Oldsmar vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Oldsmar

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Palm Harbor

4.94 out of 5 average rating, 183 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.

Oct 28 – Nov 4

G$16,951 GYD per night

Guest favorite

Tiny home in Oldsmar

4.96 out of 5 average rating, 246 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.

Aug 16 – 23

G$20,723 GYD per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 199 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.

Apr 4 – 11

G$24,470 GYD per night

Guest favorite

Guest suite in Tarpon Springs

4.95 out of 5 average rating, 107 reviews

Private suite in heart of Tarpon Springs!

House centrally located in a safe, residential area. Enjoy a clean, cozy & comfortable private suite with private entrance! Next to Downtown Tarpon, Tarpon Springs Sponge Docks, Sunset Beach, Safety Harbor, and many other attractions. Less than 5 minutes from the beach! Enjoy fast wifi, cable, and a cozy queen bed! Full kitchen. During your stay you’ll have access to bicycles, plenty of beach towels, hats, beach toys. Beach chairs, chairs umbrellas, small cooler and a variety of sunscreens

Sep 21 – 28

G$17,882 GYD per night

Guest favorite

Guest suite in Dunedin

4.94 out of 5 average rating, 202 reviews

Downtown Coastal Studio

Our Downtown Coastal Studio was recently renovated. The studio has a bright and airy atmosphere. Both clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin and two blocks to the Pinellas Trail. Simply park your car and enjoy downtown on foot or rent a bike and cruise around. We are close to two major beaches, the marina, and John G. Hubbard Park, which is just across the street with a nice path to stroll along the water or take in the sunset.

Jul 22 – 29

G$20,393 GYD per night

Guest favorite

Apartment in Tampa

4.92 out of 5 average rating, 117 reviews

Stunning Studio in Citrus Park

My beautiful studio apartment is nestled in the heart of Citrus Park/ Carrollwood area. We are walking distance from shops and restaurant. This cozy and spacious studio has a fully equipped kitchen (Keurig coffee maker and complementary coffee, toaster, pots and pans and utensils). The full bathroom has a stand up shower (shampoo, conditioner, and body wash provided). The studio has a private entrance and self check-in for your convenience. **** One parking space available per reservation*

May 3 – 10

G$17,314 GYD per night

Guest favorite

Guest suite in Tampa

4.98 out of 5 average rating, 121 reviews

The Little Oasis Suite. #2

A modern, cozy, and fresh suite, with private kitchen and bathroom inside the room. The kitchen is equipped with a coffee maker, tea kettle, toaster, and induction stove, ideal for preparing breakfast. With independent entrance, apart from the main house (shared with other guests). Free parking on premises. It’s located 11 minutes from the Tampa International Airport and near the Citrus Park international mall. There are several restaurants and shops nearby👉regular time not overnight

Sep 14 – 21

G$15,654 GYD per night

Guest favorite

Apartment in Tampa

4.95 out of 5 average rating, 268 reviews

Private and cozy studio close to the Airport

This apartment is amazing ,completely remodeled and luxury , fantastic location! , fast internet .Very comfortable to work , quiet neighborhood. The apartment is equipped with everything you could need. Completely private with separate entrance ,without any connection to the main house. Very clean, fresh decoration to spend a beautiful vacation. (Approximately 40 minutes away from Clearwater beach) This apartment is close to supermarkets, attractions and downtown. We are available 24/7

Aug 18 – 25

G$16,571 GYD per night

Guest favorite

Farm stay in Odessa

4.99 out of 5 average rating, 288 reviews

Farm and lake stay at Maison de L'eau Douce

LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Aug 2 – 9

G$30,073 GYD per night

Guest favorite

Home in Tarpon Springs

4.95 out of 5 average rating, 175 reviews

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. The lower is an office for the maintenance team. No smoking, vaping, or illegal drugs permitted.

Aug 10 – 17

G$23,911 GYD per night

Guest favorite

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.

Dec 7 – 14

G$27,660 GYD per night

Guest favorite

Guesthouse in Odessa

4.87 out of 5 average rating, 317 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.

Nov 3 – 10

G$18,625 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oldsmar vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oldsmar's top sights

