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2,670 Houses

(2) Very Good 

11

Luxury ground floor Condo for rent

Florida / Oldsmar

Oldsmar condo

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$77

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$77

29

BAY VIEW PARADISE!!

Florida / Oldsmar

Oldsmar house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$115

Price per night from

$115

16

Villa for renting in Oldsmar FL available on December 1st, contract for one year

Florida / Oldsmar

Oldsmar villa

2 4 90 nights min

  • 2 bedrooms
  • sleeps 4
  • 90 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

19

Your perfect family vacation! Just a few steps away from the Tampa Bay's waters

Florida / Oldsmar

Oldsmar house

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$170

Price per night from

$170

Great rentals within 20 miles that match your search

Distance approx 15.41 km from Oldsmar

5

King pillow top with waffles and wifi

Florida / Tampa

Tampa house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Air conditioning

Price per night from

$52

Responds fast!
avg. 1 hour 13 minutes

Price per night from

$52

Distance approx 15.81 km from Oldsmar

(1) Excellent 

19

gulfside 316

Florida / Indian Rocks Beach

Indian Rocks Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$166

Price per night from

$166

Distance approx 16.81 km from Oldsmar

(2) Excellent 

24

Indian Shores Beach Cottage

Florida / Indian Shores

Indian Shores cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$201

Price per night from

$201

Distance approx 15.72 km from Oldsmar

20

Paradise Lakes (Clothing Optional): Garden of Eden

Florida / Tampa

Tampa apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 48 mi
  • Swimming pool

Price per night from

$138

Price per night from

$138

Distance approx 14.87 km from Oldsmar

29

Updated Gorgeous Gulf Front Condo with big Balcony

Florida / Indian Rocks Beach

Indian Rocks Beach apartment

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$299

Price per night from

$299

Distance approx 16.01 km from Oldsmar

(5) Very Good 

21

Indian Rocks Beach

Florida / Indian Rocks Beach

Indian Rocks Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Florida 2017 vacation” We stayed in room 107 at 50 Gulfside condo. It was a quite relaxing condition with everything we needed. I always appreciate comfortable beds and thick towels. We had that. There was a few nice restaurants walking distance a
…see more

Price per night from

$164

Price per night from

$164

Distance approx 18.41 km from Oldsmar

(15) Excellent 

21

Beautiful Beachfront Condo on the FL Gulf Coast

Florida / Madeira Beach

Madeira Beach apartment

2 6 14 nights min

  • 2 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary
“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
…see more

Price per night from

$184

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$184

Distance approx 18.15 km from Oldsmar

(1) Excellent 

28

#1 Gulf Coast Property on TripAdvisor!

Florida / Madeira Beach

Madeira Beach condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$138

Price per night from

$138

Distance approx 9.63 km from Oldsmar

(15) Excellent 

Certificate of Excellence

31

Beautiful 2 bedroom condo,mins. drive to beach, pool

Clearwater / Clearwater Beach

Clearwater apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$115

Responds fast!
avg. 9 minutes

Price per night from

$115

Distance approx 16.98 km from Oldsmar

(10) Very Good 

16

Barefoot Beach Resort! On WATER-Steps to Beach!

Florida / Indian Shores

Indian Shores condo

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“New Year’s getaway” What a lovely time in our clean comfortable condo! The entire time was just wonderful! From check in to check out everything was perfect! Everyone was very friendly and made you feel at home! I love staying here because of the
…see more

Price per night from

$126

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$126

Distance approx 9.65 km from Oldsmar

(27) Excellent 

Certificate of Excellence

46

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

Florida / Clearwater

Clearwater condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$132

Responds fast!
avg. 15 minutes

Price per night from

$132

Distance approx 16.69 km from Oldsmar

(2) Excellent 

45

Boca Ciega Resort & Marina - Waterfront View! Watch Dolphins from Balcony!

Florida / St. Petersburg

St. Petersburg condo

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$112

Responds fast!
avg. 1 hour 0 minutes

Price per night from

$112

Distance approx 14.79 km from Oldsmar

(1) Excellent 

29

Best IRB Location - Close to Restaurants and Shops

Florida / Indian Rocks Beach

Indian Rocks Beach apartment

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$184

Responds fast!
avg. 1 hour 4 minutes

Price per night from

$184

Distance approx 15.72 km from Oldsmar

(54) Excellent 

37

Gulffront Cottages Sandy Shores/PATIO

Florida / Indian Rocks Beach

Indian Rocks Beach cottage

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Family vacation” Wonderful place gorgeous views comfortable and relaxing you couldn't ask for more in a vacation spot great location.
…see more

