Oldsmar vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Oldsmar

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Tampa

4.78 out of 5 average rating, 221 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Papa’s Cozy, Rustic, Oceanfront Fishing Cabin. Brand new dock installed January 2024! 2 kayaks, 2 bikes, & fishing rods provided. Old Florida style neighborhood near charming Oldsmar on a Saltwater Gulf canal, only a few houses down from open bay. Great for the outdoorsy vacationer. The depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Proudly dog friendly! Not suited for everyone. If you’re looking for luxury this is not the place for you!

May 18 – 25

ﺩ.ﺇ614 per night
Guest favorite

Tiny home in Oldsmar

4.96 out of 5 average rating, 241 reviews

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants ,This Private1BD/1BA Cottage is split down the middle you have your own entrance And private space to yourself. Don’s place is on your left and Louisa’s cottage is on your right side.This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

Jul 25 – Aug 1

ﺩ.ﺇ391 per night
Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 193 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Jun 4 – 11

ﺩ.ﺇ383 per night

Popular amenities for Oldsmar vacation rentals

Stay near Oldsmar's top sights

Mease Countryside Hospital6 locals recommend
Philippe Park60 locals recommend
Oldsmar Flea Market33 locals recommend
Walmart Supercenter13 locals recommend
AMC Woodlands Square 2024 locals recommend
John Chesnut Senior Park35 locals recommend

Other great vacation rentals in Oldsmar

Guest favorite

Apartment in Tampa

4.92 out of 5 average rating, 115 reviews

Stunning Studio in Citrus Park

Jun 3 – 10

ﺩ.ﺇ348 per night
Guest favorite

Apartment in Safety Harbor

4.92 out of 5 average rating, 162 reviews

The Downtown Studio

Dec 10 – 17

ﺩ.ﺇ497 per night
Guest favorite

Home in Oldsmar

4.85 out of 5 average rating, 62 reviews

Private In-Law Suite with Beautiful Bay View

Nov 12 – 19

ﺩ.ﺇ414 per night
Guest favorite

Guest suite in Oldsmar

4.91 out of 5 average rating, 95 reviews

Quiet Bay Getaway-Hot Tub-Dog friendly-Bikes

Jun 17 – 24

ﺩ.ﺇ387 per night
Guest favorite

Home in Oldsmar

4.88 out of 5 average rating, 94 reviews

Coastal themed home near beach and airport

Nov 24 – Dec 1

ﺩ.ﺇ528 per night
Guest favorite

Apartment in Oldsmar

4.91 out of 5 average rating, 56 reviews

Modern 2nd Floor Two Bedroom Apt with Pool

May 27 – Jun 3

ﺩ.ﺇ531 per night
Guest favorite

Guesthouse in Clearwater

5.0 out of 5 average rating, 21 reviews

Cozy In-Law Suite Near Beach

Jun 26 – Jul 3

ﺩ.ﺇ309 per night
Guest favorite

Guesthouse in Oldsmar

4.98 out of 5 average rating, 47 reviews

salt living at its best

Dec 3 – 10

ﺩ.ﺇ697 per night
Guest favorite

Cottage in Dunedin

4.96 out of 5 average rating, 74 reviews

BeachBunkies Cottage 1. Four miles to the beach!

Sep 19 – 26

ﺩ.ﺇ352 per night
Guest favorite

Guesthouse in Tarpon Springs

5.0 out of 5 average rating, 25 reviews

Bayoutiful Getaway

Mar 7 – 14

ﺩ.ﺇ378 per night
Guest favorite

Farm stay in Odessa

4.98 out of 5 average rating, 46 reviews

The Cabins At Cahaba - Cabin 3

Dec 4 – 11

ﺩ.ﺇ335 per night
Guest favorite

Guest suite in Odessa

5.0 out of 5 average rating, 71 reviews

GREAT ESCAPE for the Road Warrior.

Sep 29 – Oct 6

ﺩ.ﺇ379 per night

Other great vacation rentals in Oldsmar

Guest favorite

Guesthouse in Tampa

5.0 out of 5 average rating, 44 reviews

Peaceful Cottage and Koi Pond Gardens

Nov 20 – 27

ﺩ.ﺇ618 per night
Guest favorite

Cottage in Safety Harbor

5.0 out of 5 average rating, 21 reviews

"Sweet Harbor Cottage" Walk to Downtown

Jul 2 – 9

ﺩ.ﺇ510 per night
Guest favorite

Condo in Palm Harbor

4.97 out of 5 average rating, 31 reviews

Beautiful 1 bedroom Condo / Innisbrook Golf Resort

Jul 20 – 27

ﺩ.ﺇ529 per night
Superhost

Home in Tampa

4.92 out of 5 average rating, 77 reviews

Guest House on private lake in Westchase

Sep 2 – 9

ﺩ.ﺇ448 per night
Guest favorite

Apartment in Palm Harbor

4.95 out of 5 average rating, 19 reviews

Surfs up! apartment in historic downtown

Jun 9 – 16

ﺩ.ﺇ380 per night
Guest favorite

Home in Holiday

4.85 out of 5 average rating, 41 reviews

Comfortable house near Tarpon Springs & Beaches

Nov 23 – 30

ﺩ.ﺇ448 per night
Superhost

Guesthouse in Dunedin

4.83 out of 5 average rating, 52 reviews

Guest House in prime location!

Jun 11 – 18

ﺩ.ﺇ325 per night
Guest favorite

Home in Oldsmar

4.99 out of 5 average rating, 67 reviews

Fountain House On Timberbay Lake

Nov 13 – 20

ﺩ.ﺇ810 per night
Guest favorite

Apartment in Palm Harbor

5.0 out of 5 average rating, 6 reviews

Innisbrook Golf Resort Condo

May 9 – 16

ﺩ.ﺇ422 per night
Guest favorite

Home in Palm Harbor

4.97 out of 5 average rating, 38 reviews

Hatties Hill Florida

Aug 19 – 26

ﺩ.ﺇ391 per night
Guest favorite

Guest suite in Safety Harbor

5.0 out of 5 average rating, 48 reviews

Welcome to beautiful and peaceful Blue Heaven.

Dec 11 – 18

ﺩ.ﺇ565 per night
Guest favorite

Home in Oldsmar

4.85 out of 5 average rating, 48 reviews

Modern & Spacious Retreat with Private Pool!

Nov 25 – Dec 2

ﺩ.ﺇ792 per night

Quick stats about vacation rentals in Oldsmar

Total rentals

130 properties

Rentals with a pool

60 properties have a pool

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

3.6K reviews

Nightly prices starting at

ﺩ.ﺇ73 before taxes and fees

Frequently Asked Questions

  • Where should I stay in Oldsmar?

    Make yourself at home in Oldsmar by choosing from our most frequently booked neighborhoods. We have over 540 vacation rentals in The Grove Of Laforest, over 190 vacation rentals in East Lake Woodlands, and over 190 vacation rentals in Bridlewood.

  • Are there pet-friendly vacation rentals in Oldsmar?

    Four-legged friends are welcome in Oldsmar. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oldsmar?

    Yes! Work meets play with ease at over 70 vacation rentals in Oldsmar featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Oldsmar vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Oldsmar have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oldsmar have air conditioning?

    Absolutely! We offer over 80 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oldsmar have wireless internet?

    Absolutely! We offer over 80 house rentals with wireless internet in Oldsmar. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Oldsmar?

    Experience the best of Oldsmar with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Oldsmar?

    Oldsmar has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Oldsmar?

    Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with air conditioning, over 30 homes with a bbq area, over 80 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Oldsmar