Vacation rentals in Anna Maria Island, FL

Best Vacation rentals and Airbnb offers in Anna Maria Island, FL

Spinnakers Cottages - Cabin 1 - Dog Friendly - 250 Steps to Beach, Pool

Holiday Home, Anna Maria Island

Spinnakers Cottages - Cabin 1 - Dog Friendly - 250 Steps to Beach, Pool is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

Read more

About Spinnakers Cottages - Cabin 1 - Dog Friendly - 250 Steps to Beach, Pool

Spinnakers Cottages - Cabin 1 - Dog Friendly - 250 Steps to Beach, Pool is a holiday home in Anna Maria 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,319.

From$100/night

Show›

Holmes Beach Bungalow - B

Holiday Home, Anna Maria Island

Holmes Beach Bungalow - B is a holiday home in Anna Maria Island, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Holmes Beach Bungalow - B

Holmes Beach Bungalow - B is a holiday home in Anna Maria Island, with 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, ac, air conditioning, heating, and accessible.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,412.

From$101/night

Show›

Gulf Haven East! 5-minute walk to the Gulf!

Holiday Home, Anna Maria Island

Gulf Haven East! 5-minute walk to the Gulf! is a holiday home in Anna Maria Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Gulf Haven East! 5-minute walk to the Gulf!

Gulf Haven East! 5-minute walk to the Gulf! is a holiday home in Anna Maria Island, 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 $1,433.

From$110/night

Show›

Gulf Haven West! 5- minute walk to the Gulf!

Holiday Home, Anna Maria Island

Gulf Haven West! 5- minute walk to the Gulf! is a holiday home in Anna Maria Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Gulf Haven West! 5- minute walk to the Gulf!

Gulf Haven West! 5- minute walk to the Gulf! is a holiday home in Anna Maria Island, 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 $1,433.

From$110/night

Show›

Browse Waterfront Vacation Rentals in Anna Maria Island, FL

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

Private Home with Pool, Near the Beach - Sand Dollar

Holiday Home, Anna Maria Island

Private Home with Pool, Near the Beach - Sand Dollar is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Private Home with Pool, Near the Beach - Sand Dollar

Private Home with Pool, Near the Beach - Sand Dollar is a holiday home in Anna Maria 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,621.

From$204/night

Show›

Happy Place: 1.5 Blocks to Beach, Pool Home, Florida Room by Anna Maria Life Vacation Rentals

Holiday Home, Anna Maria Island

Happy Place: 1.5 Blocks to Beach, Pool Home, Florida Room by Anna Maria Life Vacation Rentals is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen…

Read more

About Happy Place: 1.5 Blocks to Beach, Pool Home, Florida Room by Anna Maria Life Vacation Rentals

Happy Place: 1.5 Blocks to Beach, Pool Home, Florida Room by Anna Maria Life Vacation Rentals is a holiday home in Anna Maria 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, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,885.

From$224/night

Show›

Beach getaway pool, spa, mini golf, walk to beach

Holiday Home, Anna Maria Island

Beach getaway pool, spa, mini golf, walk to beach is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Beach getaway pool, spa, mini golf, walk to beach

Beach getaway pool, spa, mini golf, walk to beach is a holiday home in Anna Maria 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,187.

From$225/night

Show›

Pool, Spa, Mini Golf, Games, Beach, sleeps 6

Holiday Home, Anna Maria Island

Pool, Spa, Mini Golf, Games, Beach, sleeps 6 is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

Read more

About Pool, Spa, Mini Golf, Games, Beach, sleeps 6

Pool, Spa, Mini Golf, Games, Beach, sleeps 6 is a holiday home in Anna Maria 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,275.

From$226/night

Show›

Browse Vacation Rentals with a Pool in Anna Maria Island, FL

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

Sugaree - 2bedroom Private Pool Property in Holmes Beach

Condo, Anna Maria Island

Sugaree - 2bedroom Private Pool Property in Holmes Beach is a condo in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Sugaree - 2bedroom Private Pool Property in Holmes Beach

Sugaree - 2bedroom Private Pool Property in Holmes Beach is a condo in Anna Maria 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,072.

From$183/night

Show›

SS Salamander North · Pool & Fire Pit · Beach

Holiday Home, Anna Maria Island

SS Salamander North · Pool & Fire Pit · Beach is a holiday home in Anna Maria Island, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

Read more

About SS Salamander North · Pool & Fire Pit · Beach

SS Salamander North · Pool & Fire Pit · Beach is a holiday home in Anna Maria 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,180.

