Holiday rentals in Clearwater

Family Retreat w/Pool, Outdoor Kitchen, Near Beach

This is the Ultimate Florida rental. Relax by the pool, sit inside the screened in party room, with fridge, 55" smart TV, grill, while enjoying the best weather Florida has to offer. Located 5 miles from Clearwater beach. Every restaurant, bar, and store you could possibly want within a 2 mile radius. Baseball fans will love catching Spring Training games at Spectrum Field, home of the Philadelphia Phillies, located just a short 10 minute WALK from the house. You will love making memories here!

Location · Value · Heating

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

Family · Value · Walkability

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.

Location · Value · Bathroom

Clearwater Pool Oasis|3 BR|2 King Beds|Near Beach

Welcome to "Isa" your Clearwater retreat! This fully remodeled 3-bedroom, 2-bath private pool home features 2 king suites, a fully equipped kitchen, a dedicated workspace with a desk, and a relaxing outdoor oasis with comfortable patio furniture. Conveniently located just minutes from Clearwater Beach and charming Downtown Dunedin, you’ll enjoy easy access to award-winning beaches, waterfront dining, breweries, shopping, and local attractions while returning home to your own private escape

Check-in · Amenities · Indoor spaces

Designer Home | 10 Min to Dunedin Waterfront

Designer home 10 min to Downtown Dunedin, 15 to Honeymoon Island and Clearwater Beach. Sleeps 6: king bed, queen bed, and queen sleeper in a flex/office room. Two renovated baths with rain shower, open kitchen with large granite island, Nespresso coffee bar, and dining for 6. Private fenced backyard with covered patio lounge, outdoor dining with grill, and a second lounge under the palms. Game room with ping pong. Your home base for beaches, spring training, and the best of the Gulf Coast.

Family · Location · Decor

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.

Location · Value · Quiet

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

Family · Location · Grill

Vacation At Lantana

Come enjoy our home, whether you are coming for the beach or the theme parks our home is conveniently located in the heart of Pinellas County. With the Inter-Coastal/Gulf Waters less then a mile away, a walk or bike ride will land you at marinas, beach’s and even Honeymoon island state park. But you can also take a short car ride with your friends or family to the theme parks, airports, Big city’s, Sport venues, State parks, Camping and all the beautiful activities Florida has to offer!

Value · Location · Back garden

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

Location · Family · Air conditioning

Bday + Events • Sleep22 • Hot Pool + Projector • 10 min to the Beach

Lakefront 5BR with a half-acre fenced backyard - 10 min to Clearwater Beach: - 200" cinema screen at the pool's edge, movies over the water after dark - Heated pool, fire pit, hammock, sun loungers, lawn games - Event deck under string lights, fits rented tables and chairs - Jetted spa tub in the master: floor and side jets, LED, built-in speakers - 4 king bedrooms + a bunk room, so nobody sleeps on a pullout - Vaulted ceilings, marble tile, new AC | Pets welcome | Self check-in

Value · Family · Check-in

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.

Location · Family · Accuracy

Heated Pool, Games, Spa & 10 Min to Beach

Welcome to your ultimate Clearwater getaway — just 10 minutes from the beach and Florida’s most breathtaking sunsets! This family-friendly retreat has it all: a private heated pool, relaxing hot tub, fire pit, outdoor ping pong, putting green, arcade game, foosball, and a playground — plus a professionally designed interior with tropical-boho flair that’s as stylish as it is comfortable. This isn’t just a stay — it’s an experience your group will never forget.

Location · Family · Access