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Oldsmar Rentals

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1,652 Houses

Dolphin Bay Retreat

Oldsmar house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$287

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 16 minutes

Price per night from

$132

Florida Blue House

Oldsmar house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$182

WanderJaunt | Rocco | 1BR | Town N Country

Oldsmar studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 20 minutes

Price per night from

$11,403

Price per night from

$321

Serenity Suite near Tampa's Reigning NFL Superbowl Champion and NHL Stanley Cup

Oldsmar apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

La Rustic House

Oldsmar house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$389

Great rentals within 20 miles that match your search

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 1 minutes

Price per night from

$130

Lakeside Apartment Near Clearwater Beaches

Palm Harbor apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$79

Surfside Condos 204 Beachfront Condo

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 10

“Surfsude Condo 204” The view was great....the condo was roomy enough for our family. Everything was good except needed more instruction on using TV in living room. Also needed more electrical outlets. We would stay here again. Had a great time.

Price per night from

$735

Bay Breeze House Waterfront home with pool

Clearwater house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$290

HIstoric home/apartment in the Heart of Tarpon Spr

Tarpon Springs apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 44 minutes

Price per night from

$149

*NEW* Spa Retreat: Relaxing Pool Home w/Hot Tub, Amenities and Conveniences

Tampa house

4 bedrooms / 3 bathrooms / sleeps 6

“Amazing Stay! Abolutely Loved This House!” My friends and I travel every year following our favorite football team and often look for homes to rent that provide many of the amenities you might find in high end hotels. In this home we found a gem. Property is amazing...well kept, spacious and convenient. Working with Paul was awesome and very welcoming. During the stay, Paul was always available at a moments notice if you needed anything. The home provided plenty of room for our group and the pool and spa are an extra added bonus. We were convenient to the highway, grocery stores and even Wal-Mart and restaurants. I will certainly look forward to staying in this property again when my travels bring me back to Tampa! Hats off to Paul and his team. Amazing Property!

Price per night from

$285

3BR/2BA Beautiful Beach Location

Indian Rocks Beach apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Amazing location, just perfect!” The location of this condo is absolutely perfect. Access to the beach, lots of little shops, restaurants near. Nice pool to enjoy when you are not on the beach. It was clean and super nice to have a washing machine and dryer available. Went home with clean clothes! Would definitely recommend this to friends and family, and hope to go back sometime!

Price per night from

$228

Desirable Resort Style Condo in Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$86

Beautiful waterfront apartment with stunning views

Madeira Beach apartment

1 bedroom / 1 bathroom / sleeps 2

“Brilliant location and very friendly hosts.” This is a condo with a kitchen/diner and lounge area downstairs and a bedroom (and very comfy bed) and bathroom upstairs. There is a balcony outside the bedroom, which faces east so you have the beautiful sunrise. The condo is well equipped, and you have the use of the pretty patio/garden at the rear which is right on the intracoastal and which is shared with the hosts. There is the usual abundance of wildlife including dolphins, and a very pretty outlook. The beach is three or four minutes walk away, along with local shops and restaurants. We loved our stay there and would certainly go back. The hosts are very friendly and amenable.

Price per night from

$119

Clearwater Beach Waterfront #19. 2 Queen beds! Walk to all the fun!

Clearwater apartment

/ 1 bathroom / sleeps 4

“Cozy” Great condo. Close to the beach. Very clean. Has everything you could possibly need for the perfect Clearwater Beach vacation.

Responds fast! avg. 55 minutes

Price per night from

$143

3 bedroom, 2 bath home, just steps to the beach

Treasure Island house

3 bedrooms / 2 bathrooms / sleeps 6

“What a great week we had” We recently had a family reunion at this beach house. There were eight of us and there was plenty of room. The house was a wonderful place and we really enjoyed morning coffee around the island in the kitchen and s'mores in the evening on the back deck around the fire pit. Several times we grabbed a glass of wine and walked to the beach to watch the sunset and even saw a few dolphins. The area seemed to have a lot of events happening nearby, sand sculptures on the beach, shopping at a restored fishing village with several unique shops, bands on the sands and fireworks. The oversized wrap around deck added extra room to what already felt like a spacious house. The house is beautiful and we look forward to vacationing there again.

Price per night from

$457

Tampa TreeHouse

Tampa house

3 bedrooms / 3 bathrooms / sleeps 10

“Perfect Vacation Home!” This is the perfect vacation rental!! Clean, comfortable and well furnished. Close to beaches, entertainment and dining. The owner has all the bases covered and goes the extra mile to help with anything you need. I highly recommend this property for your vaction and am already planning our 2015 stay! Thanks again Javier!

Responds fast! avg. 3 hours 53 minutes

Price per night from

$421

Waterfront Home away from Home

Dunedin apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 51 minutes

Price per night from

$114

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Exceptional” We just returned from a 4 week stay at another/similar condo in this same building, same owner. The unit was clean, comfortable, spacious and located in close proximity to everything we needed (i.e. Beach, supermarket, restaurants, shops). John (owner) was more than accomodating with helping us get online (wifi) and being flexible with our schedule. The Gulf view was great and the building was relatively quiet considering it was Spring Break month. Will definitely be returning.

Price per night from

$239

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

Price per night from

$284

"Something Fishy" Beach Front Condo & Sunset Views

Indian Rocks Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$177

Sea Breeze 108 (Madeira Beach) COVID Discounts Winter 2020-21

Madeira Beach apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$228

Clearwater Beach Furnished Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$162

* Busch Gardens " Welcoming & Comfortable"

Tampa house

3 bedrooms / 2 bathrooms / sleeps 9

“Sunshine State Vacation Well Done!” We had an amazing time in this lovely Florida rental. I would highly recommend this place for families with kids. The house is clean and conveniently located near many fun things to do. Disney is only hour and fifteen minutes away which made easy for one day visit to Magic Kingdom! Host was friendly and resourceful. He was quick to respond to all of our questions and he offered advice on many great things to do in the area!

Price per night from

$280

Beautiful Beachfront Condo on the FL Gulf Coast

Madeira Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful family beach vacation condo” The condominium is a great place to stay. All the amenities you need to enjoy a relaxing family vacation. There is an picturesque view of the beach on the balcony and a large pool to enjoy. The location of the condo is convenient to shopping and restaurants. Carol (the owner) is always very helpful and accessible if you have any questions about your stay. We have found a new place to stay on our summer vacation and can't wait to visit again next year!

Responds fast! avg. 3 hours 32 minutes

Price per night from

$195

Indian Shores Condo

Indian Shores apartment

2 bedrooms / 2 bathrooms / sleeps 6

“clean wonderful and quite” T\his is the second year we have rented this gem We are looking forward to many more years of renting this unit.

Price per night from

$98

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$478

Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome

Treasure Island condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 16 minutes

Price per night from

$540

Waterfront Penthouse Condo on Intercoastal Across from Beach

Indian Shores condo

2 bedrooms / 2 bathrooms / sleeps 6

“Great views” Great place in a good location and awesome views of the intercoastal. Enjoyed sitting on the patio and watching the boats go by. Would definitely stay there again if i am in the area.

Responds fast! avg. 2 hours 40 minutes

Price per night from

$223

Cove Cay Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 16 minutes

Price per night from

$54

Perfect Vacation Townhouse With Gulf View

Indian Rocks Beach house

3 bedrooms / 4 bathrooms / sleeps 8

“Best house on the beach!” We will never forget our memories on Indian Rocks Beach! We wish we lived here, and could wake up every morning to the views and the ocean. The beach is only steps outside the back patio doors, with no tourists and crowds. It feels private, with sea-turtle nests, and sunsets just for us! The house is huge, spacious, and well-equipped with everything we needed! The owners take great pride in making it special for guests, with restaurant recommendations, etc. We can't wait to go back! Thanks for the memories our kids and I won't soon forget.

Price per night from

$213

beautiful condo with magnificent views of mandalay

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$152

Wonderful Belleair Beach Condo

Belleair Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$97

Oceanfront 1400 sq ft Condo at Beach Cottage One! Private Beach, Big Pool

Indian Shores apartment

2 bedrooms / 2 bathrooms / sleeps 4

“We had a great vacation at this condo.” My family has been visiting indian rocks beach for nearly two decades, and we continue coming back to this resort and specifically, Martin's condo. It is always kept updated and we had a nice relaxing stay. It has WiFi for the kids and has a picture perfect view of the beach, ocean, sunsets and pool deck. You won't be disappointed.

Responds fast! avg. 2 hours 38 minutes

Price per night from

$228

EIKO BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK

Treasure Island house

4 bedrooms / 3 bathrooms / sleeps 13

“Location location location” Myself and six of my friends stayed here and had a great week! The location is perfect and the swimming pool was an added bonus due to the high winds.... we grilled and that was great, we never went into the hot tub but I’m sure that would have been great as well... The beach was amazing and the sitting area just as nice.... the game room was an added bonus and the group really enjoyed that.. We would definitely come back!! Liz, thanks for all the instructions and helpful hints!!!!!

Price per night from

$571

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