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Vacation Homes in Oldsmar

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
Enjoy al fresco dining with a round table and six chairs, overlooking the city and a body of water.

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!

10.0 out of 10, Exceptional, (69)
"We had so much fun at this beautiful home and wish we were still there!"
Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**
Enjoy cooking in this kitchen with a central island and bar stools, featuring appliances and a convenient coffee station.

*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**

9.8 out of 10, Exceptional, (68)
"The house is beautiful and the location was perfect for what we needed. "
*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
Guests can enjoy a serene beach experience with access to the shore.

Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass

9.6 out of 10, Exceptional, (235)
"great spot on the beach, walk to John's pass and other restraunts!"
$412 nightly
The price is $459
Aug 14 - Aug 15
Total includes taxes and fees
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
Breezy ‘White Sands House’ Steps to Gulf Shore!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances and a spacious tiled backsplash.

Breezy ‘White Sands House’ Steps to Gulf Shore!

9.6 out of 10, Exceptional, (103)
"Great access to the beach, parking on the property, and plenty of space to relax and hang out. "
Breezy ‘White Sands House’ Steps to Gulf Shore!
Centrally Located 3-Bedroom Oasis: 20 Mins to Beach and City Life on VRBO
Relax in this inviting living space with a large L-shaped sofa, coffee table, and patterned rug.

Centrally Located 3-Bedroom Oasis: 20 Mins to Beach and City Life on VRBO

7.0 out of 10, Good, (6)
"A beautiful house, very comfortable, it has a beautiful yard and the house is close to all the shops. "
Centrally Located 3-Bedroom Oasis: 20 Mins to Beach and City Life on VRBO
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
Relax in comfort on the beach with Adirondack chairs and enjoy a safe and well-maintained environment.

1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa

10.0 out of 10, Exceptional, (271)
"This property is amazing, and we would absolutely stay here again!"
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
Spacious home near Busch Gardens & USF w King Bed
Relax in this stylish living room with two sofas, a potted plant, and abstract art pieces.

Spacious home near Busch Gardens & USF w King Bed

8.2 out of 10, Very Good, (14)
"House was nice and cozy"
Spacious home near Busch Gardens & USF w King Bed
Mod 4BR Home, Heated Private Pool • Near Indian Shores & John’s Pass • Sleeps 10
Guests can enjoy the serene beach scene with calm waters and a lifeguard tower nearby.

Mod 4BR Home, Heated Private Pool • Near Indian Shores & John’s Pass • Sleeps 10

9.8 out of 10, Exceptional, (22)
"This property was fantastic. Plenty of room and amenities for all. Kitchen had everything we needed to make some easy meals. Pool was clean and warm. The whole property was well maintained. Would definitely book here again. "
Mod 4BR Home, Heated Private Pool • Near Indian Shores & John’s Pass • Sleeps 10
La Casita Blanca Ybor City Tampa
Cozy retreat with a white door, small window, and kitchenette area.

La Casita Blanca Ybor City Tampa

9.8 out of 10, Exceptional, (106)
"We are definitely planning to stay here again"
$136 nightly
The price is $152
Aug 11 - Aug 12
Total includes taxes and fees
La Casita Blanca Ybor City Tampa
Vacation Home 2 Miles From The Beach with Pool and Spillover Spa!
Relax in this stylish living room with a sofa set, coffee table, and large mirror.

Vacation Home 2 Miles From The Beach with Pool and Spillover Spa!

9.6 out of 10, Exceptional, (73)
"My family of 4 had a great stay here! The pool and outdoor living space was just awesome!! It was a great location and nice neighborhood! If we are in the area again, we’d definitely go back!"
Vacation Home 2 Miles From The Beach with Pool and Spillover Spa!
Heated Pool House <5 Min to Beaches Sleeps 12
Enjoy ocean views from the hotel's multi-story structure, set amidst a vibrant beachfront community with recreational opportunities.

Heated Pool House <5 Min to Beaches Sleeps 12

10.0 out of 10, Exceptional, (10)
"This house has a great location. It’s close to everything without being in the busy strip. Plus the lanai with the pool is an added plus!"
Heated Pool House <5 Min to Beaches Sleeps 12
Heated Pool | 2BD 2BA | Home near Beaches
Enjoy cooking in this well-equipped kitchen with appliances, granite countertop, and sink.

