Vacation rentals in Webster, FL

Best Vacation rentals and Airbnb offers in Webster, FL

Cozy Retreat Near Sawgrass Market & Brownwood Paddock Square!

Holiday Home, Webster

Cozy Retreat Near Sawgrass Market & Brownwood Paddock Square! is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable…

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About Cozy Retreat Near Sawgrass Market & Brownwood Paddock Square!

Cozy Retreat Near Sawgrass Market & Brownwood Paddock Square! is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $978.

From$70/night

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Stylish Shadybrook retreat with golf cart, bikes & Tesla charger!

Holiday Home, Webster

Stylish Shadybrook retreat with golf cart, bikes & Tesla charger! is a holiday home in Webster, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Stylish Shadybrook retreat with golf cart, bikes & Tesla charger!

Stylish Shadybrook retreat with golf cart, bikes & Tesla charger! is a holiday home in Webster, 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: pool, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $978.

From$70/night

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Cheryl’s Happy Place at Villages of Shady Brook

Holiday Home, Webster

Cheryl’s Happy Place at Villages of Shady Brook is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Cheryl’s Happy Place at Villages of Shady Brook

Cheryl’s Happy Place at Villages of Shady Brook is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $928.

From$75/night

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Charming home w/spacious kitchen, water view, enclosed lanai, & Pet Friendly

Holiday Home, Webster

Charming home w/spacious kitchen, water view, enclosed lanai, & Pet Friendly is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Charming home w/spacious kitchen, water view, enclosed lanai, & Pet Friendly

Charming home w/spacious kitchen, water view, enclosed lanai, & Pet Friendly is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,042.

From$75/night

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Browse Vacation Rentals with a Pool in Webster, FL

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

Your Perfect Home in The Village of Citrus Grove!

Holiday Home, Webster

Your Perfect Home in The Village of Citrus Grove! is a holiday home in Webster, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Your Perfect Home in The Village of Citrus Grove!

Your Perfect Home in The Village of Citrus Grove! is a holiday home in Webster, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,203.

From$94/night

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Brand New 3-Bed, 2-Bath Home in The Villages – Your Dream Home Awaits!

Holiday Home, Webster

Brand New 3-Bed, 2-Bath Home in The Villages – Your Dream Home Awaits! is a holiday home in Webster, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Brand New 3-Bed, 2-Bath Home in The Villages – Your Dream Home Awaits!

Brand New 3-Bed, 2-Bath Home in The Villages – Your Dream Home Awaits! is a holiday home in Webster, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,231.

From$100/night

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Chic, comfy, and ready for Villages adventures—golf cart included!

Holiday Home, Webster

Chic, comfy, and ready for Villages adventures—golf cart included! is a holiday home in Webster, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Chic, comfy, and ready for Villages adventures—golf cart included!

Chic, comfy, and ready for Villages adventures—golf cart included! is a holiday home in Webster, 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: pool, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,247.

From$100/night

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Eastport Footprint - The Villages 2/2 + Workout Room and Golf Cart in The Village of Moultrie Creek

Holiday Home, Webster

Eastport Footprint - The Villages 2/2 + Workout Room and Golf Cart in The Village of Moultrie Creek is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access.…

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About Eastport Footprint - The Villages 2/2 + Workout Room and Golf Cart in The Village of Moultrie Creek

Eastport Footprint - The Villages 2/2 + Workout Room and Golf Cart in The Village of Moultrie Creek is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,415.

From$111/night

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Best Webster, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages

Villa, Webster

New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages is a villa in Webster, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages

New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages is a villa in Webster, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $977.

From$93/night

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Great 3/2 Villages Home with Amenities Access

Villa, Webster

Great 3/2 Villages Home with Amenities Access is a villa in Webster, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Great 3/2 Villages Home with Amenities Access

Great 3/2 Villages Home with Amenities Access is a villa in Webster, 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 $1,065.

From$97/night

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Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport

Holiday Home, Webster

Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport is a holiday home in Webster, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport

Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport is a holiday home in Webster, 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 $1,062.

From$100/night

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Large 3 bedroom with Golf Cart!

Holiday Home, Webster

Large 3 bedroom with Golf Cart! is a holiday home in Webster, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Large 3 bedroom with Golf Cart!

