Vacation rentals in Oldsmar, FL

46 available vacation rental offers

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Best vacation rentals and Airbnb offers in Oldsmar, FL

Vibrant 2BR 2BA w King Bed Pool Gym 11 - Oldsmar, FL
10 ★ 1 reviews

Vibrant 2BR 2BA w King Bed Pool Gym 11

Apartment, Oldsmar

Vibrant 2BR 2BA w King Bed Pool Gym 11 is a apartment in Oldsmar, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Vibrant 2BR 2BA w King Bed Pool Gym 11

Vibrant 2BR 2BA w King Bed Pool Gym 11 is a apartment in Oldsmar, with pool access, parking, 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, parking, and street parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,491.

From$166/night
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Serenity on the Sea Luxury Condo w Prvt Balcony - Oldsmar, FL
9 ★ 4 reviews

Serenity on the Sea Luxury Condo w Prvt Balcony

Apartment, Oldsmar

Serenity on the Sea Luxury Condo w Prvt Balcony is a apartment in Oldsmar, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring…

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About Serenity on the Sea Luxury Condo w Prvt Balcony

Serenity on the Sea Luxury Condo w Prvt Balcony is a apartment in Oldsmar, with pool access, easy beach access, and outdoor space. 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, beachfront, and beach front.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,476.

From$171/night
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The Hemingway - Oldsmar, FL
8.2 ★ 26 reviews

The Hemingway

Apartment, Oldsmar

The Hemingway is a apartment in Oldsmar, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About The Hemingway

The Hemingway is a apartment in Oldsmar, with 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: free cancellation, pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,255.

From$124/night
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Sunset on the Bay Designer Condo Private Balcony - Oldsmar, FL
8 ★ 2 reviews

Sunset on the Bay Designer Condo Private Balcony

Apartment, Oldsmar

Sunset on the Bay Designer Condo Private Balcony is a apartment in Oldsmar, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Sunset on the Bay Designer Condo Private Balcony

Sunset on the Bay Designer Condo Private Balcony is a apartment in Oldsmar, with easy beach access, outdoor space, and 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 wifi, beachfront, beach front, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,420.

From$164/night
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Family-friendly vacation rentals in Oldsmar, FL

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

Tampa Home w/ Private Backyard ~ 15 Mi to Downtown - Oldsmar, FL

Tampa Home w/ Private Backyard ~ 15 Mi to Downtown

Cottage, Oldsmar

Tampa Home w/ Private Backyard ~ 15 Mi to Downtown is a cottage in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Tampa Home w/ Private Backyard ~ 15 Mi to Downtown

Tampa Home w/ Private Backyard ~ 15 Mi to Downtown is a cottage 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,881.

From$193/night
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Poolside Oasis! Family Escape in Safety Harbor - Oldsmar, FL

Poolside Oasis! Family Escape in Safety Harbor

Cottage, Oldsmar

Poolside Oasis! Family Escape in Safety Harbor is a cottage in Oldsmar, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Poolside Oasis! Family Escape in Safety Harbor

Poolside Oasis! Family Escape in Safety Harbor is a cottage in Oldsmar, with pet-friendly space, pool 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, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,411.

From$248/night
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8 Mi to Tarpon Springs Sponge Docks: Gem w/ Games - Oldsmar, FL

8 Mi to Tarpon Springs Sponge Docks: Gem w/ Games

Cottage, Oldsmar

8 Mi to Tarpon Springs Sponge Docks: Gem w/ Games is a cottage in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 8 Mi to Tarpon Springs Sponge Docks: Gem w/ Games

8 Mi to Tarpon Springs Sponge Docks: Gem w/ Games is a cottage 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,925.

From$272/night
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1465 Satsuma Street - Oldsmar, FL

1465 Satsuma Street

Cottage, Oldsmar

1465 Satsuma Street is a cottage in Oldsmar, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About 1465 Satsuma Street

1465 Satsuma Street is a cottage in Oldsmar, with 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, kitchen, with kitchen, and dryer.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $16,791.

From$2,053/night
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Pet-friendly vacation rentals in Oldsmar, FL

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

Charming Vacation House 3Be 2Ba Solar heated pool - Oldsmar, FL

Charming Vacation House 3Be 2Ba Solar heated pool

Villa, Oldsmar

Charming Vacation House 3Be 2Ba Solar heated pool is a villa in Oldsmar, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Vacation House 3Be 2Ba Solar heated pool

Charming Vacation House 3Be 2Ba Solar heated pool is a villa in Oldsmar, with pool access and parking. 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, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,613.

From$298/night
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8 Mi to Honeymoon Island: Golf Getaway w/ Balcony! - Oldsmar, FL

8 Mi to Honeymoon Island: Golf Getaway w/ Balcony!

Apartment, Oldsmar

8 Mi to Honeymoon Island: Golf Getaway w/ Balcony! is a apartment in Oldsmar, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About 8 Mi to Honeymoon Island: Golf Getaway w/ Balcony!

