Vacation rentals in Paradise Island, FL

340 available vacation rental offers

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Best vacation rentals and Airbnb offers in Paradise Island, FL

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly! - Paradise Island, FL
10 ★ 36 reviews

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Villa, Paradise Island

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly! is a villa in Paradise Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly! is a villa in Paradise 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, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,230.

From$176/night
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Charming County Cottage - 5 Star Rated on Leading Vacation Rental Platform! - Paradise Island, FL
10 ★ 15 reviews

Charming County Cottage - 5 Star Rated on Leading Vacation Rental Platform!

Holiday Home, Paradise Island

Charming County Cottage - 5 Star Rated on Leading Vacation Rental Platform! is a holiday home in Paradise Island, with parking and kitchen access. This stay gives travelers a comfortable…

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About Charming County Cottage - 5 Star Rated on Leading Vacation Rental Platform!

Charming County Cottage - 5 Star Rated on Leading Vacation Rental Platform! is a holiday home in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,198.

From$171/night
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Downtown Getaway Casita - Paradise Island, FL
10 ★ 14 reviews

Downtown Getaway Casita

Holiday Home, Paradise Island

Downtown Getaway Casita is a holiday home in Paradise Island, 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 Getaway Casita

Downtown Getaway Casita is a holiday home in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,070.

From$153/night
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Sunshine Eleven Getaway Sleeps 6 Bedrooms 2 and pull out couch - Paradise Island, FL
10 ★ 8 reviews

Sunshine Eleven Getaway Sleeps 6 Bedrooms 2 and pull out couch

Holiday Home, Paradise Island

Sunshine Eleven Getaway Sleeps 6 Bedrooms 2 and pull out couch is a holiday home in Paradise Island, with pet-friendly space, pool access, and room for a group. This stay gives travelers a…

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About Sunshine Eleven Getaway Sleeps 6 Bedrooms 2 and pull out couch

Sunshine Eleven Getaway Sleeps 6 Bedrooms 2 and pull out couch is a holiday home in Paradise 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,216.

From$174/night
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Waterfront vacation rentals in Paradise Island, FL

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

Private Island Old FL Waterfront Heaven on Earth - Paradise Island, FL
10 ★ 8 reviews

Private Island Old FL Waterfront Heaven on Earth

Holiday Home, Paradise Island

Private Island Old FL Waterfront Heaven on Earth is a holiday home in Paradise Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Private Island Old FL Waterfront Heaven on Earth

Private Island Old FL Waterfront Heaven on Earth is a holiday home in Paradise Island, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,015.

From$288/night
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Manatee River Bungalow-6 Boat ramp at highl shores - Paradise Island, FL
10 ★ 1 reviews

Manatee River Bungalow-6 Boat ramp at highl shores

Holiday Home, Paradise Island

Manatee River Bungalow-6 Boat ramp at highl shores is a holiday home in Paradise Island. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Manatee River Bungalow-6 Boat ramp at highl shores

Manatee River Bungalow-6 Boat ramp at highl shores is a holiday home in Paradise Island. 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, fireplace, non smoking, and adult only.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,239.

From$177/night
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Anna Maria Island -walk to the beach! - Paradise Island, FL
9.8 ★ 15 reviews

Anna Maria Island -walk to the beach!

Condo, Paradise Island

Anna Maria Island -walk to the beach! is a condo in Paradise Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Anna Maria Island -walk to the beach!

Anna Maria Island -walk to the beach! is a condo in Paradise 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: pool, hot tub, free wifi, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,201.

From$172/night
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Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental - Paradise Island, FL
9 ★ 65 reviews

Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental

Condo, Paradise Island

Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental is a condo in Paradise Island, with pool access and easy beach access. This stay gives travelers a comfortable…

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About Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental

Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental is a condo in Paradise 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: pool, hot tub, free wifi, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,327.

