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
*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!
8–15 Jun
$238 SGD per night
4.78 out of 5 average rating, 221 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.
10–17 Nov
$123 SGD 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.
3–10 Sep
$137 SGD 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
Cottage in Dunedin
BeachBunkies Cottage 1. Four miles to the beach!
1–8 Sep
$110 SGD per night
4.96 out of 5 average rating, 74 reviews
Guest favourite
Guest house in Tampa
Peaceful Cottage and Koi Pond Gardens
16–23 Nov
$190 SGD per night
5.0 out of 5 average rating, 42 reviews
Guest favourite
Guest house in Oldsmar
salt living at its best
6–13 Sep
$221 SGD per night
4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in Oldsmar
Fountain House On Timberbay Lake
23–30 Apr
$248 SGD per night
4.98 out of 5 average rating, 66 reviews
Guest favourite
Home in Oldsmar
Tropical Vacay pool home
22–29 Oct
$270 SGD per night
4.9 out of 5 average rating, 29 reviews
Guest favourite
Home in Oldsmar
Modern & Spacious Retreat with Private Pool!
16–23 Feb
$302 SGD per night
4.85 out of 5 average rating, 48 reviews
Guest favourite
Home in Oldsmar
Beach Front | Amazing Views | Bikes | Kayaks WOW
11–18 Jul
$609 SGD per night
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Palm Harbor
Cozy home 15 mins to beach
23–30 Aug
$175 SGD per night
4.96 out of 5 average rating, 23 reviews
Guest favourite
Apartment in Palm Harbor
Classy Resort Condo w/ 75 inch TV & Patio
26 Mar – 2 Apr
$163 SGD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Guest house in Tarpon Springs
Bayoutiful Getaway
4–11 Dec
$120 SGD per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Farm stay in Odessa
The Cabins At Cahaba - Cabin 3
13–20 Oct
$106 SGD per night
4.98 out of 5 average rating, 43 reviews
Guest favourite
Apartment in Oldsmar
NEW- Waterview- 2 bed/2 bath condo w/pool
13–20 May
$228 SGD per night
4.94 out of 5 average rating, 16 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

$27 SGD before taxes and fees

Destinations to explore

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