8 Mi to Honeymoon Island: Golf Getaway w/ Balcony! is a apartment in Oldsmar, with pet-friendly space, outdoor 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,293.

From$132/night
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Historic Haven by Downtown Safety Harbor - Oldsmar, FL

Historic Haven by Downtown Safety Harbor

Holiday Home, Oldsmar

Historic Haven by Downtown Safety Harbor is a holiday home in Oldsmar, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Historic Haven by Downtown Safety Harbor

Historic Haven by Downtown Safety Harbor is a holiday home in Oldsmar, with pet-friendly space and 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, pet friendly, pets friendly, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,795.

From$181/night
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Historic 4B Sleeps 8 Backyard Firepit Bikes - Oldsmar, FL

Historic 4B Sleeps 8 Backyard Firepit Bikes

Holiday Home, Oldsmar

Historic 4B Sleeps 8 Backyard Firepit Bikes is a holiday home in Oldsmar, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Historic 4B Sleeps 8 Backyard Firepit Bikes

Historic 4B Sleeps 8 Backyard Firepit Bikes is a holiday home in Oldsmar, with pet-friendly space, parking, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,814.

From$189/night
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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.

The Hemingway 2bd Tropical Elegance on the Water - Oldsmar, FL
8 ★ 2 reviews

The Hemingway 2bd Tropical Elegance on the Water

Apartment, Oldsmar

The Hemingway 2bd Tropical Elegance on the Water is a apartment in Oldsmar, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About The Hemingway 2bd Tropical Elegance on the Water

The Hemingway 2bd Tropical Elegance on the Water is a apartment in Oldsmar, with pool access and easy beach 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, beachfront, and beach front.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,626.

From$189/night
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Pearl Suite a Balcony Bayview Suite Htd Pool - Oldsmar, FL
6 ★ 1 reviews

Pearl Suite a Balcony Bayview Suite Htd Pool

Apartment, Oldsmar

Pearl Suite a Balcony Bayview Suite Htd Pool is a apartment in Oldsmar, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring…

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About Pearl Suite a Balcony Bayview Suite Htd Pool

Pearl Suite a Balcony Bayview Suite Htd Pool is a apartment in Oldsmar, with pool access, easy beach access, and outdoor space. 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, bbq facilities, and internet.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,438.

From$167/night
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Modern 2BR 2BA King Bed Pool Gym 6 - Oldsmar, FL

Modern 2BR 2BA King Bed Pool Gym 6

Apartment, Oldsmar

Modern 2BR 2BA King Bed Pool Gym 6 is a apartment in Oldsmar, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Modern 2BR 2BA King Bed Pool Gym 6

Modern 2BR 2BA King Bed Pool Gym 6 is a apartment in Oldsmar, with pool access, parking, 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, parking, and street parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,485.

From$165/night
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Modern 2BR 2BA King Bed Pool Gym 7 - Oldsmar, FL

Modern 2BR 2BA King Bed Pool Gym 7

Apartment, Oldsmar

Modern 2BR 2BA King Bed Pool Gym 7 is a apartment in Oldsmar, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern 2BR 2BA King Bed Pool Gym 7

Modern 2BR 2BA King Bed Pool Gym 7 is a apartment in Oldsmar, with pool access, parking, 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, parking, and street parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,485.

From$165/night
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Vacation rentals with parking in Oldsmar, FL

Find vacation rentals that make arriving by car easier.

Pasture & Pond Views: Lovely Lutz Apartment - Oldsmar, FL
4 ★ 1 reviews

Pasture & Pond Views: Lovely Lutz Apartment

Apartment, Oldsmar

Pasture & Pond Views: Lovely Lutz Apartment is a apartment in Oldsmar, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Pasture & Pond Views: Lovely Lutz Apartment

Pasture & Pond Views: Lovely Lutz Apartment 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,352.

From$144/night
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Pine Street - Oldsmar, FL

Pine Street

Holiday Home, Oldsmar

Pine Street is a holiday home in Oldsmar, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pine Street

Pine Street is a holiday home 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, free wifi, parking, paid parking, and ac.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,222.

From$140/night
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Forever Beach View Sailport Resort Condos Tampa - Oldsmar, FL

Forever Beach View Sailport Resort Condos Tampa

Holiday Home, Oldsmar

Forever Beach View Sailport Resort Condos Tampa is a holiday home in Oldsmar, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Forever Beach View Sailport Resort Condos Tampa

Forever Beach View Sailport Resort Condos Tampa is a holiday home in Oldsmar, with pool access, easy beach access, and 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, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,596.

From$174/night
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Spacious 3BR 2BA w Pool Gym Near Airport 4 - Oldsmar, FL

Spacious 3BR 2BA w Pool Gym Near Airport 4

Apartment, Oldsmar

Spacious 3BR 2BA w Pool Gym Near Airport 4 is a apartment in Oldsmar, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious 3BR 2BA w Pool Gym Near Airport 4

Spacious 3BR 2BA w Pool Gym Near Airport 4 is a apartment in Oldsmar, with pool access, parking, 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, parking, and street parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,744.

From$188/night
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