Our other sites
Get A Free World Heritage Guide »
SeatGuru
Family Vacation Critic
Cruise Critic
BookingBuddy
We recommend:
We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Oldsmar Vacation Rentals

Hotels (4)

B&Bs / Inns (0)

Specialty Lodging (0)

Vacation Rentals (697)

The safest rental experience online

Rent from verified owners and managers, and read reviews before you book.

Find out what to expect »

In partnership with:

Get listed!

Add your property »

Featured listings
Isla Del Sol - Bahia Del Mar P-406, St. Petersburg
Isla Del Sol - Bahia Del Mar P-406
    Price: €1,569/month
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
  • Min stay: 30
    • Contact Manager
Special December Rates @ Prestigious Ocean Sands, Madeira Beach
Special December Rates @ Prestigious Ocean Sands
    Price: €65 - €100/night €453 - €697/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
  • Min stay: 14
    • Contact Owner
Lands End 4-402, Treasure Island
Lands End 4-402
    Price: €540 - €906/week €2,315 - €3,311/month
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
    • Contact Manager
A perfect place for a couple, Mango Tango Cottage, Clearwater
A perfect place for a couple, Mango Tango Cottage
    Price: €415/week
  • Bedrooms: 1, sleeps 2
  • Bathrooms: 1
    • Contact Owner
Parsley's Paradise - Pool & Belleair Beach Views!, Belleair Beach
Parsley's Paradise - Pool & Belleair Beach Views!
    Price: €1,185 - €1,429/week €3,555 - €4,287/month
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 3
  • Min stay: 7
    • Contact Owner
Isla Del Sol, Palma Del Mar Condo, St. Petersburg
Isla Del Sol, Palma Del Mar Condo
    Price: €1,255 - €1,743/month
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
  • Min stay: 30
    • Contact Owner
Tropic Breezes 19, Madeira Beach
Tropic Breezes 19
    Price: €338 - €519/week €1,143 - €1,737/month
  • Bedrooms: 1, sleeps 4
  • Bathrooms: 1
    • Contact Manager
Tropic Breezes 20, Madeira Beach
Tropic Breezes 20
    Price: €338 - €519/week €1,143 - €1,737/month
  • Bedrooms: 1, sleeps 5
  • Bathrooms: 1
    • Contact Manager
Tropic Breezes 13, Madeira Beach
Tropic Breezes 13
    Price: €338 - €519/week €1,143 - €1,737/month
  • Bedrooms: 1, sleeps 4
  • Bathrooms: 1
    • Contact Manager
Tropic Breezes 10, Madeira Beach
Tropic Breezes 10
    Price: €338 - €519/week €1,143 - €1,737/month
  • Bedrooms: 1, sleeps 2
  • Bathrooms: 1
    • Contact Manager

Search Oldsmar Vacation Rentals

Clear dates

Advanced Search

Recommended by Travelers

[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]

There are no vacation rentals within Oldsmar, Florida. We broadened your search to include all rentals within 25 miles.

