
Hotels in Oldsmar
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Top-rated hotels in Oldsmar
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Beso Del Sol Resort Waterfront condo-hotel studio
Third-floor studio in the exclusive Beso Del Sol resort with spectacular views of St. Joseph's Sound and the Gulf of Mexico. Within walking distance of picturesque downtown Dunedin, with easy access to Honeymoon and Caladesi islands, and St. Andrews Links Golf Course. Elevator accessible, on-site laundry mat, gym and ample parking. Waterfront pool with heated jacuzzi. Guests can fish off the resort pier and dock their boats at the resort at a nominal fee. There is an on-site restaurant-tiki bar.

Steps to Beach, Htd Pool, Kitchenette #9
How far is the beach? Just steps away! Open the door to your perfect getaway at Boutique Beach Retreat. We are located across the street from the beautiful Treasure Island Beach and a short distance from John's Pass, where you can enjoy the pristine white sand, ocean breezes and all the adventures and activities you desire. Our guests love the warm, inviting classic Florida charm of our Boutique-Style Hotel. Come stay with us at Boutique Beach Retreat for your unforgettable beach vacation!

Charming King Suite with amazing Backyard
Deluxe King Suite (Available for Long Term)- Full Suite with kitchenette and dining area. The room is equipped with Ultra High-speed Wifi & Roku. Walking distance to Philippe Park, the Safety harbor marina, and downtown. You can enjoy daily long walks to nature, fishing, and kayaking. Philippe Park is an abode of Dolphins, Manatees, Alligators, Eagles, Owls, and ospreys. Park your large-size RV or Boat easily for free. Search Marbay motel safety harbor on the internet for direct booking.

Las Olas of Treasure Island No. 1
King Suite at Las Olas – Modern Comfort Steps from the Sand Soak up the sun and unwind at Las Olas of Treasure Island, a boutique coastal escape just across the street from the sparkling water of Treasure Island Beach. A gem of 12 clean & comfortable guest rooms designed for beach lovers. This King Suite sleeps 4 with a Queen sofabed, kitchenette and all the essentials to make you feel at home. Modern amenities with beachside charm Las Olas ~ let the waves guide you!

Downtown Tampa Stay + Historic Vibes. Bar. Pool.
Stay where Tampa’s history meets modern flair at Le Méridien Tampa, The Courthouse. Once a century-old courthouse, this unique escape now blends neoclassical style with contemporary touches. Steps from the Riverwalk, museums, and Amalie Arena, you’re perfectly placed to explore downtown. Enjoy creative cocktails at Bizou Brasserie, chill by the palm-lined pool, or unwind in your sleek, art-inspired room. A vibrant stay with a story—right in the heart of it all.

Delightful 1- bedroom suite, View of the Water
Wake up and watch the dolphins at your kitchen table!! You won’t want to leave this charming, one-of-a-kind place. The Delacado is located on the intercostal water ways of Treasure Island/ Sunset beach FL. One of the largest docks on the island for viewing the boats and marine life. If you like to fish the fishing off the dock is excellent! This Beautiful studio apartment with an efficiency is calling your name. A short walk to the beach- aprox 150 yards.

Pirate Quarters, 1 Bedroom Suite
Our newly remodeled Mid Century Modern Pirates Quarters is the Sea Jay Motel's finest suite. Bedroom includes a queen bed and 50" flatscreen/cable, living room is overlooking the canal and features a sofabed and 55" flatscreen/cable, dining room with seating for 4, full kitchen with a dishwasher, and pirate decor throughout. Suite features beautiful Terrazzo floors with tiled bathroom and tub/shower. Patio seating overlooking the canal and marina.

Clearwater Gem: 1BR Just a Block from the Beach
Charming 1 Bedroom, 1 Bath just steps from the white sands of Clearwater Beach! Perfect for a romantic getaway, weekend retreat of relaxation, beach walking, shell collecting and the most stunning sunsets in the world! Prime location in the heart of Clearwater beach close to the best restaurants, bars, and shops. Just a few blocks away is a children's playground and pickle ball courts! Everything you need for your next beach escape!

Designer King Suites at Cocktail-Themed Hotel
Spacious, stylish, and full of character — the Deluxe King Suite (269–390 sq ft) features cocktail-themed rooms like Negroni, Mule, Mojito, Margarita, Paloma, and Old Fashioned. Each suite includes a king bed, Smart TV, A/C, mini-fridge, and playful décor. Just steps from Gulfport’s waterfront and a short drive to the area’s best beaches.

Brand New! Hotel on the Marina
Be one of the first to experience this brand new boutique hotel on the marina!! With stunning views from every room, you are guaranteed to enjoy your time on the island. This beach house style hotel is the perfect vibe for your getaway. With our newly completed pool, sun deck, and rainfall jacuzzi you are guaranteed to be in paradise!

Enchanted Inn Deluxe Suite #8: Waterfront, Pool, F
This rental property is located on North Clearwater Beach on the Intra-Coastal Waterway. Located within a quick 5 minute walk to the beach & local restaurants! All rooms come with a full kitchen, a king-size bed, and loaded with all the amenities; POOL / Boat Dock / Tiki Bar

I-2 Bedroom Suite w/ Ocean View
Our suites have been curated to blend modern elements of coastal Florida style combined with the comforts of home. Each suite includes 2 bedrooms, a fully equipped kitchen, a separate living room and a private oversized balcony offering breathtaking water views.
Popular amenities for Oldsmar hotels
Family-friendly hotels

Clearwater Beach Collection / King Bed 3rd Floor

Beach Resort Oasis Awaits! – No Cleaning Fee!

Johns Pass Hotel

Oasis Palms - Premier King Studio

Hotel on the Marina with free coffee in the lobby

Vacay Deal! Walk to Beach, Dolphin Encounter, Pool

Modern Room Near The Grove | Pool, Free Parking

Across the street from the beach (public access!)
Hotels with a pool

Affordable Comfort Close to Adventure Island

Unwind in Style: Pool, Breakfast, Pets Allowed!

La Quinta Clearwater | King Room | Free Parking

Pelican Point at famous Clearwater Beach 2

Wyndham Clearwater | King Room | Marina View | Spa

Crystal Bay Hotel - B&B King

Near Clearwater Airport | Pool & Free Parking

Steps to Beach, Htd Pool, Full Kitchen #2
Hotels with a patio

Tampa Bay Double Queen 1BR w/Pool & Beach Access

3Gulls Inn5-BtqHtl-SwimSpa-Pets-KingStudio/FullKit

Stunning sunset views

Clearwater Beach Resort|1BR/1BA King Suite

Beachfront 2BR Suite @ Bay & Beach Club

Accessible Hotel Room

Ivory Sands - Standard King

Owner Suite at the Blue Bayou Inn
Quick stats about hotels in Oldsmar

Total vacation rentals
Explore 20 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at G$25,092 GYD per night before taxes and fees

Verified guest reviews
Over 10 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Oldsmar vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oldsmar rentals
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