Vacation rentals in Harbour Island, FL

Best vacation rentals and Airbnb offers in Harbour Island, FL

10 ★ 5 reviews

Family-friendly Tampa Home < 3 Mi to Ocean!

Cottage, Harbour Island

Family-friendly Tampa Home < 3 Mi to Ocean! is a cottage in Harbour Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Family-friendly Tampa Home < 3 Mi to Ocean!

Family-friendly Tampa Home < 3 Mi to Ocean! is a cottage in Harbour 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,483.

From$163/night

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10 ★ 2 reviews

The Adaline 5 by Brightwild Classy Hyde Park Apt

Apartment, Harbour Island

The Adaline 5 by Brightwild Classy Hyde Park Apt is a apartment in Harbour Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Adaline 5 by Brightwild Classy Hyde Park Apt

The Adaline 5 by Brightwild Classy Hyde Park Apt is a apartment in Harbour Island, with 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 accessible.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,037.

From$228/night

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9.6 ★ 71 reviews

The Adaline

Apartment, Harbour Island

The Adaline is a apartment in Harbour Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Adaline

The Adaline is a apartment in Harbour 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,179.

From$249/night

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8 ★ 3 reviews

Tampa House w/ Patio, Near Downtown & Beaches!

Cottage, Harbour Island

Tampa House w/ Patio, Near Downtown & Beaches! is a cottage in Harbour Island, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Tampa House w/ Patio, Near Downtown & Beaches!

Tampa House w/ Patio, Near Downtown & Beaches! is a cottage in Harbour Island, with easy beach 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,483.

From$163/night

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Waterfront vacation rentals in Harbour Island, FL

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

Cozy 3BR South Tampa Stay Bayshore&Downtown

Holiday Home, Harbour Island

Cozy 3BR South Tampa Stay Bayshore&Downtown is a holiday home in Harbour Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Cozy 3BR South Tampa Stay Bayshore&Downtown

Cozy 3BR South Tampa Stay Bayshore&Downtown is a holiday home in Harbour Island, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,435.

From$278/night

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Huge Waterfront Mini-Resort with Gym, Dock and Pool

Holiday Home, Harbour Island

Huge Waterfront Mini-Resort with Gym, Dock and Pool is a holiday home in Harbour Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

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About Huge Waterfront Mini-Resort with Gym, Dock and Pool

Huge Waterfront Mini-Resort with Gym, Dock and Pool is a holiday home in Harbour 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $14,570.

From$1,968/night

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Relax Away in Tampa Bay

Holiday Home, Harbour Island

Relax Away in Tampa Bay is a holiday home in Harbour Island, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Relax Away in Tampa Bay

Relax Away in Tampa Bay is a holiday home in Harbour Island, with easy beach access, parking, 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, parking, paid parking, ac, and air conditioning.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,276.

From$102/night

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Family-friendly vacation rentals in Harbour Island, FL

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

10 ★ 1 reviews

3 Mi to Marina: Riverview Family Home w/ Lanai!

Cottage, Harbour Island

3 Mi to Marina: Riverview Family Home w/ Lanai! is a cottage in Harbour Island, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About 3 Mi to Marina: Riverview Family Home w/ Lanai!

3 Mi to Marina: Riverview Family Home w/ Lanai! is a cottage in Harbour 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,317.

From$248/night

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10 ★ 1 reviews

Lakefront 4-bedroom Home With Pool

Holiday Home, Harbour Island

Lakefront 4-bedroom Home With Pool is a holiday home in Harbour Island, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Lakefront 4-bedroom Home With Pool

Lakefront 4-bedroom Home With Pool is a holiday home in Harbour 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, free wifi, parking, free parking, and family friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,317.

From$260/night

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Family-Friendly Tampa Home < 3 Mi to Ocean!

Holiday Home, Harbour Island

Family-Friendly Tampa Home < 3 Mi to Ocean! is a holiday home in Harbour Island, with easy beach access, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Family-Friendly Tampa Home < 3 Mi to Ocean!

Family-Friendly Tampa Home < 3 Mi to Ocean! is a holiday home in Harbour Island, with easy beach 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, free wifi, parking, paid parking, and heating.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,428.

From$130/night

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Modern 2BR 2BA w King Bed Pool Gym 10

Apartment, Harbour Island

Modern 2BR 2BA w King Bed Pool Gym 10 is a apartment in Harbour Island, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern 2BR 2BA w King Bed Pool Gym 10

Modern 2BR 2BA w King Bed Pool Gym 10 is a apartment in Harbour Island, with 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, family friendly, kids toys, and arcade.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,413.

From$156/night

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Pet-friendly vacation rentals in Harbour Island, FL

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

Lakefront Brandon Home w/ Patio & Screened Lanai!

