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Oldsmar Holiday Apartments

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39 rentals in Oldsmar.
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family friendly, gated community, two pools, lake outside back door.

Condo/Apartment
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, holiday rental in Oldsmar
NEW Listing! Serene, Natural Privacy in a Centralized Location, holiday rental in Oldsmar

NEW Listing! Serene, Natural Privacy in a Centralized Location

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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TreeHouse in Tampa, holiday rental in Oldsmar
TreeHouse in Tampa, holiday rental in Oldsmar
TreeHouse in Tampa, holiday rental in Oldsmar

TreeHouse in Tampa

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Centrally located to beaches,   Close to Bush Gardens Pets Welcome  Free Wifi, holiday rental in Oldsmar
Centrally located to beaches,   Close to Bush Gardens Pets Welcome  Free Wifi, holiday rental in Oldsmar
Centrally located to beaches,   Close to Bush Gardens Pets Welcome  Free Wifi, holiday rental in Oldsmar

Centrally located to beaches, Close to Bush Gardens Pets Welcome Free Wifi

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Home in Quiet Cul de Sac! Close to EVERYTHING, holiday rental in Oldsmar
Beautiful Home in Quiet Cul de Sac! Close to EVERYTHING, holiday rental in Oldsmar
Beautiful Home in Quiet Cul de Sac! Close to EVERYTHING, holiday rental in Oldsmar

Beautiful Home in Quiet Cul de Sac! Close to EVERYTHING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Pete's Place 9 Bedroom 7 Bath Tampa Resort, holiday rental in Oldsmar
Pete's Place 9 Bedroom 7 Bath Tampa Resort, holiday rental in Oldsmar
Pete's Place 9 Bedroom 7 Bath Tampa Resort, holiday rental in Oldsmar

Pete's Place 9 Bedroom 7 Bath Tampa Resort

Holiday Rental House
9 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Stunning Key West Style Waterfront Home with Exceptional Views, holiday rental in Oldsmar
Stunning Key West Style Waterfront Home with Exceptional Views, holiday rental in Oldsmar
Stunning Key West Style Waterfront Home with Exceptional Views, holiday rental in Oldsmar

Stunning Key West Style Waterfront Home with Exceptional Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pond front groundfloor 2/2 condo, holiday rental in Oldsmar
Pond front groundfloor 2/2 condo, holiday rental in Oldsmar
Pond front groundfloor 2/2 condo, holiday rental in Oldsmar

Pond front groundfloor 2/2 condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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STUNNING WATERFRONT RESORT EXPERIENCE!, holiday rental in Oldsmar
STUNNING WATERFRONT RESORT EXPERIENCE!, holiday rental in Oldsmar
STUNNING WATERFRONT RESORT EXPERIENCE!, holiday rental in Oldsmar

STUNNING WATERFRONT RESORT EXPERIENCE!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Summer Beach Getaway - Private Pool Home/Dog Friendly, holiday rental in Oldsmar
Summer Beach Getaway - Private Pool Home/Dog Friendly, holiday rental in Oldsmar
Summer Beach Getaway - Private Pool Home/Dog Friendly, holiday rental in Oldsmar

Summer Beach Getaway - Private Pool Home/Dog Friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular New House, Close to Safety Harbor, Dunedin, Beaches &, Shopping!, holiday rental in Oldsmar
Spectacular New House, Close to Safety Harbor, Dunedin, Beaches &, Shopping!, holiday rental in Oldsmar
Spectacular New House, Close to Safety Harbor, Dunedin, Beaches &, Shopping!, holiday rental in Oldsmar

Spectacular New House, Close to Safety Harbor, Dunedin, Beaches &, Shopping!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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, holiday rental in Oldsmar
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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pool House near Beaches, holiday rental in Oldsmar
Pool House near Beaches, holiday rental in Oldsmar
Pool House near Beaches, holiday rental in Oldsmar

Pool House near Beaches

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Central to everything Tampa Bay!, holiday rental in Oldsmar
Central to everything Tampa Bay!, holiday rental in Oldsmar
Central to everything Tampa Bay!, holiday rental in Oldsmar

Central to everything Tampa Bay!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright two story townhome, holiday rental in Oldsmar
Bright two story townhome, holiday rental in Oldsmar
Bright two story townhome, holiday rental in Oldsmar

Bright two story townhome

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Tranquil and Zen and Convenient to Everything, holiday rental in Oldsmar
Tranquil and Zen and Convenient to Everything, holiday rental in Oldsmar
Tranquil and Zen and Convenient to Everything, holiday rental in Oldsmar

Tranquil and Zen and Convenient to Everything

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Condo Gulf Coast Florida

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Cottage on Rocky Creek - Rate Inclusive of all fees, holiday rental in Oldsmar
Waterfront Cottage on Rocky Creek - Rate Inclusive of all fees, holiday rental in Oldsmar
Waterfront Cottage on Rocky Creek - Rate Inclusive of all fees, holiday rental in Oldsmar

Waterfront Cottage on Rocky Creek - Rate Inclusive of all fees

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Cottage on Rocky Creek, holiday rental in Oldsmar
Waterfront Cottage on Rocky Creek, holiday rental in Oldsmar
Waterfront Cottage on Rocky Creek, holiday rental in Oldsmar

Waterfront Cottage on Rocky Creek

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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, holiday rental in Oldsmar
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to BonaVista Beach House:) great for couples and families, holiday rental in Oldsmar
Welcome to BonaVista Beach House:) great for couples and families, holiday rental in Oldsmar
Welcome to BonaVista Beach House:) great for couples and families, holiday rental in Oldsmar

