Vacation Rentals & Beach Rentals in Anna Maria Island

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79 beach rentals

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Housekeeping Included

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Price per night from

$172

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1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$572

CFP! St.PeteBeach Rental for 4! 01/09-11/2017. College Football Nat'l Champs

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$572

Remodeled Sunset Vistas 303N - Booking for Summer 2021, with No Cleaning Fees!

Treasure Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$258

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$149

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$212

Queen Bed Room at Palm Grove Inn Downtown St Pete

St. Petersburg hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$343

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$858

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$223

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$160

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$172

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$286

NEW! Staying with friends or family? Ask them to rent you a GuestWing!

St. Petersburg caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$205

St Pete Beach fun in sun!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$155

Tiny Treasure - Stunning waterfront condo with dock (102)

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$228

Sarasota Waterfront and Marina Community with Tikki Bar and Grill

North Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$102

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$475

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$205

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$191

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Housekeeping Included, Children's pool

1 of 2 filters match

Price per night from

$114

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$409

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$194

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$77

Sunset Suite

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$172

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$275

Perfecto's Suite #2

Bay Pines apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$166

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$104

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$234

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$482

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$332

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$286

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$343

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$271

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$429

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$228

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$343

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$1,373

Spacious clean quiet home facing the Boca Ciega Bay in Isla del Sol

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Housekeeping Included

1 of 2 filters match

Price per night from

$166

Viewing 38 of 79
rentals in Anna Maria Island

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