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Oldsmar Vacation Rentals and Hotels

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Looking for Oldsmar hotels? View all hotels in the Oldsmar area.

We have over 1300 properties in the Oldsmar, Florida area.
Please browse our top 30 properties below

Vacation Rentals in the Oldsmar/Dunedin area. (5 miles away)

	Florida Gulf Coast Bed & Breakfast Inn #214				From $155/night
	1 Beds	1 Baths	Sleeps 1-2	Bed and Breakfast
The Meranova Guest Inn offers luxury accommodations in a stylish, contemporary bed and breakfast setting, and is located in the charming quaint village of Dunedin. Fully renovated in 1998-1999, each distinctively different suite offers a private entrance, most with a porch or balcony, private bath, and ...

Vacation Rentals in the Oldsmar/Indian Rocks Beach area. (12 miles away)

	BobsFloridaBeachCondo.com Beach,HeatedPool,Tennis #2555				From $939/week
	3 Beds	2 Baths	Sleeps 6-8	Condo
Beachfront luxury condo in Indian Rocks Beach, FL (between Clearwater and Tampa/St. Petersburg) on the Gulf of Mexico available for vacation rentals, holidays, golfing adventures, romantic getaways, weddings, graduations, and corporate housing. Indian Rocks Beach is a great family beach with lots of ...


	Chic a si Cottage, directly on Indian Rocks Beach #1341				From $1,400/week
	3 Beds	2 Baths	Sleeps 6	Cottage
This cottage is directly on the Gulf of Mexico and is an Indian Rocks Beach original. Built of cypress, with vaulted ceilings, it maintains its charm with its gingerbread trim and tin roof. Stunning, large gazebo with overhead fan makes dining on the beach delightful. Haitian art and colorful hues delight ...


	Gulf of Mexico - fully furnished Beachfront Condo #563				From $900/week
	2 Beds	2 Baths	Sleeps 1-4	Condo
This newly renovated, fully furnished Gulf condo, is located on a quiet white sandy beach between Clearwater and St. Petersburg. The living room and master bedroom open onto the balcony where you can enjoy morning, noon and evening views of the Gulf and beach. There is a queen size bed in the master ...


	Original Gulf Coast cottage in Indian Rocks Beach #341				From $750/week
	2 Beds	1 Baths	Sleeps 6	Cottage
This cottage is one of the oldest original cottages in Indian Rocks Beach. "Manning Hammock" has been lovingly refurbished and has all amenities. Built by Captain John Manning in 1926, it is nestled in a hammock of live oaks and palm trees just a block from the beach, and the intercoastal waterway. ...

Vacation Rentals in the Oldsmar/Indian Shores area. (14 miles away)

	BEACH LOVERS CONDO at HOLIDAY VILLAS III #2388				From $600/week
	2 Beds	2 Baths	Sleeps 8	Condo
Completely renovated May 2008: Condo completed updated and freshly painted with new everything. New ceramic tile and carpet throughout. Most recent guests rate this unit as an A+: We dare you to compare with any other units at HOLIDAY VILLAS III. 2008 New Kitchen: New cabinets, granite countertops ...


	My Indian Shores Beach Resort Vacation Condo #1484				From $625/week
	2 Beds	2 Baths	Sleeps 4-7	Condo
Magnificent 2-bedroom/2-bathroom condominium beach vacation rental in resort oceanfront property on Indian Shores Beach on the Gulf of Mexico. Indian Shores is a unique, relaxed gulf coast community located 20 miles west of Tampa in the middle of an island with Clearwater to the north and St. Petersburg ...


	My Indian Shores Vacation Condo #1124				From $625/week
	2 Beds	2 Baths	Sleeps 4-7	Condo
Magnificent Gulf Front 2-bedroom/2-bathroom resort condominium rental on the Gulf of Mexico in the relaxed beachfront town of Indian Shores. Surrounded by warm, gentle surf and plenty to do...or do nothing but savor the relaxed atmosphere and walk barefoot on the beautiful soft, white sandy beach right ...


	Beautiful Direct Beach Front Condo #1548				From $795/week
	2 Beds	2 Baths	Sleeps 6	Condo
OUR FLORIDA GETAWAY....white, sugar-soft sands...warm waters perfect for swimming...splend sunset views over the Gulf of Mexico....dolphin, seashells, bird life, and game fish...fascinating restaurants and shops just minutes away.....here memories are made. We invite you to relax by our large heated ...