From$187/night

Show›

SS Salamander South · 2 Full Baths · Heated Pool

Holiday Home, Anna Maria Island

SS Salamander South · 2 Full Baths · Heated Pool is a holiday home in Anna Maria Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About SS Salamander South · 2 Full Baths · Heated Pool

SS Salamander South · 2 Full Baths · Heated Pool is a holiday home in Anna Maria Island, 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 $2,187.

From$188/night

Show›

Cute Home with pool, spa, mini golf walk to beach!

Holiday Home, Anna Maria Island

Cute Home with pool, spa, mini golf walk to beach! is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Cute Home with pool, spa, mini golf walk to beach!

Cute Home with pool, spa, mini golf walk to beach! is a holiday home in Anna Maria 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,929.

From$199/night

Show›

Best Anna Maria Island, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.

Condo, Anna Maria Island

Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point. is a condo in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives…

Read more

About Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.

Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point. is a condo in Anna Maria 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,656.

From$138/night

Show›

Minnow 2 Villa

Villa, Anna Maria Island

Minnow 2 Villa is a villa in Anna Maria Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

Read more

About Minnow 2 Villa

Minnow 2 Villa is a villa in Anna Maria 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: parking, paid parking, ac, air conditioning, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,447.

From$189/night

Show›

Peace 'n Paradise · Pool & Spa · 300 Yds Gulf

Holiday Home, Anna Maria Island

Peace 'n Paradise · Pool & Spa · 300 Yds Gulf is a holiday home in Anna Maria Island, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

Read more

About Peace 'n Paradise · Pool & Spa · 300 Yds Gulf

Peace 'n Paradise · Pool & Spa · 300 Yds Gulf is a holiday home in Anna Maria 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,239.

From$195/night

Show›

Peacock Paradise

Holiday Home, Anna Maria Island

Peacock Paradise is a holiday home in Anna Maria Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Peacock Paradise

Peacock Paradise is a holiday home in Anna Maria Island, 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 $2,208.

From$225/night

Show›

Best Pet-Friendly Vacation Rentals in Anna Maria Island, FL

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

Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals

Holiday Home, Anna Maria Island

Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals is a holiday home in Anna Maria Island, with pool access, easy beach access, and kitchen…

Read more

About Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals

Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals is a holiday home in Anna Maria 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, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,325.

From$182/night

Show›

Sand Dollar Beach Side Villa

Villa, Anna Maria Island

Sand Dollar Beach Side Villa is a villa in Anna Maria Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Sand Dollar Beach Side Villa

Sand Dollar Beach Side Villa is a villa in Anna Maria 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, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,913.

From$183/night

Show›

Laid-Back Island Home with Pool! Walk to Beach

Holiday Home, Anna Maria Island

Laid-Back Island Home with Pool! Walk to Beach is a holiday home in Anna Maria Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

Read more

About Laid-Back Island Home with Pool! Walk to Beach

Laid-Back Island Home with Pool! Walk to Beach is a holiday home in Anna Maria 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,520.

From$205/night

Show›

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!

Holiday Home, Anna Maria Island

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly! is a holiday home in Anna Maria Island, with pet-friendly space, parking, and kitchen access. This stay gives…

Read more

About Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly! is a holiday home in Anna Maria 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,603.

From$210/night

Show›

Best Anna Maria Island, FL vacation rentals with a kitchen

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

Bollinger B · Pet-Friendly · Half Block to Gulf

Holiday Home, Anna Maria Island

Bollinger B · Pet-Friendly · Half Block to Gulf is a holiday home in Anna Maria Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About Bollinger B · Pet-Friendly · Half Block to Gulf

Bollinger B · Pet-Friendly · Half Block to Gulf is a holiday home in Anna Maria Island, 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 $1,471.

From$112/night

Show›

Pink Peacock

Holiday Home, Anna Maria Island

Pink Peacock is a holiday home in Anna Maria Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Pink Peacock

Pink Peacock is a holiday home in Anna Maria 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, pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,953.

From$200/night

Show›

Paradise - Steps to the Beach

Holiday Home, Anna Maria Island

Paradise - Steps to the Beach is a holiday home in Anna Maria Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Paradise - Steps to the Beach

Paradise - Steps to the Beach is a holiday home in Anna Maria 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,171.

From$229/night

Show›

Island Townhouse - 200 Steps to the Beach

Holiday Home, Anna Maria Island

Island Townhouse - 200 Steps to the Beach is a holiday home in Anna Maria Island, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Island Townhouse - 200 Steps to the Beach

Island Townhouse - 200 Steps to the Beach is a holiday home in Anna Maria Island, 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: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,201.

From$230/night

Show›