Large 3 bedroom with Golf Cart! is a holiday home in Webster, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,045.

From$103/night

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Best Pet-Friendly Vacation Rentals in Webster, FL

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

Duck Haven - Wildlife Sanctuary - 5 miles to I75

Apartment, Webster

Duck Haven - Wildlife Sanctuary - 5 miles to I75 is a apartment in Webster, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Duck Haven - Wildlife Sanctuary - 5 miles to I75

Duck Haven - Wildlife Sanctuary - 5 miles to I75 is a apartment in Webster, 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 $818.

From$88/night

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Next/Pitch & Putt, short ride/Sawgrass, 55m/Disney

Villa, Webster

Next/Pitch & Putt, short ride/Sawgrass, 55m/Disney is a villa in Webster, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Next/Pitch & Putt, short ride/Sawgrass, 55m/Disney

Next/Pitch & Putt, short ride/Sawgrass, 55m/Disney is a villa in Webster, 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 $1,192.

From$88/night

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Timothy’s Lanai Oasis at WellPoint – Corner Villa

Holiday Home, Webster

Timothy’s Lanai Oasis at WellPoint – Corner Villa is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Timothy’s Lanai Oasis at WellPoint – Corner Villa

Timothy’s Lanai Oasis at WellPoint – Corner Villa is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,063.

From$88/night

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The McLucas Getaway (Lake Denham)

Holiday Home, Webster

The McLucas Getaway (Lake Denham) is a holiday home in Webster, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The McLucas Getaway (Lake Denham)

The McLucas Getaway (Lake Denham) is a holiday home in Webster, 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 $1,144.

From$94/night

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Best Webster, FL vacation rentals with a kitchen

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

Logan’s Fun Villages Villa

Holiday Home, Webster

Logan’s Fun Villages Villa is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Logan’s Fun Villages Villa

Logan’s Fun Villages Villa is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,110.

From$94/night

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The Villages, Home away from Home with great amenities.

Holiday Home, Webster

The Villages, Home away from Home with great amenities. is a holiday home in Webster, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About The Villages, Home away from Home with great amenities.

The Villages, Home away from Home with great amenities. is a holiday home in Webster, 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 $928.

From$95/night

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Newly built 3 bedroom with Golf Cart!

Holiday Home, Webster

Newly built 3 bedroom with Golf Cart! is a holiday home in Webster, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Newly built 3 bedroom with Golf Cart!

Newly built 3 bedroom with Golf Cart! is a holiday home in Webster, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,056.

From$105/night

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Welcome to our Shady Brook Retreat!

Holiday Home, Webster

Welcome to our Shady Brook Retreat! is a holiday home in Webster, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Welcome to our Shady Brook Retreat!

Welcome to our Shady Brook Retreat! is a holiday home in Webster, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,131.

From$107/night

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Our Favorite Family-Friendly Vacation Rentals in Webster, FL

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

Cozy Cowboy Cottage at Spotted Dance Ranch

Cabin, Webster

Cozy Cowboy Cottage at Spotted Dance Ranch is a cabin in Webster, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Cowboy Cottage at Spotted Dance Ranch

Cozy Cowboy Cottage at Spotted Dance Ranch is a cabin in Webster, 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 $873.

From$87/night

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Rachel’s Coastal Fun Cottage at The Villages

Holiday Home, Webster

Rachel’s Coastal Fun Cottage at The Villages is a holiday home in Webster, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Rachel’s Coastal Fun Cottage at The Villages

Rachel’s Coastal Fun Cottage at The Villages is a holiday home in Webster, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,110.

From$94/night

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The Blue Door Cottage at The Villages

Holiday Home, Webster

The Blue Door Cottage at The Villages is a holiday home in Webster, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Blue Door Cottage at The Villages

The Blue Door Cottage at The Villages is a holiday home in Webster, 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,103.

From$95/night

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561d Large 3 Bedroom With Golf Cart!

Cottage, Webster

561d Large 3 Bedroom With Golf Cart! is a cottage in Webster, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 561d Large 3 Bedroom With Golf Cart!

561d Large 3 Bedroom With Golf Cart! is a cottage in Webster, 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: kitchen, with kitchen, parking, free parking, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,428.

From$138/night

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