Updating...

More filters (1)

Swimming pool
Wireless Internet
Air conditioning
Private pool

Heated pool
Private indoor pool
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Fax machine
Pool or snooker table
Table tennis
Games room
Shared outdoor pool (heated)
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Video player
Climbing frame
Boat available
Fridge
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Staffed property
Microwave
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

See all

Less

Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

See all

Less

Skiing – property near ski resort
Walking trips
Tennis in town
Nightlife

Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Golf within 30mins drive
Lakefront
Waterfront

See all

Less

887 Houses in Oldsmar with pools

Sort by:

Dolphin Bay Retreat

Oldsmar house

2 bedrooms
1 bathroom

sleeps 8

Match: Swimming pool

All filters match

Price per night from

$287

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

5 bedrooms
3 bathrooms

sleeps 8

Match: Swimming pool

All filters match

Price per night from

$286

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

Oldsmar apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$327

La Rustic House

Oldsmar house

3 bedrooms
2 bathrooms

sleeps 9

Match: Swimming pool

All filters match

Price per night from

$389

Great rentals within 20 miles that match your search

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

1 bedroom
1 bathroom

sleeps 2

Match: Swimming pool

All filters match

Price per night from

$172

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

1 bedroom
1 bathroom

sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

Match: Swimming pool

All filters match

Price per night from

$161

Summer special!

Madeira Beach condo

2 bedrooms
1 bathroom

sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

Match: Swimming pool

All filters match

Price per night from

$114

Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$344

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

2 bedrooms
2 bathrooms

sleeps 5

Match: Swimming pool

All filters match

Price per night from

$218

Relaxation at the Tropical Pool House

Tampa house

4 bedrooms
2 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$446

Take a step closer to paradise! SEAGATE – Apt. 302

Indian Shores apartment

3 bedrooms
2 bathrooms

sleeps 6

“Would love to return several times a year....near perfect!” The condo was beautiful, well appointed and maintained. Located on a nearly perfect beach. It appears we were the first tenants after hurricane Irma. My only complaint was the AC didn't work for the 1st half. The property manager seemed to be doing all she could to remedy the situation My only recommendation is that maintenance should probably have checked it out along with everything else after the storm. I would still highly recommend this to anyone wanting to experience a beach vacation in a great location and in a wonderful condo. The owner is great to work with also.

Match: Swimming pool

All filters match

Price per night from

$344

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

1 bedroom
2 bathrooms

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$84

SUNSHINE HOLIDAY

St. Petersburg manor house

5 bedrooms
6 bathrooms

sleeps 10

Match: Swimming pool

All filters match

Price per night from

$1,145

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$1,052

Seminole Vacation House Spacious Vacation House

Seminole house

3 bedrooms
2 bathrooms

sleeps 7

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$107

1BR Pool View Condo in Clearwater Florida

Clearwater condo

1 bedroom
1 bathroom

sleeps 4

“Outstanding as usual.” Second year staying at the Avalon. Great location! About 5 miles to the beach one way, and about 6.5 the other way. Everything needed is within walking distance. Pool is great if the beach isn't your thing. Excellent workout room.

Match: Swimming pool

All filters match

Price per night from

$103

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

1 bedroom
1 bathroom

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$287

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$368

Luxury waterfront Condo Rooftop Terrace

Clearwater house

3 bedrooms
3 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$567

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

3 bedrooms
2 bathrooms

sleeps 8

Match: Swimming pool

All filters match

Price per night from

$516

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

1 bedroom
1 bathroom

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$92

440 West Condos 508-S Gulf Front Condo

Clearwater apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$480

Surfside Condos 303 Beachfront Condo

Clearwater apartment

2 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$1,227

Mandalay Beach Club 603-P Beachfront Condo - One Month Minimum

Clearwater apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$321

Regatta Beach Club C1009 '90 day min stay with 2 week lead time'

Clearwater apartment

2 bedrooms
1 bathroom

sleeps 8

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$118

Intercoastal 209 Water View from this Charming Condo

Indian Shores apartment

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$5,190

440 West Condos 1408-N Gulf Front Condo with amazing views

Clearwater apartment

1 bedroom
2 bathrooms

sleeps 2

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$179

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$1,417

Harborview Grande 802 Luxury Waterfront Penthouse

Clearwater apartment

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$250

Bay Harbor 302 Radiant Water View of the Bay

Clearwater apartment

3 bedrooms
3 bathrooms

sleeps 8

“Great location, great condo, great price!” My family loved staying at bay harbor 302! The location was perfect, only a short 3-4 min walk to the pristine beaches. The condo was impeccable and much bigger than the pictures suggest. I cooked a lot of meals there and never did I lack anything I needed. The cooking skillets could have used an upgrade but they did the job. The bathrooms and kitchen were very up to date and clean. The bedrooms were a great size. The view from the balcony was wonderful and there was always a breeze when enjoying morning coffee or after dinner drinks. There were so many amazing restaurants within walking distance as well as great "touristy" shops. The reserved parking was great and we felt secure with having a gate at the entrance which required a code, The lobby door requiring a code, and a code for our condo door. Clearwater Beach Rentals were very accommodating and when we asked if we could check in a few hours early they made it happen. Everyone was very kind and we definitely plan on booking through them again. All in all our stay was wonderful!

Responds fast! avg. 2 hours 30 minutes

Match: Swimming pool

All filters match

Price per night from

$232