Holiday rentals with outdoor seating in Clearwater

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

NEW! High End King Mattress! 10 Steps to the beach

AMAZING LOCATION! Located within crawling distance of the sugary white sands of the world famous Clearwater Beach! Equipped with a Premium King Casper Wave Hybrid Snow Mattress which retails at $4,000, to ensure an amazing nights sleep. Located in a small building with just 6 units, only 1 house from the beach. Walking distance to practically everything in town including many great restaurants, bars, shops, Pier 60, the marina & more, yet still located on a quiet street. No car is necessary!

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Relax in this renovated waterfront apartment. Unwind after your day at the beach on the patio overlooking the sun setting over the water. This fresh space has everything you need for your stay; a full kitchen stocked with cooking supplies, two full bedrooms & bathrooms, a large living area with ocean views to name a few highlights. Only 5 miles to the #1 rated Clearwater Beach, 1.3 miles to the fun Downtown Dunedin, a block to the Pinellas Trail, & 1 mile to the Blue Jay’s stadium!

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

Hidden Oasis #3 BIKES&BEACH *renovation discount*

*Renovation discount! We are redoing the yards. Dining table and seating & the grill/smoker are still available!* Walk into this welcoming apartment and find your paradise! This cozy, private space is found tucked away from the rest, facing its own patio and yard area. Enjoy shared access to a larger courtyard w/ grill & smoker. Short 10-minute drive to the best world-famous Gulf beaches. FREE BIKES & TONS OF BEACH SUPPLIES. Come make yourself at home in this Hidden Oasis 🌴

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.

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.

Luxury Beach Bungalow | Walk to Dining & Sunset

Welcome to Mango! Nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits! 🥭

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!