	Bayshores Yacht & Tennis Club #1592				From $400/week
	2 Beds	2 Baths	Sleeps 1-4	Condo
Vacation where you can enjoy the sun, surf & tropical sunsets. This privately owned condominium sits directly on the Intercoastal Waterway just steps away to a public beach and the beautiful Gulf of Mexico! Located in the quaint beach community of Indian Shores you can enjoy golf, shelling, tennis, ...

Vacation Rentals in the Oldsmar/Madeira Beach area. (18 miles away)

	Jan's Beach Dream Luxury Gulf Front Penthouse Cond #1562				From $1,050/week
	3 Beds	2 Baths	Sleeps 10	Condo
Our luxury Gulf front penthouse is located on the most southern end of Madeira Beach, Florida which is directly on John's Pass. Our three bedroom, two bath, luxury penthouse condo features walk-in closets, a fully equipped kitchen, breakfast bar, dining room and a large balcony overlooking the fabulous ...

Vacation Rentals in the Oldsmar/Treasure Island area. (20 miles away)

	A Whisper of Treasure Island - PRICE DISCOUNTED! #469				From $50/week
	1-3 Beds	1-3 Baths	Sleeps 1-8	Condo
Welcome to Whispers of Treasure Island, A Boutique condominium designated a "Superior Small Lodging". Winner of the White Glove Award For Excellence 2005 2006 You will be swept away by the unique charm of Whispers where every condominium has a different theme! We have two bedroom units ...


	Sunset House: Waterfront Caribbean Vacation Home #248				From $135/night, $795/week, $1,795/month
	1 Beds	1.5 Baths	Sleeps 2	House
Vacation on Florida's beautiful, Gulf Coast. Drop your anchor at Sunset House, a charming waterfront home with a tranquil waterfront patio and dock on desirable Sunset Beach, Treasure Island. Located directly on the inner-coastal within 200 feet of the white sand beaches of the Gulf of Mexico and its ...

Vacation Rentals in the Oldsmar/Zephyrhills area. (25 miles away)

	Waterfalls, Pool, Hot Tub, Secluded Victorian Home #1385				From $975/week
	2 Beds	1 Baths	Sleeps 5	House
Your private pool and hot tub are surrounded with three gorgeous waterfalls flowing over natural rocks that reach to over 10 ft. high. Pristine gardens and landscaping gracefully adorn your private designer guesthouse. You will feel like royalty while vacationing on 5 secluded acres with sprawling ...

Vacation Rentals in the Oldsmar/Sarasota area. (49 miles away)

	Sarasota 60s Modern Vacation Rental Home #400				From $2,750/month
	2 Beds	2 Baths	Sleeps 4	House
An unique property located in a desirable, centrally located, Sarasota residential neighborhood. The house is a 60's modern Sarasota ranch, decorated in period designer furniture and 60s kitsch. (Danish Modern, George Nelson, Knoll, Herman Miller, and a collection of tikis and vintage barware and dishes) ...


	VACATION RENTALS 1 BLOCK FROM BEACH IN SARASOTA #393
	1 Beds	1 Baths	Sleeps 4	Hotels
Delightful studio apartments to 3 bedroom apartments tucked away on exciting Lido Key. Nestled amid a tropical garden, the units are steps from the beautiful white sands of Lido beach, with the turquoise waters of the Gulf of Mexico just beyond. Quiet side roads and boulevards are perfect for a morning ...

Vacation Rentals in the Oldsmar/Crescent Beach area. (54 miles away)

	North Florida Vacation Rental Bungalow #204				From $400/week
	2 Beds	1 Baths	Sleeps 5	House
An ideal vacation rental in St. Augustine. Fun in the sun, Florida style! Come relax on Crescent Beach in our Cottage or Bungalow, situated on Anastasia Island, just south of Historic St. Augustine. Water, water, everywhere! You are just steps away out the front door to Crescent Beach and spectacular ...


	Crescent Beach Florida Vacation Rental #203				From $500/week
	2 Beds	2 Baths	Sleeps 6	Cottage
An ideal vacation rental in St. Augustine. Fun in the sun, Florida style! Come relax on Crescent Beach in our Cottage or Bungalow, situated on Anastasia Island, just south of Historic St. Augustine. Water, water, everywhere! You are just steps away out the front door to Crescent Beach and spectacular ...

Vacation Rentals in the Oldsmar/Haines City area. (65 miles away)

	Bethel Vacation Home #2406				From $99/night
	4 Beds	3 Baths	Sleeps 10	Villa
Looking for a rental villa or a vacation home for your Disney holiday, then look no further. Our Orlando Vacation Home located in the brand new Villa Sorrento community near Disney world is what you need. Whether you are exploring the theme parks or you just want to relax in the Florida sun, we are delighted ...

