Oldsmar Vacation Rentals & Private Rental Homes.

Condo in Oldsmar

In Oldsmar, located near Tampa, Dunedin, Palm Harbour, Clearwater and St Petersburg.This ideal location is minutes from the Bay and just 20 minutes from the beautiful beaches of the Gulf of Mexico. The waters of Tampa Bay, the Gulf and Lake Tarpon combine to make these an area of unparalleled recreational and leisure time activities.
This second floor recently renovated condo is located in the premier community of East Lake Woodlands Country Club. This is a large gated community encompassing .......

4.8 Star Review

Apartment in Oldsmar

Stunning newly furnished, larger condo located in East Lake Woodlands, nestled off the 18th hole of the North Course. This beautiful 2 bedrooms / 2 full baths, with an open flex space for family room or den, has an abundance of space and amenities including a 1 car attached garage. The kitchen is a cook's dream, including a large granite island with flat cook top, extended counter space for bar stools, wraparound granite counter tops and cabinets with the upgraded appliances and an eat in breakf.......

Studio - Sleeps 2
Vacation Rental in Oldsmar

Condo in Oldsmar

STUNNING FULLY FURNISHED RENTAL AVAILABLE MAY 1, 2022. LOCATED IN THE GATED COMMUNITY OF EASTLAKE WOODLANDS. JUST BRING YOUR TOOTHBRUSH TO THIS WONDERFUL CONDOMINIUM. WOODLAKE RUN IS WHERE YOU WILL FIND A BEAUTIFUL FULLY FURNISHED 1ST FLOOR 2 BEDROOM 2 BATH CONDO WITH LAKE VIEWS AND COASTAL DECOR. A 1 BEDROOM UNIT LOCATED ADJACENT MAY BE AVAILABLE FOR LARGER FAMILIES/MULTIPLE COUPLES. THIS UNIT IS ONE OF THREE UNITS LOCATED IN THE SAME BUILDING - CALL FOR AVAILABILITY. LIVING ROOM FEATURES SCENI.......

2 Bedrooms - Sleeps 4
Vacation Rental in Oldsmar

Condo in Oldsmar

AVAILABLE 4/1/2022.SHORT TERM FULLY FURNISHED RENTAL WITH ALL UTILITIES, CABLE AND WI FI INCLUDED!! JUST BRING YOUR TOOTHBRUSH TO THIS WONDERFUL CONDOMINIUM. OUTSTANDING GATED , GUARD ATTENDED 24/7 COMMUNITY OF EAST LAKE WOODLANDS IS WHERE YOU WILL FIND A BEAUTIFUL FULLY FURNISHED 2ND FLOOR LAKEFRONT 1 BEDROOM CONDO FEATURING UPDATED FURNITURE WITH COASTAL DECOR.LIVING ROOM FEATURES SCENIC WATER VEIWS, SOARING CEILINGS, 40 IN HIGH DEFINITION SMART TV WITH BLUE RAY DVD PLAYER, WI-FI INTERNET ACCE.......

1 Bedrooms - Sleeps 2
Vacation Rental in Oldsmar

Private Vacation Home in Oldsmar

This is a beautiful and spacious home, located in Oldsmar, Pinellas County , Florida.
It is perfect for family vacation or romantic get way, it is single family home with 3 bedrooms 2 bathrooms 2 car garage .
it is minutes driving to the beaches , shopping and entertainment, walking distance to fine restaurants but still tucked way so very quiet, the neighborhood is very friendly and safe !

Only 11 miles to Honeymoon Island State Park an 30 minutes to Clearwater Beach
walking di.......

4.9 Star Review

Private Vacation Home in Oldsmar

WE WANT YOU TO FEEL AT HOME!

This is a BEAUTIFUL and VERY CLEAN home that has been recently renovated and is located in a private cul de sac, in a very safe and quiet community.

2 Bedrooms (Queen size beds)
2 Full Bathrooms
Eat-in Kitchen w/ updated appliances
Living Room with High Ceilings
Washer and Dryer
2 Car Driveway with Garage

House is equipped with central air conditioning and ceiling fans. The house will be nice and COLD!

The kitchen has gra.......

4.8 Star Review

Private Vacation Home in Oldsmar

Beautiful 4 bedroom, 2 bathroom single family home tucked away on a quiet CUL-DE-SAC , close to fine restaurants , beaches, parks , cinema and shopping malls
Large living room , gas barbecue grill, fire pit, 3 blocks to Sheffield Park.......

5.0 Star Review

Private Vacation Home in Oldsmar

LIKE NEW! Contemporary house located in Oldsmar close to beaches, restaurants, shopping, Safety Harbor & Dunedin! 2 Blocks from SPONAUGLE WELLNESS!