Price per night from

$143

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$143

Distance approx 10.6 km from Oldsmar

31

Villas of Clearwater Beach - A17

Florida / Clearwater

Clearwater condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$237

Responds fast!
avg. 45 minutes

Price per night from

$237

Distance approx 10.74 km from Oldsmar

19

Perfect Location, Walk to Everything, All Suites Condo Motel, Full Kitchen

Florida / Clearwater

Clearwater hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Car not necessary

Price per night from

$160

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$160

Distance approx 16.54 km from Oldsmar

21

Best View in Indian Shores, Enjoy some Paradise, Heated pool, Fishing dock, WiFi

Florida / Indian Shores

Indian Shores condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$130

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$130

Distance approx 17.61 km from Oldsmar

(1) Excellent 

17

B & B's Winter Getaway

Florida / St. Petersburg

St. Petersburg house

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$321

Price per night from

$321

Distance approx 19.47 km from Oldsmar

(13) Very Good 

21

South Beach Gulf Front Luxury Condo

Florida / Treasure Island

Treasure Island apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Very bad Bed” This a really nice place. The staff are real nice. I would like to rent it again. But the is so bad you may want to sleep on the floor.
…see more

Price per night from

$136

Price per night from

$136

Distance approx 13.48 km from Oldsmar

43

NEW: Soar the Heights, Southeast Seminole Heights!

Florida / Tampa

Tampa guest house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$69

Price per night from

$69

Distance approx 9.65 km from Oldsmar

30

Clearwater Avalon Palm 2 Bed. Vacation Condo

Florida / Clearwater

Clearwater condo

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$108

Responds fast!
avg. 40 minutes

Price per night from

$108

Distance approx 11.26 km from Oldsmar

26

Luxurious Vacation Home in Tampa

Florida / Tampa

Tampa house

5 12 1 night min

  • 5 bedrooms
  • sleeps 12
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$667

Price per night from

$667

Distance approx 10.97 km from Oldsmar

15

July 4th Getaway

Florida / Clearwater

Clearwater condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$344

Price per night from

$344

Distance approx 8.53 km from Oldsmar

13

Spend a great holiday in Florida

Florida / Clearwater

Clearwater house

2 2 30 nights min

  • 2 bedrooms
  • sleeps 2
  • 30 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$57

Price per night from

$57

Distance approx 10.52 km from Oldsmar

(5) Excellent 

25

Seaside Cottages

Florida / Clearwater

Clearwater apartment

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Nearest beach 0 mi
  • Car not necessary
  • Air conditioning
“Perfect Location in North Beach!” My husband and I stayed at Seaside Cottages for the month of April. The cottages are connected to the back of the main house with a small shared patio. We had access to the washer and dryer, beach chairs, and a park
…see more

Price per night from

$77

Price per night from

$77

Distance approx 16.93 km from Oldsmar

16

Indian Shores spacious 2 bdrm new furnishings Intra coastal View

Florida / Indian Shores

Indian Shores apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly

Price per night from

$131

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$131

Distance approx 17.58 km from Oldsmar

12

Vintage 2 Bed / 2 Bath With Pool- Blocks from Vinoy & Downtown St. Pete

Florida / St. Petersburg

St. Petersburg house

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Child Friendly

Price per night from

$115

Price per night from

$115

Distance approx 19.42 km from Oldsmar

25

"Beach-U-Tuit" on Treasure Island, FL

Florida / Treasure Island

Treasure Island condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0 mi

Price per night from

$192

Price per night from

$192

Distance approx 10.37 km from Oldsmar

29

Clearwater Home - 200 Steps from the Beach!

Florida / Clearwater

Clearwater house

3 12 min stay varies

  • 3 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$463

Responds fast!
avg. 9 minutes

Price per night from

$463

Distance approx 17.43 km from Oldsmar

(44) Very Good 

43

**PERFECT FOR A FAMILY VACATION** 3Br Directly On The Beach

Florida / Indian Shores

Indian Shores condo

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$152

Responds fast!
avg. 3 hours 14 minutes

Price per night from

$152

Distance approx 18.23 km from Oldsmar

(1) Excellent 

66

5 Star Beach House! Sleeps 14, Bikes, 2 Kitchens!

Florida / Redington Beach

Redington Beach house

5 14 3 nights min

  • 5 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$342

Price per night from

$342

Distance approx 11.53 km from Oldsmar

18

One Bedroom Cottage in Rainbow Village RV Resort in Vibrant Largo

Florida / Largo

Largo cottage

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$71

Price per night from

$71

Distance approx 10.26 km from Oldsmar

(9) Very Good 

35

Gardenia Beach Hideaway "Private pool & hot tub!"

Florida / Clearwater

Clearwater house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$217

Price per night from

$217

Distance approx 18.75 km from Oldsmar

17

309 - 2 bd. Luxury Condo with easy beach access and lagoon is behind building

Florida / Madeira Beach

Madeira Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$218

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$218