From$190/night
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Top cities in Paradise Island, FL

Vacation rentals and Airbnb destinationGrayton Beach State ParkVacation rentals and Airbnb destinationHenderson Beach State ParkVacation rentals and Airbnb destinationTopsail Hill Preserve State Park Gregory E. Moore RV ResortVacation rentals and Airbnb destinationBlue Mountain BeachVacation rentals and Airbnb destinationCrystal BeachVacation rentals and Airbnb destinationDestinVacation rentals and Airbnb destinationDune Allen BeachVacation rentals and Airbnb destinationFour Mile VillageVacation rentals and Airbnb destinationGrayton Beach

Family-friendly vacation rentals in Paradise Island, FL

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

Cozy new home 2 blocks from Manatee River, close to the boardwalk, and downtown - Paradise Island, FL
10 ★ 12 reviews

Cozy new home 2 blocks from Manatee River, close to the boardwalk, and downtown

Holiday Home, Paradise Island

Cozy new home 2 blocks from Manatee River, close to the boardwalk, and downtown is a holiday home in Paradise Island, with parking and kitchen access. This stay gives travelers a…

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About Cozy new home 2 blocks from Manatee River, close to the boardwalk, and downtown

Cozy new home 2 blocks from Manatee River, close to the boardwalk, and downtown is a holiday home in Paradise Island, 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, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,767.

From$252/night
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3 Mi to Downtown Bradenton: Family Home w/ Yard! - Paradise Island, FL
10 ★ 5 reviews

3 Mi to Downtown Bradenton: Family Home w/ Yard!

Holiday Home, Paradise Island

3 Mi to Downtown Bradenton: Family Home w/ Yard! is a holiday home in Paradise Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 3 Mi to Downtown Bradenton: Family Home w/ Yard!

3 Mi to Downtown Bradenton: Family Home w/ Yard! is a holiday home in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,459.

From$208/night
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Charming Modern Cottage in Sunny Palmetto - Paradise Island, FL
10 ★ 4 reviews

Charming Modern Cottage in Sunny Palmetto

Holiday Home, Paradise Island

Charming Modern Cottage in Sunny Palmetto is a holiday home in Paradise Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming Modern Cottage in Sunny Palmetto

Charming Modern Cottage in Sunny Palmetto is a holiday home in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,072.

From$296/night
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2 Mi to Riverwalk: Palmetto Gem w/ Fire Pit & BBQ - Paradise Island, FL

2 Mi to Riverwalk: Palmetto Gem w/ Fire Pit & BBQ

Cottage, Paradise Island

2 Mi to Riverwalk: Palmetto Gem w/ Fire Pit & BBQ is a cottage in Paradise Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 2 Mi to Riverwalk: Palmetto Gem w/ Fire Pit & BBQ

2 Mi to Riverwalk: Palmetto Gem w/ Fire Pit & BBQ is a cottage in Paradise Island, with 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 ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,075.

From$114/night
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Pet-friendly vacation rentals in Paradise Island, FL

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

Island Retreat by SeaBreeze Vacation - Paradise Island, FL
9.8 ★ 27 reviews

Island Retreat by SeaBreeze Vacation

Holiday Home, Paradise Island

Island Retreat by SeaBreeze Vacation is a holiday home in Paradise Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Island Retreat by SeaBreeze Vacation

Island Retreat by SeaBreeze Vacation is a holiday home in Paradise Island, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,130.

From$161/night
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Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly - Paradise Island, FL
9.8 ★ 24 reviews

Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Villa, Paradise Island

Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly is a villa in Paradise Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly is a villa in Paradise 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, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,309.

From$187/night
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Salty Anchor by Coastal Chic Vacations - Paradise Island, FL
9.8 ★ 22 reviews

Salty Anchor by Coastal Chic Vacations

Condo, Paradise Island

Salty Anchor by Coastal Chic Vacations is a condo in Paradise Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Salty Anchor by Coastal Chic Vacations

Salty Anchor by Coastal Chic Vacations is a condo in Paradise Island, 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, with kitchen, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,338.

From$191/night
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Manatee Riverfront Home , Cozy 2-bedroom house in Ellenton “Duplex”, left side. - Paradise Island, FL
9.6 ★ 15 reviews

Manatee Riverfront Home , Cozy 2-bedroom house in Ellenton “Duplex”, left side.

