Holiday rentals in Oldsmar

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Top-rated holiday rentals in Oldsmar

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

Guest favourite

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!

17–24 May

€ 185 per night
Guest favourite

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.

29 Aug – 5 Sep

€ 109 per night
Guest favourite

Guest house 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.

4–11 Jun

€ 114 per night

Popular amenities for Oldsmar holiday 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 holiday rentals in Oldsmar

Guest favourite

Guest house in Oldsmar

4.98 out of 5 average rating, 47 reviews

salt living at its best

22–29 Aug

€ 207 per night
Guest favourite

Cottage in Dunedin

4.96 out of 5 average rating, 74 reviews

BeachBunkies Cottage 1. Four miles to the beach!

19–26 Sep

€ 114 per night
Guest favourite

Guest suite in Odessa

5.0 out of 5 average rating, 71 reviews

GREAT ESCAPE for the Road Warrior.

17–24 May

€ 109 per night
Guest favourite

Guest house in Tarpon Springs

5.0 out of 5 average rating, 25 reviews

Bayoutiful Getaway

25 Jan – 1 Feb

€ 114 per night
Guest favourite

Farm stay in Odessa

4.98 out of 5 average rating, 46 reviews

The Cabins At Cahaba - Cabin 3

4–11 Dec

€ 101 per night
Guest favourite

Guest house in Palm Harbor

5.0 out of 5 average rating, 25 reviews

Sunny Studio Palm Harbor

10–17 Sep

€ 114 per night
Guest favourite

Guest house in Tampa

5.0 out of 5 average rating, 44 reviews

Peaceful Cottage and Koi Pond Gardens

20–27 Nov

€ 193 per night
Guest favourite

Apartment in Palm Harbor

5.0 out of 5 average rating, 21 reviews

Classy Resort Condo w/ 75 inch TV & Patio

12–19 May

€ 149 per night
Guest favourite

Flat in Palm Harbor

5.0 out of 5 average rating, 28 reviews

Golf & Beach Suite 875 Sq. Ft. Maidstone Building

18–25 Apr

€ 153 per night
Guest favourite

Guest house in Palm Harbor

4.92 out of 5 average rating, 38 reviews

Home away from home

24 Sep – 1 Oct

€ 86 per night
Guest favourite

Cottage in Safety Harbor

5.0 out of 5 average rating, 21 reviews

"Sweet Harbor Cottage" Walk to Downtown

2–9 Jul

€ 156 per night
Guest favourite

Apartment in Palm Harbor

4.97 out of 5 average rating, 31 reviews

Beautiful 1 bedroom Condo / Innisbrook Golf Resort

20–27 Jul

€ 160 per night

Quick stats about holiday 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

€ 18 before taxes and fees

Destinations to explore

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