Places to stay near Clearwater Jolley Trolley

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Top-rated holiday rentals near Clearwater Jolley Trolley

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

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Top guest favourite
Apartment in Clearwater
4.97 out of 5 average rating, 117 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 favourite
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, 193 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 favourite
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, 381 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint downtown street. Private yard with grill in prime location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's gorgeous sunsets or drive minutes to award-winning beaches such as Honeymoon Island, 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!

Superhost
Home in Clearwater
4.9 out of 5 average rating, 101 reviews

Vintage Style House minutes from the beach

Welcome to the beautiful city of Clearwater, and to our newly renovated Vintage Style duplex home. 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 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 favourite
Apartment in Clearwater
4.97 out of 5 average rating, 151 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 favourite
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, 124 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.

Guest favourite
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.
Apartment in Clearwater
4.87 out of 5 average rating, 141 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 favourite
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.
Apartment in Clearwater
4.98 out of 5 average rating, 177 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 favourite
Apartment 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.

Guest favourite
A vibrant bedroom features a queen-size bed dressed in coral linens with decorative pillows. Shelves display tropical decor, while a large mirror reflects soft light. A matching dresser and small vanity are positioned against the wall, contributing to a warm and inviting space.
Apartment in Clearwater
4.85 out of 5 average rating, 100 reviews

Avalon At Clearwater Friendly 2 Bedroom

2 Bedroom, 2 Bathroom, Sleeps 6 This apartment is on the second floor, with one flight of stairs to walk (18 steps), an 1100 sq ft two-bedroom, two-bathroom condominium unit with a fully equipped kitchen, dining area, large living room, and a patio-type balcony.Master bedroom includes a queen size bed, private bathroom with a walk-in closet and 50” screen television

Superhost
A spacious living room is furnished with a large sectional sofa and a coffee table. A 50-inch smart television is positioned on a white console. Sunlight enters through the large window covered with sheer curtains, and glass doors lead to a balcony with outdoor seating.
Apartment in Clearwater
4.79 out of 5 average rating, 169 reviews

☼ SUNNY CONDO MINUTES FROM GORGEOUS BEACHES

Hurricane Milton Update (10/10/2024): We have not been impacted by hurricane Milton. Our rental is fully functional awaiting your reservation. 1 BEDROOM / 1 BATH CONDO APARTMENT MINUTES AWAY FROM PRISTINE CLEARWATER BEACHES, WATER SPORTS, AND LOTS OF FAMILY ATTRACTIONS!!! HEATED SWIMMING POOL, GYM, FAST WIFI INTERNET, CABLE TV, NETFLIX!

Popular amenities for holiday rentals near Clearwater Jolley Trolley