Holiday Home, Harbour Island

Lakefront Brandon Home w/ Patio & Screened Lanai! is a holiday home in Harbour Island, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Lakefront Brandon Home w/ Patio & Screened Lanai!

Lakefront Brandon Home w/ Patio & Screened Lanai! is a holiday home in Harbour Island, with pet-friendly space, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,908.

From$171/night

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Lakefront Brandon Home w/ Patio & Screened Lanai!

Cottage, Harbour Island

Lakefront Brandon Home w/ Patio & Screened Lanai! is a cottage in Harbour Island, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base…

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About Lakefront Brandon Home w/ Patio & Screened Lanai!

Lakefront Brandon Home w/ Patio & Screened Lanai! is a cottage in Harbour Island, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,984.

From$206/night

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Modern 2BR w Pool Pet-friendly Unit 19

Apartment, Harbour Island

Modern 2BR w Pool Pet-friendly Unit 19 is a apartment in Harbour Island, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Modern 2BR w Pool Pet-friendly Unit 19

Modern 2BR w Pool Pet-friendly Unit 19 is a apartment in Harbour Island, with pet-friendly space, pool 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, free wifi, parking, and street parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,960.

From$225/night

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Modern 2BR w Pool Pet-friendly Unit 18

Apartment, Harbour Island

Modern 2BR w Pool Pet-friendly Unit 18 is a apartment in Harbour Island, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Modern 2BR w Pool Pet-friendly Unit 18

Modern 2BR w Pool Pet-friendly Unit 18 is a apartment in Harbour Island, with pet-friendly space, pool 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, free wifi, parking, and street parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,118.

From$245/night

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Vacation rentals with a pool in Harbour Island, FL

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

Family-Friendly Tampa Home with FREE Heated Pool

Holiday Home, Harbour Island

Family-Friendly Tampa Home with FREE Heated Pool is a holiday home in Harbour Island, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable…

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About Family-Friendly Tampa Home with FREE Heated Pool

Family-Friendly Tampa Home with FREE Heated Pool is a holiday home in Harbour 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 $2,318.

From$242/night

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Casino Castaway

Holiday Home, Harbour Island

Casino Castaway is a holiday home in Harbour Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Casino Castaway

Casino Castaway is a holiday home in Harbour Island, with pool 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, parking, paid parking, and ourdoor pool.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,663.

From$131/night

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Steps to Bayshore Blvd! Snowbird Retreat w/ Pool

Cottage, Harbour Island

Steps to Bayshore Blvd! Snowbird Retreat w/ Pool is a cottage in Harbour Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base…

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About Steps to Bayshore Blvd! Snowbird Retreat w/ Pool

Steps to Bayshore Blvd! Snowbird Retreat w/ Pool is a cottage in Harbour 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,655.

From$273/night

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Davis Island Home w/ Lanai: 3 Mi to Downtown Tampa

Cottage, Harbour Island

Davis Island Home w/ Lanai: 3 Mi to Downtown Tampa is a cottage in Harbour Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Davis Island Home w/ Lanai: 3 Mi to Downtown Tampa

Davis Island Home w/ Lanai: 3 Mi to Downtown Tampa is a cottage in Harbour 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 $3,485.

From$395/night

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Vacation rentals with parking in Harbour Island, FL

Find vacation rentals that make arriving by car easier.

Walk to Hard Rock Casino: Cozy Studio!

Apartment, Harbour Island

Walk to Hard Rock Casino: Cozy Studio! is a apartment in Harbour Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Walk to Hard Rock Casino: Cozy Studio!

Walk to Hard Rock Casino: Cozy Studio! is a apartment in Harbour 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,060.

From$116/night

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The Adaline 8 Luxury Hyde Park Apt

Apartment, Harbour Island

The Adaline 8 Luxury Hyde Park Apt is a apartment in Harbour Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Adaline 8 Luxury Hyde Park Apt

The Adaline 8 Luxury Hyde Park Apt is a apartment in Harbour Island, with 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 accessible.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,994.

From$223/night

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NEW The Adaline 4 Updated Hyde Park Apt

Apartment, Harbour Island

NEW The Adaline 4 Updated Hyde Park Apt is a apartment in Harbour Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About NEW The Adaline 4 Updated Hyde Park Apt

NEW The Adaline 4 Updated Hyde Park Apt is a apartment in Harbour Island, with 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 accessible.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,016.

From$226/night

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The Adaline 2 Beautiful Hyde Park 1BR Suite

Apartment, Harbour Island

The Adaline 2 Beautiful Hyde Park 1BR Suite is a apartment in Harbour Island, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About The Adaline 2 Beautiful Hyde Park 1BR Suite

The Adaline 2 Beautiful Hyde Park 1BR Suite is a apartment in Harbour Island, with 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, free wifi, parking, free parking, and accessible.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,016.

From$226/night

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