Beach Dreams - Indian Shores Florida, Indian Shores
Beach Dreams - Indian Shores Florida
Contact Owner
4.5 of 5 stars 10 reviews
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Min stay:7
Our beautiful Beach Cottage II unit sits conveniently on the first floor with a direct walkout to the large pool deck, jacuzzi, bbq and BEACH! Indian Shores ...
  • Nightly
    --
  • Weekly
    €540 - €959
  • Monthly
    --
Sea Rocket 7, North Redington Beach
Sea Rocket 7
Contact Manager
Nightly rate from
€52
4.5 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Sleeps: 4
Bathrooms: 1
All New in September 2009! Groud floor, Gulf Front corner condo.2 night rental minimum/3 night minimum over holidays Check-In: 3:00 pm Check-Out: 10:00 am
  • Nightly
    €52 - €66
  • Weekly
    €348 - €441
  • Monthly
    €1,342 - €1,700
Emerald Dunes #301, Crystal Beach
Emerald Dunes #301
Contact Manager
Nightly rate from
€95
4.5 of 5 stars 9 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
This two bedroom beachfront vacation accommodation is perfect for your next retreat to the beach. Decorated in pleasing neutrals you will feel a sense of calm ...
  • Nightly
    €95 - €266
  • Weekly
    €591 - €1,530
  • Monthly
    --
#225 Surf Song Condo, Madeira Beach
#225 Surf Song Condo
Contact Manager
Nightly rate from
€63
4.5 of 5 stars 7 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath poolside - No balcony NON SMOKINGQueen in master bedroom, twins in second & sofabed in livingroom.Recent upgrades: New kitchen, appliances ...
  • Nightly
    €63 - €105
  • Weekly
    €383 - €652
  • Monthly
    --
Lands End 5-305, Treasure Island
Lands End 5-305
Contact Manager
4.5 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
At the very southern tip of Treasure Island, this 3rd floor, corner unit has an expansive view of the Gulf of Mexico from the balcony, living and dining ...
  • Nightly
    --
  • Weekly
    €575 - €976
  • Monthly
    €2,218 - €3,364
Crystal Escape, Crystal Beach
Crystal Escape
Contact Manager
Nightly rate from
€167
4.5 of 5 stars 12 reviews
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 18
Bathrooms: 4
Escape to the beach, to the charming Crystal Beach community in Destin, Florida. Private pool , screened-in porch and a short walk to the beach await you ...
  • Nightly
    €167 - €439
  • Weekly
    €1,034 - €2,527
  • Monthly
    --
Harbor View Grande, Clearwater
Harbor View Grande
Contact Owner
4.5 of 5 stars 5 reviews
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Here’s the real deal for a truly wonderful vacation rental! Rich wood cabinets and beautiful granite in the kitchen. Cool tile throughout except for ...
  • Nightly
    --
  • Weekly
    €1,112
  • Monthly
    --
#305 Crimson Condo, Madeira Beach
#305 Crimson Condo
Contact Manager
Nightly rate from
€73
4.5 of 5 stars 10 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath beach view balcony -non front 1225 sq ftKing in master, queen & single in second. 3 t.v.'sWasher/Dryer NON SMOKING - Free High speed ...
  • Nightly
    €73 - €129
  • Weekly
    €485 - €837
  • Monthly
    --
Sea Gate 504, Indian Shores
Sea Gate 504
Contact Manager
4 of 5 stars 3 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Spectacular views from the huge balcony of this top floor Sea Gate condo! Rental includes unlimited North American long distance and High Speed Internet ...
  • Nightly
    --
  • Weekly
    €680 - €1,115
  • Monthly
    €2,622 - €3,855
#114 Surf Song Condo, Madeira Beach
#114 Surf Song Condo
Contact Manager
Nightly rate from
€63
4 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath near pool-Non beach View - No balcony NON SMOKINGKing in master , twins in 2nd, Ground Floor, NO SLEEPER SOFANicely decorated, recently ...
  • Nightly
    €63 - €105
  • Weekly
    €383 - €652
  • Monthly
    --
#121 Surf Song Condo, Madeira Beach
#121 Surf Song Condo
Contact Manager
Nightly rate from
€66
4 of 5 stars 5 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath beach front - No balcony NON SMOKINGKing in master bedroom, twins in second and no sofa bed.Nicely furnished, w/ picture window overlooking ...
  • Nightly
    €66 - €112
  • Weekly
    €415 - €687
  • Monthly
    --
#228 Surf Song Condo, Madeira Beach
#228 Surf Song Condo
Contact Manager
Nightly rate from
€56
4 of 5 stars 4 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath near pool - No balcony NON SMOKINGQueen bed in master, twins in second & sofabed in living room.2nd floor unit with all the comforts of ...
  • Nightly
    €56 - €105
  • Weekly
    €345 - €652
  • Monthly
    --
#224 Surf Song Condo, Madeira Beach
#224 Surf Song Condo
Contact Manager
Nightly rate from
€63
4 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath poolside - No balcony NON SMOKINGKing in Master, 2 Singles in second & sofabed.All new inside. New kitchen, appliances and furniture. Flat ...
  • Nightly
    €63 - €105
  • Weekly
    €383 - €652
  • Monthly
    --
#203 Crimson Condo, Madeira Beach
#203 Crimson Condo
Contact Manager
Nightly rate from
€101
4.5 of 5 stars 9 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 3
3 bedroom 3 bath beach view (side) balcony 1570 sq ftKing, King, twins, NON-SMOKING MAX 6 GUESTSWasher/Dryer - Free Highspeed Internet Policy: Non ...
  • Nightly
    €101 - €143
  • Weekly
    €638 - €903
  • Monthly
    --
#501 Beach Place, Madeira Beach
#501 Beach Place
Contact Manager
Nightly rate from
€59
4 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
2 bedroom 2 bath Pass View balcony 1300 sq ft- ADULTS ONLY1 qn in master, 2 dbl in 2nd BR - NO SLEEPER-NO SMOKING 1 Parking space-No Visitor Parking, COIN ...
  • Nightly
    €59 - €112
  • Weekly
    €415 - €694
  • Monthly
    --
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns