Vacation rentals in Pine Island Sound, FL

Best Vacation rentals and Airbnb offers in Pine Island Sound, FL

Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.

Holiday Home, Pine Island Sound

Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping. is a holiday home in Pine Island Sound, with pool access, parking, and kitchen access. This stay gives…

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About Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.

Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping. is a holiday home in Pine Island Sound, 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 $1,195.

From$118/night

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Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access

Holiday Home, Pine Island Sound

Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access is a holiday home in Pine Island Sound, with pet-friendly space, pool access, and easy beach access. This…

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About Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access

Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access is a holiday home in Pine Island Sound, 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,238.

From$120/night

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ISLAND TIME! DOCK! POOL! KAYAKS! BOAT To BEACH! PETS ALLOWED!

Holiday Home, Pine Island Sound

ISLAND TIME! DOCK! POOL! KAYAKS! BOAT To BEACH! PETS ALLOWED! is a holiday home in Pine Island Sound, with pet-friendly space, pool access, and easy beach access. This stay gives travelers…

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About ISLAND TIME! DOCK! POOL! KAYAKS! BOAT To BEACH! PETS ALLOWED!

ISLAND TIME! DOCK! POOL! KAYAKS! BOAT To BEACH! PETS ALLOWED! is a holiday home in Pine Island Sound, 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,261.

From$123/night

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Boaters/fishing paradise. Friendly people all over

Holiday Home, Pine Island Sound

Boaters/fishing paradise. Friendly people all over is a holiday home in Pine Island Sound, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Boaters/fishing paradise. Friendly people all over

Boaters/fishing paradise. Friendly people all over is a holiday home in Pine Island Sound, 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 $1,270.

From$126/night

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Browse Waterfront Vacation Rentals in Pine Island Sound, FL

Discover vacation rentals close to the coast, water, and beach areas around Pine Island Sound, FL.

Salt Shack-Waterfront townhome with dockage on charming North Captiva Island

Holiday Home, Pine Island Sound

Salt Shack-Waterfront townhome with dockage on charming North Captiva Island is a holiday home in Pine Island Sound, with pool access, easy beach access, and kitchen access. This stay gives…

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About Salt Shack-Waterfront townhome with dockage on charming North Captiva Island

Salt Shack-Waterfront townhome with dockage on charming North Captiva Island is a holiday home in Pine Island Sound, 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 $2,819.

From$285/night

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Coconut Castaway | Ocean Views, Golf Cart & Club Pool

Holiday Home, Pine Island Sound

Coconut Castaway · Ocean Views, Golf Cart & Club Pool is a holiday home in Pine Island Sound, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Coconut Castaway | Ocean Views, Golf Cart & Club Pool

Coconut Castaway · Ocean Views, Golf Cart & Club Pool is a holiday home in Pine Island Sound, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,914.

From$287/night

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2BR North Captiva Cottage with Golf Cart Steps from the Beach

Guest House, Pine Island Sound

2BR North Captiva Cottage with Golf Cart Steps from the Beach is a guest house in Pine Island Sound, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About 2BR North Captiva Cottage with Golf Cart Steps from the Beach

2BR North Captiva Cottage with Golf Cart Steps from the Beach is a guest house in Pine Island Sound, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,098.

From$289/night

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SPECTACULAR HARBOR VIEWS! WATERFRONT PROPERTY WITH DOCK

Holiday Home, Pine Island Sound

SPECTACULAR HARBOR VIEWS! WATERFRONT PROPERTY WITH DOCK is a holiday home in Pine Island Sound, with pool access, easy beach access, and parking. This stay gives travelers a comfortable…

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About SPECTACULAR HARBOR VIEWS! WATERFRONT PROPERTY WITH DOCK

SPECTACULAR HARBOR VIEWS! WATERFRONT PROPERTY WITH DOCK is a holiday home in Pine Island Sound, 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 $3,088.

From$292/night

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Browse Vacation Rentals with a Pool in Pine Island Sound, FL

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

Gorgeous Marina Villas Residence at South Seas

Condo, Pine Island Sound

Gorgeous Marina Villas Residence at South Seas is a condo in Pine Island Sound, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Gorgeous Marina Villas Residence at South Seas

Gorgeous Marina Villas Residence at South Seas is a condo in Pine Island Sound, 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 $2,147.

From$224/night

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Modern 2BR Retreat in Sunset Captiva – Steps to Beach & Village w/ King Bed

Holiday Home, Pine Island Sound

Modern 2BR Retreat in Sunset Captiva – Steps to Beach & Village w/ King Bed is a holiday home in Pine Island Sound, with pool access, easy beach access, and kitchen access. This stay gives…

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About Modern 2BR Retreat in Sunset Captiva – Steps to Beach & Village w/ King Bed

Modern 2BR Retreat in Sunset Captiva – Steps to Beach & Village w/ King Bed is a holiday home in Pine Island Sound, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,919.

From$264/night

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Modern Renovation~2 Club Pools SHC&ICNC 👙 Kayaks 🛶 Bikes 🚲, Golf Cart 🚙 Dock

Holiday Home, Pine Island Sound

Modern Renovation~2 Club Pools SHC&ICNC 👙 Kayaks 🛶 Bikes 🚲, Golf Cart 🚙 Dock is a holiday home in Pine Island Sound, with pool access and kitchen access. This stay gives travelers a…

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About Modern Renovation~2 Club Pools SHC&ICNC 👙 Kayaks 🛶 Bikes 🚲, Golf Cart 🚙 Dock

Modern Renovation~2 Club Pools SHC&ICNC 👙 Kayaks 🛶 Bikes 🚲, Golf Cart 🚙 Dock is a holiday home in Pine Island Sound, 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 $2,870.

From$269/night

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Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk…

Holiday Home, Pine Island Sound

Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk… is a holiday home in Pine Island Sound, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk…

Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk… is a holiday home in Pine Island Sound, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,662.

From$269/night

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Best Pine Island Sound, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Spacious 2-bedroom upstairs unit in a house surrounded by nature in Pine island

Holiday Home, Pine Island Sound

Spacious 2-bedroom upstairs unit in a house surrounded by nature in Pine island is a holiday home in Pine Island Sound, with pet-friendly space, parking, and room for a group. This stay…

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About Spacious 2-bedroom upstairs unit in a house surrounded by nature in Pine island

Spacious 2-bedroom upstairs unit in a house surrounded by nature in Pine island is a holiday home in Pine Island Sound, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,906.

From$201/night

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Discover Tranquility at Lands End Condo

Condo, Pine Island Sound

Discover Tranquility at Lands End Condo is a condo in Pine Island Sound, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Discover Tranquility at Lands End Condo

Discover Tranquility at Lands End Condo is a condo in Pine Island Sound, 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,825.

From$258/night

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LaySea 8 - Across from Nature Preserve and steps to the best beach!

Holiday Home, Pine Island Sound

LaySea 8 - Across from Nature Preserve and steps to the best beach! is a holiday home in Pine Island Sound, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About LaySea 8 - Across from Nature Preserve and steps to the best beach!

LaySea 8 - Across from Nature Preserve and steps to the best beach! is a holiday home in Pine Island Sound, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,978.

From$293/night

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Romantic beach home with golf cart Remodeled Coastal charm

Cottage, Pine Island Sound

Romantic beach home with golf cart Remodeled Coastal charm is a cottage in Pine Island Sound, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Romantic beach home with golf cart Remodeled Coastal charm

Romantic beach home with golf cart Remodeled Coastal charm is a cottage in Pine Island Sound, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,434.

From$356/night

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Best Pet-Friendly Vacation Rentals in Pine Island Sound, FL

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

The Crab Shack - Cozy Comfort in Flamingo Bay - 2Bed/1Bath

Holiday Home, Pine Island Sound

The Crab Shack - Cozy Comfort in Flamingo Bay - 2Bed/1Bath is a holiday home in Pine Island Sound, with pet-friendly space, easy beach access, and parking. This stay gives travelers a…

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About The Crab Shack - Cozy Comfort in Flamingo Bay - 2Bed/1Bath

The Crab Shack - Cozy Comfort in Flamingo Bay - 2Bed/1Bath is a holiday home in Pine Island Sound, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,323.

From$128/night

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The Golden Flamingo – 2B/1Ba – Pool & Boat Ramp in Flamingo Bay

Holiday Home, Pine Island Sound

The Golden Flamingo – 2B/1Ba – Pool & Boat Ramp in Flamingo Bay is a holiday home in Pine Island Sound, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About The Golden Flamingo – 2B/1Ba – Pool & Boat Ramp in Flamingo Bay

The Golden Flamingo – 2B/1Ba – Pool & Boat Ramp in Flamingo Bay is a holiday home in Pine Island Sound, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,416.

From$140/night

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Charming 3-bedroom upstairs unit in a house with a shared pool in pine island

Holiday Home, Pine Island Sound

Charming 3-bedroom upstairs unit in a house with a shared pool in pine island is a holiday home in Pine Island Sound, with pet-friendly space, pool access, and room for a group. This stay…

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About Charming 3-bedroom upstairs unit in a house with a shared pool in pine island

Charming 3-bedroom upstairs unit in a house with a shared pool in pine island is a holiday home in Pine Island Sound, 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: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,795.

From$187/night

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BEACH DAYZ - LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES!

Holiday Home, Pine Island Sound

BEACH DAYZ - LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES! is a holiday home in Pine Island Sound, with pet-friendly space, pool access, and easy beach access. This…

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About BEACH DAYZ - LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES!

BEACH DAYZ - LUXE TRUE OCEAN BEACH FRONT! AMAZING VIEWS + ISLAND CLUB AMENITIES! is a holiday home in Pine Island Sound, 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: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,173.

From$300/night

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Best Pine Island Sound, FL vacation rentals with a kitchen

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

Beautiful 3bedroom second floor with full kitchen, a pool in pine island

Holiday Home, Pine Island Sound

Beautiful 3bedroom second floor with full kitchen, a pool in pine island is a holiday home in Pine Island Sound, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Beautiful 3bedroom second floor with full kitchen, a pool in pine island

Beautiful 3bedroom second floor with full kitchen, a pool in pine island is a holiday home in Pine Island Sound, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,273.

From$239/night

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Casita Salida del Sol-North Captiva Island Waterfront townhouse w/dockage

Holiday Home, Pine Island Sound

Casita Salida del Sol-North Captiva Island Waterfront townhouse w/dockage is a holiday home in Pine Island Sound, with pool access, easy beach access, and kitchen access. This stay gives…

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About Casita Salida del Sol-North Captiva Island Waterfront townhouse w/dockage

Casita Salida del Sol-North Captiva Island Waterfront townhouse w/dockage is a holiday home in Pine Island Sound, 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 $3,054.

From$295/night

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TARPON COVE - Coastal island home on a private island. New outdoor deck/fire pit

Holiday Home, Pine Island Sound

TARPON COVE - Coastal island home on a private island. New outdoor deck/fire pit is a holiday home in Pine Island Sound, with pool access, outdoor space, and kitchen access. This stay gives…

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About TARPON COVE - Coastal island home on a private island. New outdoor deck/fire pit

TARPON COVE - Coastal island home on a private island. New outdoor deck/fire pit is a holiday home in Pine Island Sound, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,127.

From$296/night

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CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views!

Holiday Home, Pine Island Sound

CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views! is a holiday home in Pine Island Sound, with pool access, easy beach access, and kitchen access. This stay…

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About CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views!

CaptiVista! Your dream waterfront escape! Rustic luxury with unbelievable views! is a holiday home in Pine Island Sound, 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 $3,694.

From$322/night

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