A ceiling fan provides airflow, with natural light filtering through a nearby window.
Guesthouse in Clearwater
4.93 out of 5 average rating, 107 reviews

Adorable Vintange 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, 148 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 out of 5 average rating, 113 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!

Superhost
Home in Clearwater
4.88 out of 5 average rating, 124 reviews

Private room Clearwater

This is a private room on a residential home with private entrance and bathroom. Equipped with a small kitchenette, queen size bed(firm memory foam), Wi-Fi,smart TV, Netflix, AC, closet, and a table for two. Room has mini fridge, microwave, toaster, coffee maker, dishes and utensils. Perfect for couples. 3.5 miles, 8-12 min drive (depending on traffic) to Clearwater beach 🏖 3 min drive to Downtown Clearwater. 25-30 min drive to Tampa international airport.

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
4.94 out of 5 average rating, 105 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.

Top guest favorite
The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.
Cottage in Dunedin
4.97 out of 5 average rating, 375 reviews

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater beach, this stylish upstairs 2-bedroom cottage blends modern coastal comfort with beautiful design. Enjoy treetop views, two king beds, a sleeper sectional, and a fully stocked stay. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly with every detail beautifully done—reserve the Barefoot Parrot today.

Top guest favorite
A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.
Home in Odessa
4.96 out of 5 average rating, 125 reviews

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Top guest favorite
Condo in Clearwater
4.99 out of 5 average rating, 127 reviews

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

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, 171 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
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
4.85 out of 5 average rating, 213 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