3 Bedroom 2 Bath with large 2 car garage built in 2016.
This new home features: porcelain tile floors, stainless steel appliances, window blinds, granite counter tops with wood kitchen and bathroom cabinetry, 55" HD flat screen TV, all new furniture, full sized washer and dryer, ceiling fans.
* Master features a king-size bed, with ext.......

4.7 Star Review

Condo in Oldsmar

Beautiful Fully furnished ground floor holiday home to rent in Oldsmar, Tampa Florida.
This really is a home away from home set in the gated community of East Lake Woodlands.
This Condo is located just minutes away from Shops, Cinema, Golf Course, Restaurants and Coffee Shop which are all within walking distance.
Tampa Airport is just 14 miles away and Busch Gardens just 19 miles.
The world famous Clearwater beach is located just 15 miles away.
There is a 36 hole golf course loca.......

4.9 Star Review

Villa in Oldsmar

This is a beautiful 3 Bedroom Villa in the Quail Forest Area of East Lake Woodlands.

This fully equipped Condo/Villa is all on one floor and has an open and easy living floor plan.

The unit overlooks a pond full of wildlife and those interested in relaxing and bird watching will love the view either from the enclosed lanai area or the outside patio on the chaise lounges and chairs.

The unit has covered parking for your vehicle and is conveniently located close to any shoppin.......

4.1 Star Review

Private Vacation Home in Oldsmar

Three bedrooms, two baths with a loft area. Large fenced-in yard and huge driveway with additional parking across street. Recently fullly renovated with newer furniture and appliances. A beautiful patio area in the back yard with a fire pit and grill. Walking distance to bay, zip lining, tennis, basketball, pickle ball, biking and hiking trails, eateries, and a 5 min drive to a small private beach area. Honeymoon Island is just 11 miles away and you are centrally located to Tampa, St. Pete, C.......

3 Bedrooms - Sleeps 5
Vacation Rental in Oldsmar

Private Vacation Home in Oldsmar

Your home away from home. This house has been completely renovated with you in mind. Lots of privacy palms line the property and there's a huge deck off the kitchen to enjoy your morning coffee or evening wine. The inside has brand new tile throughout, two stunning new bathrooms, two queen bedrooms and the third bedroom is setup as an office or workout room. Kitchen is fully equipped and ready to cook all your favorite meals... or not - because we have plenty of great restaurants within a few mi.......

5.0 Star Review

Private Vacation Home in Oldsmar

Located in Oldsmar, this welcoming vacation home brings it all within your reach. Jump into your car and make short work of the 4-minute drive to Tampa Bay or the 4-minute drive to Chi Chi Rodriguez Golf Club (and enjoy the property's convenient covered onsite parking in the meantime).

This vacation rental features a BBQ grill and air conditioning. Enjoy the free WiFi and cable/satellite TV. Bathroom amenities include a hair dryer, towels, and shampoo. Prepare a home-cooked meal in the.......

4.7 Star Review

Villa in Oldsmar

Relax in this quaint, fully-furnished villa in a safe, quiet neighborhood. The backyard sits on a nature preserve, providing privacy, plenty of trees, foliage and bird watching. Close to parks, bike trails, tennis, disc golf, and more. Separate full laundry room available. Two queen beds. Parking in driveway and off street parking. Perfect blend of quiet, tranquil home in a great location that’s close to everything!

Fully equipped kitchen. Large patio including screened porch. Patio wit.......

4.9 Star Review

Private Vacation Home in Oldsmar

Gorgeous upscale 3/2 Home, centrally located in Tampa Bay. Breathtaking backyard with private pool and bbq area, beautiful front yard with garage and street parking. 9 minutes from Honey Moon Island, 20 minutes from Clearwater Beach, 6 minutes from Safety Harbor and Dunedin, 15 minutes from Tampa International Airport, 25 minutes from Ybor City , 30 minutes from Hard Rock Casino, 35 minutes from St. Pete, 40 minutes from Busch Gardens and Island of Adventure!!.......

3 Bedrooms - Sleeps 6
Vacation Rental in Oldsmar

Condo in Oldsmar

NEW- Waterview- 2 bed/2 bath condo w/pool
This 2 bed 2 bath condo is located in a quiet peaceful golf course neighborhood yet minutes from shopping & AMC theatre!
Enjoy amazing sunsets and wonderful water view of large pond from the spacious balcony. Pool is just steps away from condo. Honeymoon Island Park 8 miles, beaches 16 miles. Enjoy your stay w/ complimentary wifi & many other amenities! Please let us know how to make your stay as comfortable as possible. Message w/ any questions we.......

5.0 Star Review

Private Vacation Home in Oldsmar

*****AVAILABLE TODAY - (November 17, 2023) - BOOK NOW!!!
5⭐⭐⭐⭐⭐ Service & Accommodation

Welcome to our stunning waterfront retreat with a million-dollar view!