Welcome to BonaVista Beach House:) great for couples and families

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Resort House ☞ManCave☞ Heated Pool ☞Jacuzzi ☞ BRAND NEW HOME, holiday rental in Oldsmar
Luxury Resort House ☞ManCave☞ Heated Pool ☞Jacuzzi ☞ BRAND NEW HOME, holiday rental in Oldsmar
Luxury Resort House ☞ManCave☞ Heated Pool ☞Jacuzzi ☞ BRAND NEW HOME, holiday rental in Oldsmar

Luxury Resort House ☞ManCave☞ Heated Pool ☞Jacuzzi ☞ BRAND NEW HOME

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Suite Retreat - Upstairs (Lower Unit Prop #1272052), holiday rental in Oldsmar
Suite Retreat - Upstairs (Lower Unit Prop #1272052), holiday rental in Oldsmar
Suite Retreat - Upstairs (Lower Unit Prop #1272052), holiday rental in Oldsmar

Suite Retreat - Upstairs (Lower Unit Prop #1272052)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tampa Oasis Centrally Located to 3 Major Hospitals, holiday rental in Oldsmar
Tampa Oasis Centrally Located to 3 Major Hospitals, holiday rental in Oldsmar
Tampa Oasis Centrally Located to 3 Major Hospitals, holiday rental in Oldsmar

Tampa Oasis Centrally Located to 3 Major Hospitals

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Like Home in Tampa Fl, holiday rental in Oldsmar
Like Home in Tampa Fl, holiday rental in Oldsmar
Like Home in Tampa Fl, holiday rental in Oldsmar

Like Home in Tampa Fl

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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It's a simple modern home and family friendly, holiday rental in Oldsmar
It's a simple modern home and family friendly, holiday rental in Oldsmar
It's a simple modern home and family friendly, holiday rental in Oldsmar

It's a simple modern home and family friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Flamingo Bungalow Beautiful Tampa Retreat, holiday rental in Oldsmar
Flamingo Bungalow Beautiful Tampa Retreat, holiday rental in Oldsmar
Flamingo Bungalow Beautiful Tampa Retreat, holiday rental in Oldsmar

Flamingo Bungalow Beautiful Tampa Retreat

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Paradise Oasis-Resort House, holiday rental in Oldsmar
Paradise Oasis-Resort House, holiday rental in Oldsmar
Paradise Oasis-Resort House, holiday rental in Oldsmar

Paradise Oasis-Resort House

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Florida Blue House, holiday rental in Oldsmar
Florida Blue House, holiday rental in Oldsmar
Florida Blue House, holiday rental in Oldsmar

Florida Blue House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tampa Bay Paradise - 3 Bdr. Pool, Bay Access, 5 Miles to Beach, 24. Hour Pro-Hos, holiday rental in Oldsmar
Tampa Bay Paradise - 3 Bdr. Pool, Bay Access, 5 Miles to Beach, 24. Hour Pro-Hos, holiday rental in Oldsmar
Tampa Bay Paradise - 3 Bdr. Pool, Bay Access, 5 Miles to Beach, 24. Hour Pro-Hos, holiday rental in Oldsmar

Tampa Bay Paradise - 3 Bdr. Pool, Bay Access, 5 Miles to Beach, 24. Hour Pro-Hos

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serenity LakeHouse in Tampa, holiday rental in Oldsmar
Serenity LakeHouse in Tampa, holiday rental in Oldsmar
Serenity LakeHouse in Tampa, holiday rental in Oldsmar

Serenity LakeHouse in Tampa

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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WanderJaunt | Rocco | 1BR | Town N Country, holiday rental in Oldsmar
WanderJaunt | Rocco | 1BR | Town N Country, holiday rental in Oldsmar
WanderJaunt | Rocco | 1BR | Town N Country, holiday rental in Oldsmar

WanderJaunt | Rocco | 1BR | Town N Country

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Dolphin Bay Retreat, holiday rental in Oldsmar
Dolphin Bay Retreat, holiday rental in Oldsmar
Dolphin Bay Retreat, holiday rental in Oldsmar

Dolphin Bay Retreat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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La Rustic House, holiday rental in Oldsmar
La Rustic House, holiday rental in Oldsmar
La Rustic House, holiday rental in Oldsmar

La Rustic House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront Town-home w/Deep Water & Direct Bay access 3 Bed/2.5 Bath, holiday rental in Oldsmar
Waterfront Town-home w/Deep Water & Direct Bay access 3 Bed/2.5 Bath, holiday rental in Oldsmar
Waterfront Town-home w/Deep Water & Direct Bay access 3 Bed/2.5 Bath, holiday rental in Oldsmar

Waterfront Town-home w/Deep Water & Direct Bay access 3 Bed/2.5 Bath

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Home Tampa bay area!!!, holiday rental in Oldsmar
Cozy Home Tampa bay area!!!, holiday rental in Oldsmar
Cozy Home Tampa bay area!!!, holiday rental in Oldsmar

Cozy Home Tampa bay area!!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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La Villita, holiday rental in Oldsmar
La Villita, holiday rental in Oldsmar
La Villita, holiday rental in Oldsmar

La Villita

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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⭑ Pool-80 in TV-BBQ Grill- Beach- Airport ⭑, holiday rental in Oldsmar
⭑ Pool-80 in TV-BBQ Grill- Beach- Airport ⭑, holiday rental in Oldsmar
⭑ Pool-80 in TV-BBQ Grill- Beach- Airport ⭑, holiday rental in Oldsmar

⭑ Pool-80 in TV-BBQ Grill- Beach- Airport ⭑

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful 3 Bedroom Home || Close to Airport, holiday rental in Oldsmar
Peaceful 3 Bedroom Home || Close to Airport, holiday rental in Oldsmar
Peaceful 3 Bedroom Home || Close to Airport, holiday rental in Oldsmar

Peaceful 3 Bedroom Home || Close to Airport

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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