Vacation rentals in Oldsmar, FL

Best Vacation rentals and Airbnb offers in Oldsmar, FL

PineCone Cabin Getaway near Natl Park

Cabin, Oldsmar

PineCone Cabin Getaway near Natl Park is a cabin in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About PineCone Cabin Getaway near Natl Park

PineCone Cabin Getaway near Natl Park is a cabin in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $468.

From$48/night

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Wildwood Studio Your Stylish Nature Escape Awaits!

Holiday Home, Oldsmar

Wildwood Studio Your Stylish Nature Escape Awaits! is a holiday home in Oldsmar. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Wildwood Studio Your Stylish Nature Escape Awaits!

Wildwood Studio Your Stylish Nature Escape Awaits! is a holiday home in Oldsmar. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: internet, non smoking, and wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $591.

From$61/night

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Beautiful Condo in prime Florida location within premier gated community.

Condo, Oldsmar

Beautiful Condo in prime Florida location within premier gated community. is a condo in Oldsmar, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful Condo in prime Florida location within premier gated community.

Beautiful Condo in prime Florida location within premier gated community. is a condo in Oldsmar, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $783.

From$75/night

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family friendly, gated community, two pools, lake outside back door.

Condo, Oldsmar

family friendly, gated community, two pools, lake outside back door. is a condo in Oldsmar, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About family friendly, gated community, two pools, lake outside back door.

family friendly, gated community, two pools, lake outside back door. is a condo in Oldsmar, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $917.

From$86/night

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Browse Vacation Rentals with a Pool in Oldsmar, FL

Add a pool to the search when you want an easy place to cool off between outings.

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access

Apartment, Oldsmar

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access is a apartment in Oldsmar, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access is a apartment in Oldsmar, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $665.

From$73/night

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Private Home Away from Home

Apartment, Oldsmar

Private Home Away from Home is a apartment in Oldsmar, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Private Home Away from Home

Private Home Away from Home is a apartment in Oldsmar, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $816.

From$77/night

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Near Fishing: Palm Harbor Studio w/ Pool Access!

Apartment, Oldsmar

Near Fishing: Palm Harbor Studio w/ Pool Access! is a apartment in Oldsmar, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Near Fishing: Palm Harbor Studio w/ Pool Access!

Near Fishing: Palm Harbor Studio w/ Pool Access! is a apartment in Oldsmar, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $934.

From$79/night

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6 Mi to Honeymoon Island: Studio w/ Pool Access

Apartment, Oldsmar

6 Mi to Honeymoon Island: Studio w/ Pool Access is a apartment in Oldsmar, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 6 Mi to Honeymoon Island: Studio w/ Pool Access

6 Mi to Honeymoon Island: Studio w/ Pool Access is a apartment in Oldsmar, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,015.

From$91/night

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Best Oldsmar, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Chic studio with WiFi and AC in cool Tampa

Apartment, Oldsmar

Chic studio with WiFi and AC in cool Tampa is a apartment in Oldsmar, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Chic studio with WiFi and AC in cool Tampa

Chic studio with WiFi and AC in cool Tampa is a apartment in Oldsmar, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $623.

From$62/night

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Canopy Cabana | Luxury Apt, Steps from Main St

Apartment, Oldsmar

Canopy Cabana · Luxury Apt, Steps from Main St is a apartment in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Canopy Cabana | Luxury Apt, Steps from Main St

Canopy Cabana · Luxury Apt, Steps from Main St is a apartment in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,283.

From$113/night

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Cozy creative getaway guesthouse

Guest House, Oldsmar

Cozy creative getaway guesthouse is a guest house in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy creative getaway guesthouse

Cozy creative getaway guesthouse is a guest house in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,084.

From$117/night

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Newly Renovated Apt in Stunning Safety Harbor!

Apartment, Oldsmar

Newly Renovated Apt in Stunning Safety Harbor! is a apartment in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Newly Renovated Apt in Stunning Safety Harbor!

Newly Renovated Apt in Stunning Safety Harbor! is a apartment in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,233.

From$124/night

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Best Pet-Friendly Vacation Rentals in Oldsmar, FL

Bring your pet along with stays that welcome four-legged travelers.