Nestled in a peaceful cul-de-sac on Oldsmar's picturesque Waterfront Shore Boulevard, this elevated home offers a truly extraordinary experience.

Boasting a half-acre of land, this unique property commands panoramic vistas of the glistening Tampa Bay waters.

Prepare to be captivated by the 165 fee.......

4.0 Star Review

Private Vacation Home in Oldsmar

Are you looking for a staycation or vacation close to the beach and Tampa?

Welcome to Hibiscus Haven! This adorable and DOG FRIENDLY home is renovated with a newly refinished pool and deck and brand new furniture! The home is comfortable for 4 people in two private bedrooms but there's enough room to sleep up to 10 including the sofa beds!!!

We offer the comforts of home by providing all you need to have an enjoyable vacation including all bedding, towels and the kitchen is fu.......

4.7 Star Review

Apartment in Oldsmar

Explore bike trails, waterfront parks, local beach and even ziplining, within walking distance of your suite! Central to all of Tampa Bay.

Quiet bedroom suite & large fenced patio with private hot tub and lounge chairs. Relax in queen bed with Smart TV, controllable AC/heat/fan, microwave, mini-fridge, coffeemaker & organic coffee, recliner and room-darkening blinds.

Keep the Florida experience going with your private outdoor shower. NOTE-the only shower is outside-fully surrounded.......

5.0 Star Review

Private Vacation Home in Oldsmar

Relax with the whole family at this peaceful newly renovated place to stay. Only a short drive to all Tampa Bay attractions!
Places of interest that are around the area are:
-Honeymoon island where it is home to sandy beaches, trails, and an abundance of wildlife.
-The Sponge Dock in Tarpon Springs where it is popular for it's historic buildings and where there are Greek restaurants, art and culture.
-One of the most famous beaches in the US is Clearwater beach which it is ab.......

5.0 Star Review

Private Vacation Home in Oldsmar

Perfectly located 20 mins to airport ,beach and Raymond James Stadium and walking to shopping area ,movies enjoy the outdoor with swimming pool 2 grills large patio ,pool table ,parking to fit an RV or a Boat .......

4.9 Star Review

Private Vacation Home in Oldsmar

Escape to paradise at our Tropical Vacay bohemian home with a private pool, nestled in the heart of Oldsmar, Florida. This enchanting retreat offers an unforgettable experience for those in search of relaxation, outdoor excitement, and a blend of bohemian-modern aesthetics with cozy charm.

With 3 bedrooms and 2 1/2 bathrooms, this property provides the perfect oasis for your vacation. The highlight of your stay will undoubtedly be the inviting pool, where you can bask in the Florida sun o.......

3 Bedrooms - Sleeps 10
Vacation Rental in Oldsmar

Private Vacation Home in Oldsmar

Pack your sunscreen and get ready for a Gulf Coast getaway at this 3-bedroom, 2-bath Oldsmar abode! Boasting a prime location and all the conveniences of home, this vacation rental is the ideal place to return after all of your Sunshine State adventures. Soak up the sun at Mobbly Bayou Beach Park, shop local at the Oldsmar Flea Market, or spend the day in downtown Tampa. When you need a break from exploring, take a refreshing dip in the plunger pool or fire up the gas grill for a family cookout........

4.0 Star Review

Private Vacation Home in Oldsmar

This amazing and spacious 5 bedroom home is located in a prime neighborhood of Tampa, offering plenty of room to relax and entertain your guests!

The luxurious game room features a ping pong table, perfect for exciting nights with family and friends.

Enjoy movie nights in the comforts of your home, or cook up large delicious dinners for your guests in the fully-equipped kitchen.

Experience luxury living in Tampa by booking this exceptional 5-bedroom home – with a minimu.......

5 Bedrooms - Sleeps 16
Vacation Rental in Oldsmar

Apartment in Oldsmar

About this space
New, private, family friendly attached apartment by the shores of Mobbly Bay in Oldsmar, FL. Located in a fantastic area few minutes walk from parks and trails with stunning water views and at short distance of many of Tampa’s and Pinellas’ attractions, restaurants and shops. It features 1 bedroom with a queen size bed, a full bath, private patio, and living/dining and kitchen room. There is a small sofa bed in the living room and kitchen its equipped with everything you .......

5.0 Star Review

Condo in Oldsmar

With all the commodities and coziness of home you will thoroughly enjoy your vacation in this condo. It is fully equipped with a washer and dryer for your convenience. Nestled in the quite tranquil setting of East Lake Woodlands, this condo is centrally located with easy access to Tampa International airport, movie theater, shops and dinning. Conveniently near state parks and beaches. Just a short 30 minute ride to Busch Gardens........

