Vacation rentals in Osteen, FL

Best vacation rentals and Airbnb offers in Osteen, FL

Lovely 1-bedroom apartment with AC in charming Osteen

Apartment, Osteen

Lovely 1-bedroom apartment with AC in charming Osteen is a apartment in Osteen, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lovely 1-bedroom apartment with AC in charming Osteen

Lovely 1-bedroom apartment with AC in charming Osteen is a apartment in Osteen, 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 $559.

From$80/night

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Bella Breeze

Apartment, Osteen

Bella Breeze is a apartment in Osteen, with parking and 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 Bella Breeze

Bella Breeze is a apartment in Osteen, 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $720.

From$83/night

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Sandford Vacation Rental Near Airport & Lake!

Holiday Home, Osteen

Sandford Vacation Rental Near Airport & Lake! is a holiday home in Osteen, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Sandford Vacation Rental Near Airport & Lake!

Sandford Vacation Rental Near Airport & Lake! is a holiday home in Osteen, 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 heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,230.

From$92/night

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Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford

Apartment, Osteen

Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford is a apartment in Osteen, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford

Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford is a apartment in Osteen, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $652.

From$93/night

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Vacation rentals with a pool in Osteen, FL

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

The Lion's Den, Studio guest house.

Apartment, Osteen

The Lion's Den, Studio guest house. is a apartment in Osteen, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Lion's Den, Studio guest house.

The Lion's Den, Studio guest house. is a apartment in Osteen, 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 $789.

From$113/night

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Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House

Guest House, Osteen

Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House is a guest house in Osteen, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House

Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House is a guest house in Osteen, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $861.

From$123/night

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COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

Apartment, Osteen

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community is a apartment in Osteen, with pool access, easy beach access, and parking. This stay gives travelers a…

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About COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community is a apartment in Osteen, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,080.

From$154/night

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Condo w/ Pool & Beach Access Near Theme Park

Condo, Osteen

Condo w/ Pool & Beach Access Near Theme Park is a condo in Osteen, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Condo w/ Pool & Beach Access Near Theme Park

Condo w/ Pool & Beach Access Near Theme Park is a condo in Osteen, with pool access, easy beach 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,123.

From$160/night

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Vacation rentals with parking in Osteen, FL

Find vacation rentals that make arriving by car easier.

Orlando Oasis

Holiday Home, Osteen

Orlando Oasis is a holiday home in Osteen, 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 Orlando Oasis

Orlando Oasis is a holiday home in Osteen, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $680.

From$97/night

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Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Apartment, Osteen

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex is a apartment in Osteen, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex is a apartment in Osteen, 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 $691.

From$99/night

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City Guesthouse in beautiful Historic Downtown Sanford

Guest House, Osteen

City Guesthouse in beautiful Historic Downtown Sanford is a guest house in Osteen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford is a guest house in Osteen, 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 $954.

From$136/night

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River City Retreat

Holiday Home, Osteen

River City Retreat is a holiday home in Osteen, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About River City Retreat

River City Retreat is a holiday home in Osteen, with parking 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, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $963.

From$138/night

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Pet-friendly vacation rentals in Osteen, FL

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

Serenity @ Court

Apartment, Osteen

Serenity @ Court is a apartment in Osteen, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Serenity @ Court

Serenity @ Court is a apartment in Osteen, with pet-friendly 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 cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $911.

From$130/night

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FL LAKEFRONT full house 2/1

Holiday Home, Osteen

FL LAKEFRONT full house 2/1 is a holiday home in Osteen, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About FL LAKEFRONT full house 2/1

FL LAKEFRONT full house 2/1 is a holiday home in Osteen, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $922.

From$132/night

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Downtown Duplex A Amazing Location

Apartment, Osteen

Downtown Duplex A Amazing Location is a apartment in Osteen, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Downtown Duplex A Amazing Location

Downtown Duplex A Amazing Location is a apartment in Osteen, 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 $983.

From$140/night

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The Velvet Leaf - fenced yard

Holiday Home, Osteen

The Velvet Leaf - fenced yard is a holiday home in Osteen, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Velvet Leaf - fenced yard

The Velvet Leaf - fenced yard is a holiday home in Osteen, with pet-friendly 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 cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,047.

From$150/night

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Vacation rentals with a kitchen in Osteen, FL

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

Home Sweet Home

Holiday Home, Osteen

Home Sweet Home is a holiday home in Osteen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Home Sweet Home

Home Sweet Home is a holiday home in Osteen, 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 $1,062.

From$152/night

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Charming 2-bedroom apartment in lovely DeBary with AC, WiFi

Apartment, Osteen

Charming 2-bedroom apartment in lovely DeBary with AC, WiFi is a apartment in Osteen, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 2-bedroom apartment in lovely DeBary with AC, WiFi

Charming 2-bedroom apartment in lovely DeBary with AC, WiFi is a apartment in Osteen, with 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,068.

From$153/night

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The Shed

Holiday Home, Osteen

The Shed is a holiday home in Osteen, with parking and 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 The Shed

The Shed is a holiday home in Osteen, 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 $1,070.

From$153/night

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The Cozy Euphoric cottage nestled in nature with relaxing River front views.

Cottage, Osteen

The Cozy Euphoric cottage nestled in nature with relaxing River front views. is a cottage in Osteen, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About The Cozy Euphoric cottage nestled in nature with relaxing River front views.

The Cozy Euphoric cottage nestled in nature with relaxing River front views. is a cottage in Osteen, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,275.

From$182/night

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Family-friendly vacation rentals in Osteen, FL

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

Sandford Vacation Rental Near Airport & Lake!

Cottage, Osteen

Sandford Vacation Rental Near Airport & Lake! is a cottage in Osteen, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sandford Vacation Rental Near Airport & Lake!

Sandford Vacation Rental Near Airport & Lake! is a cottage in Osteen, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,274.

From$123/night

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2BR COTTAGE IN SANFORD HISTORIC DISTRICT

Cottage, Osteen

2BR COTTAGE IN SANFORD HISTORIC DISTRICT is a cottage in Osteen, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2BR COTTAGE IN SANFORD HISTORIC DISTRICT

2BR COTTAGE IN SANFORD HISTORIC DISTRICT is a cottage in Osteen, with 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $992.

From$142/night

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Relaxing 2-bedroom cottage in beautiful Sanford

Cottage, Osteen

Relaxing 2-bedroom cottage in beautiful Sanford is a cottage in Osteen, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Relaxing 2-bedroom cottage in beautiful Sanford

Relaxing 2-bedroom cottage in beautiful Sanford is a cottage in Osteen, 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 $1,025.

From$146/night

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Quiet Lakeside home BBQ, RELAX, FISH AND REPEAT

Holiday Home, Osteen

Quiet Lakeside home BBQ, RELAX, FISH AND REPEAT is a holiday home in Osteen, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Quiet Lakeside home BBQ, RELAX, FISH AND REPEAT

Quiet Lakeside home BBQ, RELAX, FISH AND REPEAT is a holiday home in Osteen, with 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,253.

From$179/night

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