Vacation Rentals in the Oldsmar/Davenport area. (66 miles away)

	Huge Davenport Vacation home near Disney Orlando #547				From $189/night
	4 Beds	4.5 Baths	Sleeps 10	House
London UK Callers: 02079925128 This Huge 4 Bedroom 4.5 bathroom 3 Master En-sute Davenport Vacation Home villa is situated on the Hampton Lakes development complete with communal pool, Tennis courts and childrens play area. This Davenport vacation homes villas enjoys 3 master suites and is only 10 miles ...


	Davenport vacation Home w Game Room in Disney area #481				From $194/night
	4 Beds	3 Baths	Sleeps 10	House
The Sundance luxury Davenport vacation home in the very upscale Solarno Resort is waiting to welcome you through its doors and invites you to make it your Davenport vacation home for the duration of your vacation while in the Walt Disney World Orlando Florida area. The Sundance Davenport vacation ...


	Luxurious house in the Disney area w/ pool table #1093				From $189/night
	5 Beds	3 Baths	Sleeps 12	House
Our luxurious Davenport vacation home in Hampton Lakes is fit to please everyone. Fully equipped with sleeping room for up to twelve guests. Close to the Disney attractions, shopping, dining and much more. Your upscale Davenport vacation home awaits. This Executive 2 story, 5 Bedroom, 3 Bathroom ...


	Orlando Pool Villa #1533				From $650/week
	3 Beds	2 Baths	Sleeps 6	Villa
NEAR DISNEY - Just 15 minutes from all the magic and fun of Disney world - Our beautiful air-conditioned, tastefully furnished and decorated 3 bedroom / 2 bathroom villa, with private screened pool, is just the place for the whole family to relax after a long and exhausting day at the Parks.. LOUNGE The ...


	SR289 - 4BR 3BA Pool Home min. to Disney #2268				From $90/night
	4 Beds	3 Baths	Sleeps 8	House
This superb executive villa is situated in the conservation woodland of the exclusive Sandy Ridge development off CR 532 just south of Kissimmee, Orlando and just 10 minutes from the Disney attractions. The villa is fully air conditioned and equipped with everything you could wish for to make your family ...


	1160RE- 5br 3ba - Private Pool #2248				From $100/night
	5 Beds	3 Baths	Sleeps 10	House
Living Room The spacious living room has a vaulted ceiling with ceiling fan, 25' television with digital satellite cable, DVD player, access to the pool area via sliding patio door. Kitchen / Dining Area There is a lovely dining area with additional seating in the fully equipped open plan kitchen ...


	SR131 - 5 Bed 3 Bath Home with Internet #2226				From $100/night
	5 Beds	3 Baths	Sleeps 10	House
This superb executive villa is situated in the conservation woodland of the exclusive Sandy Ridge development off CR 532 just south of Kissimmee, Orlando and just 10 minutes from the Disney attractions. The villa is fully air conditioned and equipped with everything you could wish for to make your family ...


	SR642 - 4BR 3BA Pool Home with Jacuzzi #2270				From $90/night
	4 Beds	3 Baths	Sleeps 8	House
This superb executive villa is situated in the conservation woodland of the exclusive Sandy Ridge development off CR 532 just south of Kissimmee, Orlando and just 10 minutes from the Disney attractions. The villa is fully air conditioned and equipped with everything you could wish for to make your family ...


	SR321- 4 Br 3 Ba Home with Internet #2246				From $85/night
	4 Beds	3.5 Baths	Sleeps 8	House
This superb executive villa is situated in the conservation woodland of the exclusive Sandy Ridge development off CR 532 just south of Kissimmee, Orlando and just 10 minutes from the Disney attractions. The villa is fully air conditioned and equipped with everything you could wish for to make your family ...


	SR214 - Beautiful home near Disney #446				From $85/night
	4 Beds	3 Baths	Sleeps 8	House
This superb executive villa is situated in the conservation woodland of the exclusive Sandy Ridge development off CR 532 just south of Kissimmee, Orlando and just 10 minutes from the Disney attractions. The villa is fully air conditioned and equipped with everything you could wish for to make your family ...


	disney dream vacation homes #2438				From $135/night
	5 Beds	3 Baths	Sleeps 10	House
This captavating home is located in "The Palms", a subdivision of Lake Davenport Estates in the Orlando area. This stylish decorated home sleeps 2-10 people. It boasts a spacious living room, eat in kitchen, dining room. and full laundry room. There is also an inground, screened in pool with ...

We have over 1300 properties in the Oldsmar, Florida area.
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