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
Guest house in Palm Harbor
Home away from home
Check for DISCOUNTS! Private unit has a designated parking spot, pool access, its own water heater, water softener, filtration system, two ceiling fans, & ac/heater. Featuring a queen sleep number bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, & table. The bathroom has a full sized walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more.
24 Nov – 1 Dec
£71 per night
4.91 out of 5 average rating, 35 reviews
Guest favourite
Tiny home in Oldsmar
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.
15–22 JulIndividual Host,
£99 per night
4.96 out of 5 average rating, 237 reviews
Guest favourite
Guest house in Palm Harbor
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.
24–31 JulIndividual Host,
£108 per night
4.97 out of 5 average rating, 190 reviews

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 suite in Oldsmar
Quiet Bay Getaway-Hot Tub-Dog friendly-Bikes
11–18 Apr
£98 per night
4.91 out of 5 average rating, 95 reviews
Guest favourite
Guest house in Oldsmar
salt living at its best
3–10 Sept
£176 per night
4.98 out of 5 average rating, 44 reviews
Guest favourite
Guest house in Tampa
Peaceful Cottage and Koi Pond Gardens
16–23 Nov
£161 per night
5.0 out of 5 average rating, 42 reviews
Superhost
Home in Palm Harbor
Cozy home 15 mins to beach
13–20 Aug
£143 per night
4.96 out of 5 average rating, 23 reviews
Guest favourite
Guest house in Clearwater
Cozy In-Law Suite Near Beach
2–9 Aug
£80 per night
5.0 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Palm Harbor
Classy Resort Condo w/ 75 inch TV & Patio
26 Mar – 2 Apr
£136 per night
5.0 out of 5 average rating, 21 reviews
Guest favourite
Guest house in Tarpon Springs
Bayoutiful Getaway
13–20 Nov
£97 per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Oldsmar
Fountain House On Timberbay Lake
23–30 Apr
£199 per night
4.98 out of 5 average rating, 66 reviews
Guest favourite
Farm stay in Odessa
The Cabins At Cahaba - Cabin 3
4–11 Sept
£86 per night
4.98 out of 5 average rating, 43 reviews
Guest favourite
Guest suite in Odessa
GREAT ESCAPE for the Road Warrior.
26 Nov – 3 Dec
£101 per night
5.0 out of 5 average rating, 71 reviews
Guest favourite
Flat in Palm Harbor
Golf & Beach Suite 875 Sq. Ft. Maidstone Building
1–8 Oct
£126 per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Guest house in Palm Harbor
Sunny Studio Palm Harbor
31 May – 7 Jun
£104 per night
5.0 out of 5 average rating, 23 reviews

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

£16 before taxes and fees

Destinations to explore

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