Vacation rentals in Cherry Estates, FL

Best Vacation rentals and Airbnb offers in Cherry Estates, FL

Adorable Waterfront Condo, Boat Slip and Pool!

Condo, Cherry Estates

Adorable Waterfront Condo, Boat Slip and Pool! is a condo in Cherry Estates, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Adorable Waterfront Condo, Boat Slip and Pool!

Adorable Waterfront Condo, Boat Slip and Pool! is a condo in Cherry Estates, 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 $1,078.

From$100/night

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Waterfront Effeciency Apartment

Apartment, Cherry Estates

Waterfront Effeciency Apartment is a apartment in Cherry Estates, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Waterfront Effeciency Apartment

Waterfront Effeciency Apartment is a apartment in Cherry Estates, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

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

From$105/night

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Waterfront Paradise - 2BR/2BA Home with Gulf Access in Pine Island, FL

Holiday Home, Cherry Estates

Waterfront Paradise - 2BR/2BA Home with Gulf Access in Pine Island, FL is a holiday home in Cherry Estates, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Waterfront Paradise - 2BR/2BA Home with Gulf Access in Pine Island, FL

Waterfront Paradise - 2BR/2BA Home with Gulf Access in Pine Island, FL is a holiday home in Cherry Estates, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,176.

From$108/night

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Boat Dock & Patio: Canal-Front St James City Home!

Holiday Home, Cherry Estates

Boat Dock & Patio: Canal-Front St James City Home! is a holiday home in Cherry Estates, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Boat Dock & Patio: Canal-Front St James City Home!

Boat Dock & Patio: Canal-Front St James City Home! is a holiday home in Cherry Estates, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,362.

From$110/night

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Browse Vacation Rentals with a Pool in Cherry Estates, FL

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

Waterfront 2BR/2BA Retreat with Pool, Outdoor Bar & Boat Lift – St. James City, FL

Holiday Home, Cherry Estates

Waterfront 2BR/2BA Retreat with Pool, Outdoor Bar & Boat Lift – St. James City, FL is a holiday home in Cherry Estates, with pool access, easy beach access, and parking. This stay gives…

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About Waterfront 2BR/2BA Retreat with Pool, Outdoor Bar & Boat Lift – St. James City, FL

Waterfront 2BR/2BA Retreat with Pool, Outdoor Bar & Boat Lift – St. James City, FL is a holiday home in Cherry Estates, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,691.

From$157/night

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🔆🏝LITTLE PARADISE🏝🔆

Holiday Home, Cherry Estates

🔆🏝LITTLE PARADISE🏝🔆 is a holiday home in Cherry Estates, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About 🔆🏝LITTLE PARADISE🏝🔆

🔆🏝LITTLE PARADISE🏝🔆 is a holiday home in Cherry Estates, 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,603.

From$159/night

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The Monroe Lookout! 2/2 Pool Waterfront Home!

Holiday Home, Cherry Estates

The Monroe Lookout! 2/2 Pool Waterfront Home! is a holiday home in Cherry Estates, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About The Monroe Lookout! 2/2 Pool Waterfront Home!

The Monroe Lookout! 2/2 Pool Waterfront Home! is a holiday home in Cherry Estates, 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 $1,989.

From$177/night

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Beautiful Waterfront Ideal for fishing and boating!!

Holiday Home, Cherry Estates

Beautiful Waterfront Ideal for fishing and boating!! is a holiday home in Cherry Estates, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Beautiful Waterfront Ideal for fishing and boating!!

Beautiful Waterfront Ideal for fishing and boating!! is a holiday home in Cherry Estates, with pet-friendly space, 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: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,842.

From$183/night

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Best Cherry Estates, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

West End Paradise Sanddollar 7 - Quaint Hotel Style Room near the Beach

Condo, Cherry Estates

West End Paradise Sanddollar 7 - Quaint Hotel Style Room near the Beach is a condo in Cherry Estates, with easy beach access and parking. This stay gives travelers a comfortable base for…

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About West End Paradise Sanddollar 7 - Quaint Hotel Style Room near the Beach

West End Paradise Sanddollar 7 - Quaint Hotel Style Room near the Beach is a condo in Cherry Estates, with 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, free wifi, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $797.

From$57/night

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Island Getaway, with boat ramp access nearby. You can park your boat on property

Holiday Home, Cherry Estates

Island Getaway, with boat ramp access nearby. You can park your boat on property is a holiday home in Cherry Estates, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Island Getaway, with boat ramp access nearby. You can park your boat on property

Island Getaway, with boat ramp access nearby. You can park your boat on property is a holiday home in Cherry Estates, 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 $1,183.

From$113/night

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3752 San Carlos Drive (Dockside Dreams): 3 BR, 2 BA House in Saint James City, Sleeps 7

Holiday Home, Cherry Estates

3752 San Carlos Drive (Dockside Dreams): 3 BR, 2 BA House in Saint James City, Sleeps 7 is a holiday home in Cherry Estates, with parking, kitchen access, and room for a group. This stay…

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About 3752 San Carlos Drive (Dockside Dreams): 3 BR, 2 BA House in Saint James City, Sleeps 7

3752 San Carlos Drive (Dockside Dreams): 3 BR, 2 BA House in Saint James City, Sleeps 7 is a holiday home in Cherry Estates, 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 $1,631.

