
Places to stay near Clearwater Jolley Trolley
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Clearwater Jolley Trolley
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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

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.

Spacious & Fun Key West Retreat, 2 BR, Resort Pool
🌴 😎 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.

Specious home W/ Heated Pool ! ! ! Great Location.
Cozy, spacious home 🏡 w/ heated swimming 🏊♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Stop Scrolling! Cozy Home• 3BED Clearwater
MODERN HOME – 3 MILES from Clearwater Beach ✨ Fully renovated 3BR/2BA home with brand-new appliances and stylish decor! Sleeps up to 8 guests comfortably. What’s included: • Full kitchen 🍽️ • TVs 📺 • High-speed Wi-Fi ⚡ • Free street parking 🚗 • Beach chairs & umbrellas 🏖️ Located in a quiet neighborhood, just a 10–15 min drive to the beautiful Clearwater Beach! You’ve just found what you were looking for — no need to keep searching! Book your stay TODAY!

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!

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.

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!

Free parking - Heated Pool - 10 min to Beach
📍 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.

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!

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 ( only 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
Popular amenities for holiday rentals near Clearwater Jolley Trolley
Condo rentals with Wi-Fi

The Avalon-Luxe & Relax Corner Condo, Free Parking

Private Ocean View Beach Retreat with Balcony

Seaside Paradise at Clearwater - Resort Style

Cozy 1 bedroom condo.

Amazing views on beachfront

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Amazing main floor condo at Avalon

Charming Condo Minutes From Gorgeous Beaches
Family-friendly house rentals

Coastal Escape: Heated Pool, Playground&Family fun

The Oasis - Arcades - Golf & Games - HTD Pool

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Family/Group Getaway w/ Pool Near Clearwater Beach

Palm Oasis | Heated Pool | Near Beaches

Star House! Heated&Salt pool/ Clearwater Beach

Swim-Out Bedrooms, Waterfall pool, Peace Place

Hidden Oasis W Screened Heated Salt Pool / Hot Tub
Apartment rentals with air conditioning

Renovated Retreat

A cozy studio with cute garden (2mile to Beach)

Sea La Vie! 3 miles from the beach • Pets Welcome

Tropical Paradise

My Favorite Place 🍊downtown & city approved

Relaxing beach gateway

Special Price* 1 BR Apt 3 mi, 7 mins from beach

Coastal Retreat Near Madeira Beach With Game Room
Other great holiday rentals near Clearwater Jolley Trolley

Steps to Downtown, Mins. to Waterfront | Sleeps 8

Waterfront Townhome w/Game Room & Boat Slip! Walk

Clearwater Duplex Near Downtown | Minutes to Beach

Providence Cove | Heated Salt Pool • Sleeps 12

Wonderful Condo at Avalon - Fully Renovated

Pool/Work Station/Patio/Self Check In/Full Kitchen

SeaSide Condo

Designer Home | 10 Min to Dunedin Waterfront
Destinations to explore
- Anna Maria Island
- Siesta Beach
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Hard Rock Casino
- University of South Florida
- Vinoy Park
- John's Pass
- Epperson Lagoon
- Fort De Soto Park
- Tropicana Field
- Sand Key Beach
- MidFlorida Credit Union Amphitheatre
- Weeki Wachee Springs State Park
- Cortez Beach
- Anna Maria Public Beach