Holiday Home, Paradise Island

Manatee Riverfront Home , Cozy 2-bedroom house in Ellenton “Duplex”, left side. is a holiday home in Paradise Island, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Manatee Riverfront Home , Cozy 2-bedroom house in Ellenton “Duplex”, left side.

Manatee Riverfront Home , Cozy 2-bedroom house in Ellenton “Duplex”, left side. is a holiday home in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,106.

From$158/night
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Vacation rentals with a pool in Paradise Island, FL

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

Canal-Front Oasis in Terra Ceia: Pool, Patio, Dock - Paradise Island, FL
10 ★ 38 reviews

Canal-Front Oasis in Terra Ceia: Pool, Patio, Dock

Holiday Home, Paradise Island

Canal-Front Oasis in Terra Ceia: Pool, Patio, Dock is a holiday home in Paradise Island, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Canal-Front Oasis in Terra Ceia: Pool, Patio, Dock

Canal-Front Oasis in Terra Ceia: Pool, Patio, Dock is a holiday home in Paradise Island, with pool access, outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,878.

From$268/night
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Beach Daze by Coastal Chic Vacations - Paradise Island, FL
10 ★ 31 reviews

Beach Daze by Coastal Chic Vacations

Condo, Paradise Island

Beach Daze by Coastal Chic Vacations is a condo in Paradise Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beach Daze by Coastal Chic Vacations

Beach Daze by Coastal Chic Vacations is a condo in Paradise Island, 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, with kitchen, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,413.

From$202/night
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Sandy Pointe II Holmes Beach - Paradise Island, FL
9.6 ★ 61 reviews

Sandy Pointe II Holmes Beach

Condo, Paradise Island

Sandy Pointe II Holmes Beach is a condo in Paradise 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 Sandy Pointe II Holmes Beach

Sandy Pointe II Holmes Beach is a condo in Paradise 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, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,007.

From$144/night
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Landing | Amazing 1BD, Pool, Gym - Paradise Island, FL
9.6 ★ 8 reviews

Landing | Amazing 1BD, Pool, Gym

Apartment, Paradise Island

Landing · Amazing 1BD, Pool, Gym is a apartment in Paradise Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Landing | Amazing 1BD, Pool, Gym

Landing · Amazing 1BD, Pool, Gym is a apartment in Paradise Island, 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, kitchen, with kitchen, washer, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,078.

From$154/night
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Vacation rentals with parking in Paradise Island, FL

Find vacation rentals that make arriving by car easier.

Modern Top Floor Rental Unit near Anna Maria Island - Paradise Island, FL
10 ★ 8 reviews

Modern Top Floor Rental Unit near Anna Maria Island

Apartment, Paradise Island

Modern Top Floor Rental Unit near Anna Maria Island is a apartment in Paradise Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Top Floor Rental Unit near Anna Maria Island

Modern Top Floor Rental Unit near Anna Maria Island is a apartment in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,269.

From$181/night
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Modern Ground Floor Rental Unit near Anna Maria Island - Paradise Island, FL
9.4 ★ 15 reviews

Modern Ground Floor Rental Unit near Anna Maria Island

Apartment, Paradise Island

Modern Ground Floor Rental Unit near Anna Maria Island is a apartment in Paradise Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Modern Ground Floor Rental Unit near Anna Maria Island

Modern Ground Floor Rental Unit near Anna Maria Island is a apartment in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,348.

From$193/night
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Cozy Tiny home - Paradise Island, FL
9 ★ 7 reviews

Cozy Tiny home

Holiday Home, Paradise Island

Cozy Tiny home is a holiday home in Paradise Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy Tiny home

Cozy Tiny home is a holiday home in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $752.

From$107/night
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Cozy studio in pleasant Bradenton with WiFi, AC - Paradise Island, FL
8.2 ★ 10 reviews

Cozy studio in pleasant Bradenton with WiFi, AC

Apartment, Paradise Island

Cozy studio in pleasant Bradenton with WiFi, AC is a apartment in Paradise Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy studio in pleasant Bradenton with WiFi, AC

Cozy studio in pleasant Bradenton with WiFi, AC is a apartment in Paradise Island, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $578.

From$83/night
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