From$151/night

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Gulf Access Home | Private Dock | Tarpon Fishing

Holiday Home, Cherry Estates

Gulf Access Home · Private Dock · Tarpon Fishing is a holiday home in Cherry Estates, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Gulf Access Home | Private Dock | Tarpon Fishing

Gulf Access Home · Private Dock · Tarpon Fishing is a holiday home in Cherry Estates, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,537.

From$153/night

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Best Pet-Friendly Vacation Rentals in Cherry Estates, FL

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

St. James City Vacation Home with Private Dock, Pool and Gulf Access

Holiday Home, Cherry Estates

St. James City Vacation Home with Private Dock, Pool and Gulf Access is a holiday home in Cherry Estates, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About St. James City Vacation Home with Private Dock, Pool and Gulf Access

St. James City Vacation Home with Private Dock, Pool and Gulf Access is a holiday home in Cherry Estates, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,095.

From$132/night

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Island Sunset Retreat with Jacuzzi

Holiday Home, Cherry Estates

Island Sunset Retreat with Jacuzzi is a holiday home in Cherry Estates, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Island Sunset Retreat with Jacuzzi

Island Sunset Retreat with Jacuzzi is a holiday home in Cherry Estates, with pet-friendly space 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,532.

From$150/night

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Dog-friendly, canal-front getaway with a dock, screened lanai, & washer/dryer

Holiday Home, Cherry Estates

Dog-friendly, canal-front getaway with a dock, screened lanai, & washer/dryer is a holiday home in Cherry Estates, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Dog-friendly, canal-front getaway with a dock, screened lanai, & washer/dryer

Dog-friendly, canal-front getaway with a dock, screened lanai, & washer/dryer is a holiday home in Cherry Estates, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,110.

From$153/night

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☀️TRANQUILITY VILLA☀️

Holiday Home, Cherry Estates

☀️TRANQUILITY VILLA☀️ is a holiday home in Cherry Estates, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About ☀️TRANQUILITY VILLA☀️

☀️TRANQUILITY VILLA☀️ is a holiday home in Cherry Estates, 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, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,703.

From$171/night

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Best Cherry Estates, FL vacation rentals with a kitchen

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

Skipper Lane on Salt Water Canal, Easy Gulf access

Holiday Home, Cherry Estates

Skipper Lane on Salt Water Canal, Easy Gulf access is a holiday home in Cherry Estates, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Skipper Lane on Salt Water Canal, Easy Gulf access

Skipper Lane on Salt Water Canal, Easy Gulf access is a holiday home in Cherry Estates, with 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: kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,555.

From$160/night

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Studio on the Water. Great for monthly stays!

Apartment, Cherry Estates

Studio on the Water. Great for monthly stays! is a apartment in Cherry Estates, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Studio on the Water. Great for monthly stays!

Studio on the Water. Great for monthly stays! is a apartment in Cherry Estates, 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 $1,646.

From$177/night

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Closest Inn to Deep Water in St James City. Perfect for monthly rental!

Apartment, Cherry Estates

Closest Inn to Deep Water in St James City. Perfect for monthly rental! is a apartment in Cherry Estates, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Closest Inn to Deep Water in St James City. Perfect for monthly rental!

Closest Inn to Deep Water in St James City. Perfect for monthly rental! is a apartment in Cherry Estates, 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 $1,608.

From$178/night

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Charming Seascape Casita, Kayaks and Bikes. Saint James City

Holiday Home, Cherry Estates

Charming Seascape Casita, Kayaks and Bikes. Saint James City is a holiday home in Cherry Estates, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Charming Seascape Casita, Kayaks and Bikes. Saint James City

Charming Seascape Casita, Kayaks and Bikes. Saint James City is a holiday home in Cherry Estates, 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 $1,732.

From$179/night

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Our Favorite Family-Friendly Vacation Rentals in Cherry Estates, FL

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

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

Cottage, Cherry Estates

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops! is a cottage in Cherry Estates, with easy beach access and parking. This stay gives travelers a comfortable…

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About Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops! is a cottage in Cherry Estates, with 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 wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,493.

From$149/night

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Canalfront St James City Home w/ Unique View

Cottage, Cherry Estates

Canalfront St James City Home w/ Unique View is a cottage in Cherry Estates, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Canalfront St James City Home w/ Unique View

Canalfront St James City Home w/ Unique View is a cottage in Cherry Estates, 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 $1,375.

From$150/night

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NEW Waterfront Cottage Retreat in St. James City — Brand New 1BR/1BA with Private Dock & Boat Lift

Holiday Home, Cherry Estates

NEW Waterfront Cottage Retreat in St. James City — Brand New 1BR/1BA with Private Dock & Boat Lift is a holiday home in Cherry Estates, with easy beach access, kitchen access, and room for…

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About NEW Waterfront Cottage Retreat in St. James City — Brand New 1BR/1BA with Private Dock & Boat Lift

NEW Waterfront Cottage Retreat in St. James City — Brand New 1BR/1BA with Private Dock & Boat Lift is a holiday home in Cherry Estates, with easy beach access, 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 wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,654.

From$164/night

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Sunset Views 2/3-BR w Den single family home w boat docking inl St. James City

Holiday Home, Cherry Estates

Sunset Views 2/3-BR w Den single family home w boat docking inl St. James City is a holiday home in Cherry Estates, with parking, kitchen access, and room for a group. This stay gives…

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About Sunset Views 2/3-BR w Den single family home w boat docking inl St. James City

Sunset Views 2/3-BR w Den single family home w boat docking inl St. James City is a holiday home in Cherry Estates, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,798.

From$180/night

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