Holiday rentals with a pool in Clearwater Beach

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

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents 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.

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Waterfront Beach House Steps Away from #1 Beach!

Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee, tea and biscuits. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Renovated 2025 - Retro Beach Oasis with Color Pop

Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in -Pet friendly (One Pet max -$150 fee) We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

Beachfront Condo Resort on Treasure Island

Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

3 Bedroom Waterfront Paradise Sleeps 8

Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

Newly Reno Luxury Condo 30 Steps to Paradise

Welcome to our serene top-floor beach condo. This is a two-bedroom, two-bathroom condo in the heart of Clearwater Beach. This ocean-side condo is steps from the country's #1-rated beach and less than a five-minute walk from top restaurants and shopping. Clearwater Beach is renowned for its award-winning beaches, incredible restaurants, and lively nightlife. We have made every effort to make this condo a home away from home! We hope you enjoy our piece of paradise.

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

Cozy Retreat, private unit, NO PETS

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Walk-in distance to Publix grocery store and nearby restaurants. Location is central with short distance to nearby beaches, attractions and other nearby towns. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport and Disney World This location is loved by “snowbirds”

CWB Retreats at Baymont Lofts - Loft A

Loft A at Baymont is one block from the Sand Pearl entrance to the beach. Walk down the stairs from the spacious 2 bedroom loft, with private patio, and enjoy the local restaurants and convenient shops. Additionally, there is a queen sleeper sofa in living room. Washer and dryer in the unit is a huge perk. Full kitchen. One free, dedicated parking space per unit. 57 Baymont Street to map. New pool available at 617 Bay Esplanade you can walk to.