Mease Countryside Hospital6 locals recommend

Philippe Park60 locals recommend

Oldsmar Flea Market33 locals recommend

Walmart Supercenter13 locals recommend

Empower Adventures Tampa Bay29 locals recommend

AMC Woodlands Square 2024 locals recommend

Other great vacation rentals in Oldsmar

Guest favorite

Apartment in Oldsmar

4.86 out of 5 average rating, 22 reviews

Delightful Stay

Apr 3 – 10

G$17,235 GYD per night

Guest favorite

Home in Oldsmar

4.85 out of 5 average rating, 67 reviews

Private In-Law Suite with Beautiful Bay View

Sep 22 – 29

G$23,085 GYD per night

Guest favorite

Home in Oldsmar

4.94 out of 5 average rating, 17 reviews

Sunny Oasis: Villa Retreat

Jan 6 – 13

G$29,752 GYD per night

Guest favorite

Guest suite in Oldsmar

4.87 out of 5 average rating, 97 reviews

Quiet Bay Getaway-Hot Tub-Dog friendly-Bikes

May 6 – 13

G$21,518 GYD per night

Superhost

Home in Oldsmar

4.89 out of 5 average rating, 96 reviews

Coastal themed home near beach and airport

Mar 27 – Apr 3

G$29,598 GYD per night

Guest favorite

Apartment in Oldsmar

4.92 out of 5 average rating, 60 reviews

Modern 2nd Floor Two Bedroom Apt with Pool

Jul 14 – 21

G$31,245 GYD per night

Guest favorite

Guesthouse in Clearwater

5.0 out of 5 average rating, 23 reviews

Cozy In-Law Suite Near Beach

Aug 6 – 13

G$16,118 GYD per night

Guest favorite

Cottage in Dunedin

4.95 out of 5 average rating, 97 reviews

BeachBunkies Cottage 2. Four miles to the beach!

Apr 15 – 22

G$17,372 GYD per night

Show all

Other great vacation rentals in Oldsmar

Guest favorite

Barn in Odessa

5.0 out of 5 average rating, 27 reviews

Cypress Lakes Barndominium

Jan 28 – Feb 4

G$22,526 GYD per night

Guest favorite

Guest suite in Odessa

5.0 out of 5 average rating, 73 reviews

GREAT ESCAPE for the Road Warrior.

Oct 15 – 22

G$21,575 GYD per night

Guest favorite

Cottage in Safety Harbor

5.0 out of 5 average rating, 27 reviews

"Sweet Harbor Cottage" Walk to Downtown

Jun 9 – 16

G$27,569 GYD per night

Guest favorite

Apartment in Clearwater

5.0 out of 5 average rating, 28 reviews

Welcome to your cozy studio!

Dec 31 – Jan 7

G$17,130 GYD per night

Guest favorite

Apartment in Palm Harbor

5.0 out of 5 average rating, 31 reviews

Golf & Beach Suite 875 Sq. Ft. Maidstone Building

May 30 – Jun 6

G$27,128 GYD per night

Guest favorite

Guesthouse in Palm Harbor

5.0 out of 5 average rating, 32 reviews

Sunny Studio Palm Harbor

Jun 19 – 26

G$21,895 GYD per night

Guest favorite

Cottage in Safety Harbor

5.0 out of 5 average rating, 68 reviews

The Sunshine Cottage - Like Grandma's with WIFI

May 8 – 13

G$23,472 GYD per night

Guest favorite

Condo in Oldsmar

4.94 out of 5 average rating, 17 reviews

NEW- Waterview- 2 bed/2 bath condo w/pool

Sep 27 – Oct 4

G$41,143 GYD per night

Show all

Quick stats about vacation rentals in Oldsmar

Total rentals
120 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
3.7K reviews
Nightly prices starting at
G$4,170 GYD 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 170 vacation rentals in Bridlewood, over 170 vacation rentals in East Lake Woodlands, and over 520 vacation rentals in The Grove Of Laforest.
Are there pet-friendly vacation rentals in Oldsmar?
Four-legged friends are welcome in Oldsmar. Choose from more than 50 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 60 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 70 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 70 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 70 homes with air conditioning, over 30 homes with a bbq area, over 70 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Oldsmar vacation rentals

Top-rated vacation rentals in Oldsmar

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Oldsmar vacation rentals

Stay near Oldsmar's top sights

Other great vacation rentals in Oldsmar

Apartment in Oldsmar

Home in Oldsmar

Home in Oldsmar

Guest suite in Oldsmar

Home in Oldsmar

Apartment in Oldsmar

Guesthouse in Clearwater

Cottage in Dunedin

Other great vacation rentals in Oldsmar

Barn in Odessa

Guest suite in Odessa

Cottage in Safety Harbor

Apartment in Clearwater

Apartment in Palm Harbor

Guesthouse in Palm Harbor

Cottage in Safety Harbor

Condo in Oldsmar

Quick stats about vacation rentals in Oldsmar

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Oldsmar?

Are there pet-friendly vacation rentals in Oldsmar?

Are there vacation rentals with a dedicated workspace in Oldsmar?

Are there Oldsmar vacation rentals on Airbnb with pools?

Do house rentals in Oldsmar have a bbq area?

Do house rentals in Oldsmar have air conditioning?

Do house rentals in Oldsmar have wireless internet?

How much does it cost to stay in house rentals in Oldsmar?

Are there family-friendly house rentals in Oldsmar?

What are the most popular amenities for House Rentals in Oldsmar?

Destinations to explore