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Oldsmar Holiday Rentals

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50 rentals in Oldsmar.
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family friendly, gated community, two pools, lake outside back door., holiday rental in Oldsmar

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW Listing! Serene, Natural Privacy in a Centralized Location, holiday rental in Oldsmar

NEW Listing! Serene, Natural Privacy in a Centralized Location

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Yellow House - 3 Bdr / 2 Bth House w/Pool, holiday rental in Oldsmar

The Yellow House - 3 Bdr / 2 Bth House w/Pool

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Condo on Golf & Country Club in Palm Harbor, holiday rental in Oldsmar

Luxury Condo on Golf & Country Club in Palm Harbor

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pool House near Beaches, holiday rental in Oldsmar

Pool House near Beaches

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Serenity Suite near Tampa's Reigning NFL Superbowl Champion and NHL Stanley Cup, holiday rental in Oldsmar

Serenity Suite near Tampa's Reigning NFL Superbowl Champion and NHL Stanley Cup

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dolphin Bay Retreat, holiday rental in Oldsmar

Dolphin Bay Retreat

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Flamingo Bungalow Beautiful Tampa Retreat, holiday rental in Oldsmar

Flamingo Bungalow Beautiful Tampa Retreat

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Entire Executive Home, Florida Pool Getaway, 1.4 acres in the heart of the City, holiday rental in Oldsmar

Entire Executive Home, Florida Pool Getaway, 1.4 acres in the heart of the City

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Florida Blue House, holiday rental in Oldsmar

Florida Blue House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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La Rustic House, holiday rental in Oldsmar

La Rustic House

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Paradise Oasis-Resort House, holiday rental in Oldsmar

Paradise Oasis-Resort House

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Town & Country & Near Clearwater Beaches, holiday rental in Oldsmar

Town & Country & Near Clearwater Beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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You Are Closer to Your Own Private Paradise on Beautiful Tampa Bay!, holiday rental in Oldsmar

You Are Closer to Your Own Private Paradise on Beautiful Tampa Bay!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Captivating Downtown Safety Harbor Villa - Extended Stay, Corp Housing, Relo's, holiday rental in Oldsmar

Captivating Downtown Safety Harbor Villa - Extended Stay, Corp Housing, Relo's

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Corp Housing, Relo's, Extended Stay, at Seadog Cottages-Pet Friendly, holiday rental in Oldsmar

Corp Housing, Relo's, Extended Stay, at Seadog Cottages-Pet Friendly

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy Beautiful Water Views Front and Back, holiday rental in Oldsmar

Enjoy Beautiful Water Views Front and Back

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Casa la Cala - Serious Fun + Luxury Relaxation!, holiday rental in Oldsmar

Casa la Cala - Serious Fun + Luxury Relaxation!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Executive,4 Brm Home in Quiet Upscale Palm Harbor Florida, holiday rental in Oldsmar

Executive,4 Brm Home in Quiet Upscale Palm Harbor Florida

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly renovated home on the water with heated pool, holiday rental in Oldsmar

Newly renovated home on the water with heated pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Casa del Tren - Rare Availability + Serious Fun!, holiday rental in Oldsmar

Casa del Tren - Rare Availability + Serious Fun!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 2500sqft Palm Harbor Home 5 miles from Beach, holiday rental in Oldsmar

Beautiful 2500sqft Palm Harbor Home 5 miles from Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Blue - A True Rare Find! 1 mile to Waterfront, holiday rental in Oldsmar

Casa Blue - A True Rare Find! 1 mile to Waterfront

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious 1 bedroom Suite with King Bed in quaint Safety Harbor, holiday rental in Oldsmar

Spacious 1 bedroom Suite with King Bed in quaint Safety Harbor

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated, Walk To Bay And Park, Pet Friendly, holiday rental in Oldsmar

Newly Renovated, Walk To Bay And Park, Pet Friendly

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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House of Relaxation, close to great beaches, holiday rental in Oldsmar

House of Relaxation, close to great beaches

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy quite cottage nestled in Safety Harbor, holiday rental in Oldsmar

Cozy quite cottage nestled in Safety Harbor

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private Home minutes from beaches, holiday rental in Oldsmar

Private Home minutes from beaches

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Casa Artista - The Most Enchanting, Relaxing Escape!, holiday rental in Oldsmar

Casa Artista - The Most Enchanting, Relaxing Escape!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Safety Harbor Bird House with Lake View, holiday rental in Oldsmar

Safety Harbor Bird House with Lake View

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palm Harbor Family Residential Resort Style Living, holiday rental in Oldsmar

Palm Harbor Family Residential Resort Style Living

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gulf Coast Woodland Retreat by Golf & Country Club, holiday rental in Oldsmar

Gulf Coast Woodland Retreat by Golf & Country Club

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great home in a nice, quiet neighborhood., holiday rental in Oldsmar

Great home in a nice, quiet neighborhood.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tampa TreeHouse, holiday rental in Oldsmar

Tampa TreeHouse

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private cottage by the Sea, holiday rental in Oldsmar

Private cottage by the Sea

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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CLEARWATER FL 2 Bedroom 2 Bathroom Furnished Condo, holiday rental in Oldsmar

CLEARWATER FL 2 Bedroom 2 Bathroom Furnished Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tarpon Woods Condo with Lake View, holiday rental in Oldsmar

Tarpon Woods Condo with Lake View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pete & Ron's Fun House, holiday rental in Oldsmar

Pete & Ron's Fun House

8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Safety Harbor Getaway Villa with Pool, holiday rental in Oldsmar

Safety Harbor Getaway Villa with Pool

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Relaxation at the Tropical Pool House, holiday rental in Oldsmar

Relaxation at the Tropical Pool House

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Single Family Home with Private Heated Pool near Safety Harbor, holiday rental in Oldsmar

Single Family Home with Private Heated Pool near Safety Harbor

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Welcome to the Mar Bay Motel & Suites, holiday rental in Oldsmar

Welcome to the Mar Bay Motel & Suites

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Enjoy Unlimited Free Golf, Near Top-rated Beaches, Dec. Special!, holiday rental in Oldsmar

Enjoy Unlimited Free Golf, Near Top-rated Beaches, Dec. Special!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet-Friendly Home w/ Fire Pit -  10 Mins to Gulf!, holiday rental in Oldsmar

Pet-Friendly Home w/ Fire Pit - 10 Mins to Gulf!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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East Lake Gem on the Green, holiday rental in Oldsmar

East Lake Gem on the Green

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sensational Condo, holiday rental in Oldsmar

Sensational Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Safety Harbor Home w/ Fire Pit, 1 Mi to Pier!, holiday rental in Oldsmar

NEW! Safety Harbor Home w/ Fire Pit, 1 Mi to Pier!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Villa Resort House, holiday rental in Oldsmar

Luxury Villa Resort House

5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Bahama Breeze Resort House, holiday rental in Oldsmar

Bahama Breeze Resort House

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Town & Country & Near Clearwater Beaches, holiday rental in Oldsmar

Town & Country & Near Clearwater Beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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