Heated Pool | 2BD 2BA | Home near Beaches

9.8 out of 10, Exceptional, (24)
"We enjoyed our stay! The location was great—close to the beach yet perfect for exploring Clearwater beyond the shore. The updated home is well-suited for families, friends, or any group, and the pool is a fantastic bonus."
Heated Pool | 2BD 2BA | Home near Beaches
Coastal Breeze - 90 seconds from door to sand. Heated pool with slide & spa.
Relax in this spacious living area with a large sofa, dining table, and fireplace.

Coastal Breeze - 90 seconds from door to sand. Heated pool with slide & spa.

10.0 out of 10, Exceptional, (44)
"Great place and great host!!"
Coastal Breeze - 90 seconds from door to sand. Heated pool with slide & spa.
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Enjoy the tranquil atmosphere of Clearwater Beach, where guests can soak up the sun and take in the breathtaking ocean views.

*Pool* 8.5 miles to Honeymoon Island. 4 bdr

10.0 out of 10, Exceptional, (42)
"Loved the area and comfortable accommodations. "
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Private Pinellas County Beaches' getaway house
Enjoy outdoor dining or relaxation in this serene patio area with a table and chairs, surrounded by a lush garden and a string of twinkling lights.

Private Pinellas County Beaches' getaway house

8.4 out of 10, Very Good, (42)
"Cindy was such a gracious host. She’s bubbly and warm, made us feel right at home! Came for a weekend beach trip and this was perfect as it was only 15-20 min from the beach and there’s many restaurants and grocery stores nearby, so the location was perfect. We highly recommend staying here; great experience overall. "
$141 nightly
The price is $157
Aug 10 - Aug 11
Total includes taxes and fees
Private Pinellas County Beaches' getaway house
Charming Clean Studio in Downtown Clearwater
Simple, single-story building with a blue door and a chair outside, surrounded by palm trees and a gravel pathway.

Charming Clean Studio in Downtown Clearwater

9.6 out of 10, Exceptional, (14)
"Everything was as advertised. Great location for beach in clearwater and tampa."
$123 nightly
The price is $136
Aug 10 - Aug 11
Total includes taxes and fees
Charming Clean Studio in Downtown Clearwater
Spacious Tampa Haven: Games / Pool / 7-15 min From Everything
Relax in this stylish living room with a sofa, flat-screen TV, and vibrant artwork.

Spacious Tampa Haven: Games / Pool / 7-15 min From Everything

9.2 out of 10, Wonderful, (12)
"Beautiful home, the Owner was very friendly and accommodating to our needs. Responded to emails in a timely manner. Next time I'm in Tampa I would love to stay here again."
Spacious Tampa Haven: Games / Pool / 7-15 min From Everything
House with unique style 3/2 Near Raymond Stadium
Enjoy cooking in this well-equipped kitchen with oven, microwave, and coffee maker.

House with unique style 3/2 Near Raymond Stadium

7.6 out of 10, Good, (63)
"Perfect for what we needed to attend NY Yankees spring training games. "
$217 nightly
The price is $244
Aug 11 - Aug 12
Total includes taxes and fees
House with unique style 3/2 Near Raymond Stadium
5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub
Relax by the serene pool surrounded by lush greenery and trees.

5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub

9.2 out of 10, Wonderful, (47)
"We wanted to check out south Tampa and we’re happy with this location for our two week stay. Kids loved the pool and hot tub everyday! "
$334 nightly
The price is $375
Sep 2 - Sep 3
Total includes taxes and fees
5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub
Clearwater Beach House - Right On The Beach
Enjoy a serene beach experience with calm seas and gentle waves.

Clearwater Beach House - Right On The Beach

9.6 out of 10, Exceptional, (111)
"Convenient to Beach and local restaurants"
$452 nightly
The price is $504
Aug 12 - Aug 13
Total includes taxes and fees
Clearwater Beach House - Right On The Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oldsmar Hotel Reviews

Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

10/10 Excellent
"Accessible to variety of everything in the area. Negative point was the male cook employee monitoring who was coming for breakfast. Didn't know he was also security 😳 "
Esteban 5-night trip
Posted 22 hours ago
Pier House 60 Clearwater Beach Marina Hotel