Holiday houses in Oldsmar

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Top-rated holiday rentals in Oldsmar

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

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Guest favourite

Home in Tampa

4.78 out of 5 average rating, 224 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!

8–15 Jul

$356 NZD per night

Guest favourite

Home in Palm Harbor

4.94 out of 5 average rating, 182 reviews

Private Entrance/Well Appointed Suite/ Lake View

Private entrance/ Private suite/bath w/ walk in closet. Microwave/fridge. Convenient parking. Beautiful view of the lake and all its wildlife. Everything you need to go to the beach is in the room, beach towels, umbrellas, beach mat. Due to host allergies, NO pets/animals/service animals. No smoking/vaping/drinking/drunkenness. Sensitivities? I do not use plug-ins, scented sprays, scented detergents/dryer sheets. If traveling w/ a service animal, kindly, please choose another Airbnb property.

10–17 Oct

$153 NZD per night

Guest favourite

Home in Oldsmar

4.94 out of 5 average rating, 17 reviews

Sunny Oasis: Villa Retreat

Welcome to a stunning 2-bedroom, 2-bathroom villa nestled in the heart of sunny Florida! Whether you're seeking a relaxing beach getaway or exploring all that Florida has to offer, this villa is your perfect destination. Located 15-20 minutes from the beach in a prime location, you'll find a plethora of dining, shopping, and entertainment options nearby, ensuring there's something for everyone to enjoy. Book your stay today and experience the ultimate in comfort, convenience, and coastal charm.

31 Aug – 7 Sep

$309 NZD per night

Guest favourite

Tiny home in Oldsmar

4.95 out of 5 average rating, 244 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.

7–14 Jun

$201 NZD per night

Guest favourite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 198 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.

21–28 Oct

$232 NZD per night

Guest favourite

Farm stay in Odessa

4.98 out of 5 average rating, 173 reviews

Farm and lake stay at Malfini Cay

PRIVATE GUESTHOUSE...Lakefront -full kitchen living room-very large bedroom-full bath-2.5 acres. Newly decorated/remodeled. 2 flat screen TVs-Roku (Netflix and Spectrum app)-WIFI -laminate flooring-high thread count sheets-comfy queen bed. IKEA sleeper sofa in livingroom. All kitchen appliances with coffee bar/Keurig-W/D. Wooded setting-beautiful views of ski lake. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

28 Jul – 4 Aug

$287 NZD per night

Guest favourite

Apartment in Oldsmar

4.92 out of 5 average rating, 59 reviews

Modern 2nd Floor Two Bedroom Apt with Pool

Everything you need in one place! Just 8 miles to Honeymoon Island! Modern and very private two-bedroom second floor in-law suite in private home with kitchen/sitting area, full-size bathroom with shower, and coin operated washer/dryer for use. Guests may use the pool and grill. Private mini dog park with cleanup station and sitting area for smoking. Please note we only allow small pets only. Under 20lbs.

21–28 Jun

$303 NZD per night

Guest favourite

Apartment in Oldsmar

4.86 out of 5 average rating, 21 reviews

Delightful Stay

Welcome to my tranquil Oldsmar Airbnb! Thrilled to invite you to a cozy retreat designed for serene getaways. Discover a quiet ambiance and tastefully furnished space equipped with all essentials for comfort. Excited for you to experience the inviting atmosphere and enjoy prepared amenities. Your comfort is my priority—I eagerly await hosting your unforgettable visit!

4–11 Mar

$162 NZD per night

Guest favourite

Home in Oldsmar

4.85 out of 5 average rating, 67 reviews

Private In-Law Suite with Beautiful Bay View

This is not just a room. It is a beautiful and generous suite with your private living room over looking the old Tampa Bay. In the morning, you can enjoy your coffee while listening to birds singing; in the evening, you can enjoy the sunset on your dinner table. It is minutes from parks, from shopping centers, 15 minutes from beach, and 25 minutes from the airport.

4–11 Dec

$228 NZD per night

Guest favourite

Home in Palm Harbor

4.89 out of 5 average rating, 166 reviews

Cute Lil' House Near Historic Downtown Palm Harbor

They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.

10–17 Aug

$227 NZD per night

Guest favourite

Guesthouse in Odessa

4.87 out of 5 average rating, 315 reviews

Private Guest House

Quiet neighborhood tucked back on a private one-acre lot. The guest house is a great place to hang out, relax, fish or kayak in the lake. However, the beaches and other activities are a short drive away. We are located about 12 miles north of downtown Tampa and 30 miles north of St. Pete. Full kitchen facilities. Very pet friendly.

16–23 Feb

$165 NZD per night

Guest favourite

Guesthouse in Safety Harbor

4.93 out of 5 average rating, 227 reviews

Tiny House Downtown, Superb Location

Despite its size, this tiny home has all you need! This ideal and quiet space is located in downtown Safety Harbor around the corner from Main Street. This light, airy space comes completely equipped to hang out for a while. See what all the tiny home excitement is about!

28 Mar – 4 Apr

$253 NZD per night