Oldsmar vacation rentals
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Top-rated vacation rentals in Oldsmar
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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
Tiny home in Oldsmar
4.96 out of 5 average rating, 241 reviewsLouisa'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
Guesthouse in Palm Harbor
4.97 out of 5 average rating, 193 reviewsPrivate 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar
Apartment in Tampa
4.92 out of 5 average rating, 115 reviewsStunning Studio in Citrus Park
Jun 3 – 10
Apartment in Safety Harbor
4.92 out of 5 average rating, 162 reviewsThe Downtown Studio
Dec 10 – 17
Home in Oldsmar
4.85 out of 5 average rating, 62 reviewsPrivate In-Law Suite with Beautiful Bay View
Nov 12 – 19
Guest suite in Oldsmar
4.91 out of 5 average rating, 95 reviewsQuiet Bay Getaway-Hot Tub-Dog friendly-Bikes
Jun 17 – 24
Home in Oldsmar
4.88 out of 5 average rating, 94 reviewsCoastal themed home near beach and airport
Nov 24 – Dec 1
Apartment in Oldsmar
4.91 out of 5 average rating, 56 reviewsModern 2nd Floor Two Bedroom Apt with Pool
May 27 – Jun 3
Guesthouse in Clearwater
5.0 out of 5 average rating, 21 reviewsCozy In-Law Suite Near Beach
Jun 26 – Jul 3
Guesthouse in Oldsmar
4.98 out of 5 average rating, 47 reviewssalt living at its best
Dec 3 – 10
Cottage in Dunedin
4.96 out of 5 average rating, 74 reviewsBeachBunkies Cottage 1. Four miles to the beach!
Sep 19 – 26
Guesthouse in Tarpon Springs
5.0 out of 5 average rating, 25 reviewsBayoutiful Getaway
Mar 7 – 14
Farm stay in Odessa
4.98 out of 5 average rating, 46 reviewsThe Cabins At Cahaba - Cabin 3
Dec 4 – 11
Guest suite in Odessa
5.0 out of 5 average rating, 71 reviewsGREAT ESCAPE for the Road Warrior.
Sep 29 – Oct 6
Other great vacation rentals in Oldsmar
Guesthouse in Tampa
5.0 out of 5 average rating, 44 reviewsPeaceful Cottage and Koi Pond Gardens
Nov 20 – 27
Cottage in Safety Harbor
5.0 out of 5 average rating, 21 reviews"Sweet Harbor Cottage" Walk to Downtown
Jul 2 – 9
Condo in Palm Harbor
4.97 out of 5 average rating, 31 reviewsBeautiful 1 bedroom Condo / Innisbrook Golf Resort
Jul 20 – 27
Home in Tampa
4.92 out of 5 average rating, 77 reviewsGuest House on private lake in Westchase
Sep 2 – 9
Apartment in Palm Harbor
4.95 out of 5 average rating, 19 reviewsSurfs up! apartment in historic downtown
Jun 9 – 16
Home in Holiday
4.85 out of 5 average rating, 41 reviewsComfortable house near Tarpon Springs & Beaches
Nov 23 – 30
Guesthouse in Dunedin
4.83 out of 5 average rating, 52 reviewsGuest House in prime location!
Jun 11 – 18
Home in Oldsmar
4.99 out of 5 average rating, 67 reviewsFountain House On Timberbay Lake
Nov 13 – 20
Apartment in Palm Harbor
5.0 out of 5 average rating, 6 reviewsInnisbrook Golf Resort Condo
May 9 – 16
Home in Palm Harbor
4.97 out of 5 average rating, 38 reviewsHatties Hill Florida
Aug 19 – 26
Guest suite in Safety Harbor
5.0 out of 5 average rating, 48 reviewsWelcome to beautiful and peaceful Blue Heaven.
Dec 11 – 18
Home in Oldsmar
4.85 out of 5 average rating, 48 reviewsModern & Spacious Retreat with Private Pool!
Nov 25 – Dec 2
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.
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