Holiday rentals in Pinellas County

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Top-rated holiday rentals in Pinellas County

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Guest favourite

Home in Pinellas Park

4.89 out of 5 average rating, 19 reviews

Luxury Rustic Retreat Entire Home in Pinellas Park

Welcome to your modern rustic retreat in Pinellas Park where convenience meets comfort! Perfect for families or groups, this newly renovated 2-bed 2-bath home offers everything you need for an unforgettable Florida getaway. Located just minutes from I-275, you're within easy reach of the area's top attractions from the pristine beaches of the Gulf of Mexico to world-class shopping and dining. After a day of exploring, unwind in the spacious backyard with a fire pit, hammock, and outdoor seating.

Top guest favourite

Bungalow in Oldsmar

4.98 out of 5 average rating, 122 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

Guest house in Seminole

4.96 out of 5 average rating, 196 reviews

Quiet & Cozy Guesthouse minutes to the beach.

Newly remodeled, quiet and cozy guest house on a cul de sac. Great location close to shopping/restaurants, 4 miles to Gulf Blvd where you will find many beautiful beaches, Clearwater, St Pete etc. 1 Bedroom, queen bed, and sofa bed in living room which pulls out to a queen bed. Full kitchen with all the extras. Cable TV, WiFi, 1 private parking spot (can accommodate 2 or recreational vehicle just need a heads up). Access to washer/dryer for stays 4 nights or more. No pets, no children under 8.

Top guest favourite

Guest suite in St. Petersburg

4.98 out of 5 average rating, 933 reviews

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Top guest favourite

Home in Clearwater

4.94 out of 5 average rating, 111 reviews

Best Location in Clw! Near Beach & Saltwater Pool!

PRIME LOCATION NEAR BEACH! Welcome to our newly renovated vacation home in beautiful Clearwater, FL. Located in the heart of downtown Clearwater within walking distance to several restaurants and shops and just a few mins drive to Clearwater Beach. This coastal styled home comes with a heated pool (at no extra charge), putting green, and a fun little game room for kids! The entire home is yours to enjoy and comes fully stocked with everything you need for a relaxing beach getaway vacation.

Top guest favourite

Home in Seminole

4.95 out of 5 average rating, 105 reviews

🍍Beautiful Home Heated POOL 5min to BEACH. 8 ppl🍍

Welcome to your beautiful and spacious rustic coastal-style oasis! Perfect for up to 8 guests. This immaculate updated home is located in Rustic Pines - a quiet area close to Indian Rocks Beach and the new Seminole Shopping Center. Enjoy your private backyard with a pool and luscious landscaping. Walk to shopping, dining, entertainment, and park with trails. 7 min to Largo Golf Course and only 9 min to Splash Harbor Water Park. Every effort has been made to make your vacation memorable!

Guest favourite

Cottage in Indian Shores

4.96 out of 5 average rating, 158 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Top guest favourite

Home in Seminole

4.99 out of 5 average rating, 114 reviews

Tootsie’s Beachside Retreat

LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

Top guest favourite

Apartment in Clearwater

4.99 out of 5 average rating, 96 reviews

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!

Guest favourite

Flat in Belleair Beach

5 out of 5 average rating, 19 reviews

NEW Beachfront Oasis with Beach & Pool

BEACH ACCESS a few steps away from your front door! Views of the beach included with an in-ground pool and picnic area on one of the most beautiful beaches on Florida's Gulf Coast! Our fully renovated apartment is fully equipped with a combo kitchenette, dining space, living room with smart tv, and bedroom with smart tv. If you're looking for a peaceful and fun beach getaway, you've come to the right place!

Top guest favourite

Guest suite in Largo

5 out of 5 average rating, 23 reviews

Tiny Oasis|Big Vibes|Pool&Beach!

Welcome to The Tiny Oasis! A hidden gem in Largo, FL, minutes from Clearwater and Indian Rocks Beach, this cozy retreat is packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below for full details!

Guest favourite

Flat in Clearwater

4.89 out of 5 average rating, 396 reviews

Comfy Guesthouse # 1 - 4 miles to Clearwater Beach

We would love to welcome everybody to our little spot near Clearwater Beach. You are renting 1/2 of a duplex. The other half is also being rented. The property is about 100 yards from the amazing Pinellas trail and only 3.8 miles to Clearwater beach. Downtown Clearwater is only 1.9 miles away.