4.9 Star Review

Private Vacation Home in Oldsmar

Enjoy a quiet stay in our beach guest home specifically designed for our AirBnB guests. 3 bedroom/2 bathroom/ 2 car garage home located across the street from wilderness preserve with quiet beaches, trails, picnic areas, zip lining, kayaking, tennis & basketball courts, playgrounds and more. The location is a gem, centrally located to Tampa, Clearwater Beach and St. Petersburg all within approximately 35 minutes drive. Orlando trip is under two hours. There is so much to do and see nearby.
Th.......

5.0 Star Review

Apartment in Oldsmar

Beautiful and well kept 2 bed apartment located in gated community of East Lake Woodlands. Quiet neighborhood with shared pool with sun loungers, umbrellas, public toilets and childrens pool toys. Comfortable living space with master bedroom with En-Suite and twin room with adjacent bathroom. Full service kitchen for cooking meals and own washer and dryer on-site. Located within walking distance to local bars, restaurants, cinema, shopping and grocery stores. Located 40 mins from Clearwater beac.......

2 Bedrooms - Sleeps 4
Vacation Rental in Oldsmar

Condo in Oldsmar

Eastlake Woodlands first floor condo with 2 split bedrooms , 2 full baths, one with tub and one with walk in shower, living room and dining room combo. Full kitchen. Plenty of closets. Covered patio and rear water view screened lanai. Full size washer and dryer. Up to two small dogs allowed with a nonrefundable pet fee of $300. IMAX theater, concert hall, gulf beaches, sports arenas and public golf courses abound. .......

4.6 Star Review

Villa in Oldsmar

This is a fully equipped 3 bedroomed Villa in the popular Quail Forest area of the gated East Lake Woodlands community.

All on one floor , it has an open and easy floor plan with the benefit of a great room with a cathedral ceiling. There is a separate dining area with wet bar to the kitchen and an enclosed lanai.

The unit faces due north and receives the morning sun into the kitchen. The living space overlooks ponds full of wildlife with a 180 degree view. Those interested in r.......

3 Bedrooms - Sleeps 8
Vacation Rental in Oldsmar

Apartment in Oldsmar

Ever live in a tiny home? Well here's your chance to try it. Fully equipped kitchen with granite countertop and full size stainless appliances. Propane gas stove and gas instant hot water heater. Ample size bathroom with granite sink top and good size jacuzzi tub. Large, mirrored wardrobe closet. Queen bed in loft. And futon on main level. Large deck out front with patio furniture to enjoy morning coffee and listen to the birds and wood peckers.

Located close to both airports (TPA and PIE.......

1 Bedrooms - Sleeps 2
Vacation Rental in Oldsmar

Private Vacation Home in Oldsmar

3300 square foot modern home in Tampa Bay Area with resort style pool. 4 bedroom, 4 Bathroom bonus loft. Includes 3 queen beds and 1 king bed ( Master ). The back of the house faces west so you get sun on the pool deck all day long.

Centrally located - 15 miles to Clearwater Beach, 10 miles to Raymond James Stadium, 9 miles to Tampa International Airport. Quiet neighborhood surrounded by parks, restaurants, Golf, Tampa Bay Downs. 6 Tv's, wifi, full kitchen. Perfect spot to host a group. .......

4.9 Star Review

Private Vacation Home in Oldsmar

Experience the epitome of Florida living in this stunning three-bedroom, three-bathroom townhouse nestled in a secure gated community in Oldsmar. Immerse yourself in the charm of this spacious residence, complete with a private tennis court and a sparkling swimming pool. Boasting modern amenities and stylish finishes, this home offers a perfect blend of comfort and elegance. Don't miss the opportunity to own a piece of paradise in this sought-after location........

3 Bedrooms - Sleeps 7
Vacation Rental in Oldsmar

Apartment in Oldsmar

View the interactive property! | Stunningly renovated 3Beds / 1Baths home with 1-car garage located in relaxing Oldsmar. This home features a beautiful driveway as you arrive to it, with a vivid front yard. Upon entrance, you will find an open layout, with great circulation between the common areas and bedrooms. Tons of natural light from every corner. The roof is in great condition, Windows are in great condition, HVAC is in great condition, NEW bathroom with nice modern details, NEW floors, NE.......

3 Bedrooms - Sleeps 6
Vacation Rental in Oldsmar

Condo in Oldsmar

GOLF COURSE VIEW Move in Ready Large Spacious 2nd Floor Condo with Carport. New Roof in July of 2021. This END unit offers more privacy, extra windows and a Wood Burning Fireplace. The condo features Newer Laminate Flooring in the living area and Shag style carpet in the bedrooms, and tile throughout in kitchen and bathrooms and a Stainless Steel Refrigerator. The guest bathroom has been updated. The Master Bedroom has 3 walk in closets. Plus there is a storage closet on the back screened lanai........

2 Bedrooms - Sleeps 4
Vacation Rental in Oldsmar

Private Vacation Home in Oldsmar

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage that can fit two cars 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.
Th.......

5.0 Star Review