Vacation rentals in Caladesi Island, FL

23 available vacation rental offers

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Best vacation rentals and Airbnb offers in Caladesi Island, FL

Pink Flamingo - Caladesi Island, FL
8 ★ 2 reviews

Pink Flamingo

Holiday Home, Caladesi Island

Pink Flamingo is a holiday home in Caladesi Island, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Pink Flamingo

Pink Flamingo is a holiday home in Caladesi Island, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,425.

From$145/night
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Sunny Side Cottages - Caladesi Island, FL

Sunny Side Cottages

Apartment, Caladesi Island

Sunny Side Cottages is a apartment in Caladesi Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Sunny Side Cottages

Sunny Side Cottages is a apartment in Caladesi Island, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $937.

From$108/night
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Condo On The Beach - Heated Pool - Self Check-in - Caladesi Island, FL

Condo On The Beach - Heated Pool - Self Check-in

Apartment, Caladesi Island

Condo On The Beach - Heated Pool - Self Check-in is a apartment in Caladesi Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About Condo On The Beach - Heated Pool - Self Check-in

Condo On The Beach - Heated Pool - Self Check-in is a apartment in Caladesi Island, with 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, free wifi, beachfront, beach front, and ac.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,546.

From$180/night
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Beso del Sol Resort in Dunedin - Perfect Location & Relaxation! - Caladesi Island, FL

Beso del Sol Resort in Dunedin - Perfect Location & Relaxation!

Apartment, Caladesi Island

Beso del Sol Resort in Dunedin - Perfect Location & Relaxation! is a apartment in Caladesi Island, with pool access and a quieter setting. This stay gives travelers a comfortable base for…

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About Beso del Sol Resort in Dunedin - Perfect Location & Relaxation!

Beso del Sol Resort in Dunedin - Perfect Location & Relaxation! is a apartment in Caladesi Island, with pool 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, pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,412.

From$129/night
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Pet-friendly vacation rentals in Caladesi Island, FL

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

Belleair Beach Club 315 - Caladesi Island, FL

Belleair Beach Club 315

Holiday Home, Caladesi Island

Belleair Beach Club 315 is a holiday home in Caladesi Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About Belleair Beach Club 315

Belleair Beach Club 315 is a holiday home in Caladesi Island, 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 parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,247.

From$233/night
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4 Bedroom Clearwater Vacation Home with Amazing Backyard - Caladesi Island, FL

4 Bedroom Clearwater Vacation Home with Amazing Backyard

Holiday Home, Caladesi Island

4 Bedroom Clearwater Vacation Home with Amazing Backyard is a holiday home in Caladesi Island, with pet-friendly space, pool access, and room for a group. This stay gives travelers a…

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About 4 Bedroom Clearwater Vacation Home with Amazing Backyard

4 Bedroom Clearwater Vacation Home with Amazing Backyard is a holiday home in Caladesi Island, with pet-friendly space, pool 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $4,698.

From$453/night
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201 Belleair Beach Club - Caladesi Island, FL

201 Belleair Beach Club

Holiday Home, Caladesi Island

201 Belleair Beach Club is a holiday home in Caladesi Island, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 201 Belleair Beach Club

201 Belleair Beach Club is a holiday home in Caladesi Island, with pet-friendly space 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 wifi, pet friendly, pets friendly, beachfront, and beach front.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,501.

From$150/night
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Vacation rentals with a pool in Caladesi Island, FL

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

Modern 4 bedroom House with swimming pool - Caladesi Island, FL

Modern 4 bedroom House with swimming pool

Holiday Home, Caladesi Island

Modern 4 bedroom House with swimming pool is a holiday home in Caladesi Island, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Modern 4 bedroom House with swimming pool

Modern 4 bedroom House with swimming pool is a holiday home in Caladesi Island, with pool access, parking, 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, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,216.

From$255/night
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Sunset Beach House - Caladesi Island, FL

Sunset Beach House

Holiday Home, Caladesi Island

Sunset Beach House is a holiday home in Caladesi Island, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sunset Beach House

Sunset Beach House is a holiday home in Caladesi Island, 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: free cancellation, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,276.

From$374/night
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Aldea A8 Beachfront 2 Bedroom 2 Bath - Tranquil Belleair Beach - Caladesi Island, FL

Aldea A8 Beachfront 2 Bedroom 2 Bath - Tranquil Belleair Beach

Apartment, Caladesi Island

Aldea A8 Beachfront 2 Bedroom 2 Bath - Tranquil Belleair Beach is a apartment in Caladesi Island, with pool access, easy beach access, and parking. This stay gives travelers a comfortable…

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About Aldea A8 Beachfront 2 Bedroom 2 Bath - Tranquil Belleair Beach

Aldea A8 Beachfront 2 Bedroom 2 Bath - Tranquil Belleair Beach is a apartment in Caladesi Island, 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, parking, paid parking, and heated pool.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,912.

From$208/night
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Pool & Patio Access: Breezy Getaway in Palm Harbor - Caladesi Island, FL

Pool & Patio Access: Breezy Getaway in Palm Harbor

Apartment, Caladesi Island

Pool & Patio Access: Breezy Getaway in Palm Harbor is a apartment in Caladesi Island, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Pool & Patio Access: Breezy Getaway in Palm Harbor

Pool & Patio Access: Breezy Getaway in Palm Harbor is a apartment in Caladesi Island, with pool access, outdoor 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, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,272.

From$261/night
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