Happy Place B . Such a house

Holiday Home, Oldsmar

Happy Place B . Such a house is a holiday home in Oldsmar, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Happy Place B . Such a house

Happy Place B . Such a house is a holiday home in Oldsmar, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $861.

From$87/night

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Pond front groundfloor 2/2 condo

Condo, Oldsmar

Pond front groundfloor 2/2 condo is a condo in Oldsmar, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Pond front groundfloor 2/2 condo

Pond front groundfloor 2/2 condo is a condo in Oldsmar, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,209.

From$125/night

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The Villa at Harbor House

Villa, Oldsmar

The Villa at Harbor House is a villa in Oldsmar, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Villa at Harbor House

The Villa at Harbor House is a villa in Oldsmar, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,290.

From$134/night

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Casa Artista - A Most Enchanting, Relaxing Escape

Holiday Home, Oldsmar

Casa Artista - A Most Enchanting, Relaxing Escape is a holiday home in Oldsmar, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Casa Artista - A Most Enchanting, Relaxing Escape

Casa Artista - A Most Enchanting, Relaxing Escape is a holiday home in Oldsmar, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,395.

From$135/night

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Best Oldsmar, FL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Private Studio with Patio and Parking

Apartment, Oldsmar

Private Studio with Patio and Parking is a apartment in Oldsmar, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Studio with Patio and Parking

Private Studio with Patio and Parking is a apartment in Oldsmar, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $610.

From$62/night

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Tropical Pardise A

Holiday Home, Oldsmar

Tropical Pardise A is a holiday home in Oldsmar, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Tropical Pardise A

Tropical Pardise A is a holiday home in Oldsmar, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $854.

From$86/night

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Beautifully, Renovated Home in Quiet Cul de Sac! Close to EVERYTHING!

Holiday Home, Oldsmar

Beautifully, Renovated Home in Quiet Cul de Sac! Close to EVERYTHING! is a holiday home in Oldsmar, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Beautifully, Renovated Home in Quiet Cul de Sac! Close to EVERYTHING!

Beautifully, Renovated Home in Quiet Cul de Sac! Close to EVERYTHING! is a holiday home in Oldsmar, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,432.

From$140/night

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Beautiful Villa! On Wildlife Area, Natural Privacy! Close to Everything. Welcome

Villa, Oldsmar

Beautiful Villa! On Wildlife Area, Natural Privacy! Close to Everything. Welcome is a villa in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful Villa! On Wildlife Area, Natural Privacy! Close to Everything. Welcome

Beautiful Villa! On Wildlife Area, Natural Privacy! Close to Everything. Welcome is a villa in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,409.

From$140/night

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Our Favorite Family-Friendly Vacation Rentals in Oldsmar, FL

Plan a trip with stays that give families more room to spread out.

Charming 3-bedroom 2 bath cottage completed remodel Clearwater near the beach

Holiday Home, Oldsmar

Charming 3-bedroom 2 bath cottage completed remodel Clearwater near the beach is a holiday home in Oldsmar, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Charming 3-bedroom 2 bath cottage completed remodel Clearwater near the beach

Charming 3-bedroom 2 bath cottage completed remodel Clearwater near the beach is a holiday home in Oldsmar, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,353.

From$118/night

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Charming Villa in Safety Harbor for the Family

Villa, Oldsmar

Charming Villa in Safety Harbor for the Family is a villa in Oldsmar, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Charming Villa in Safety Harbor for the Family

Charming Villa in Safety Harbor for the Family is a villa in Oldsmar, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,242.

From$121/night

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Farm and lake stay at Maison De L'eau Douce

Cottage, Oldsmar

Farm and lake stay at Maison De L'eau Douce is a cottage in Oldsmar, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Farm and lake stay at Maison De L'eau Douce

Farm and lake stay at Maison De L'eau Douce is a cottage in Oldsmar, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,181.

From$125/night

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Luxury 1-bedroom cottage with pool in prime location. Peaceful resort style.

Holiday Home, Oldsmar

Luxury 1-bedroom cottage with pool in prime location. Peaceful resort style. is a holiday home in Oldsmar, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Luxury 1-bedroom cottage with pool in prime location. Peaceful resort style.

Luxury 1-bedroom cottage with pool in prime location. Peaceful resort style. is a holiday home in Oldsmar, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,221.

From$127/night

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