Vacation Rentals & Beach Rentals in Anna Maria Island

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39 beach rentals

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children's pool Sauna

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Price per night from

$206

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Children's pool Sauna

All filters match

Price per night from

$114

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Sauna

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Price per night from

$173

These homes match some but not all of your filters. Clear all filters

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$574

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: Sauna, Children's pool

1 of 2 filters match

Price per night from

$574

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: Sauna, Children's pool

1 of 2 filters match

Price per night from

$259

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$150

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$213

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$861

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$224

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$173

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: Sauna, Children's pool

1 of 2 filters match

Price per night from

$477

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sauna, Children's pool

1 of 2 filters match

Price per night from

$192

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$218

Lovely Siesta Key 3BR 2.5BA Condo, Island Paradise

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$493

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$276

Perfecto's Suite #2

Bay Pines apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$167

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$115

Condo on the Key

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$207

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$166

2 bedroom condo, Coquina Key, Tampa Bay, Florida

St. Petersburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Waterside at Coquina Key has it all!” Waterside at Coquina Key is a a well kept up gated community that offers all the amenities a wonderful vacation requires. Marlean's condo provides a nicely updated unit that allows you to enjoy the waterside condos in comfort and provides all the extra's you need to relax and unwind in the peace and tranquility of a watersdie property. The kitchen had all you needed and more and was nicely updated and contained all you need to cook in or prepare a quick breakfast and take off for the pool or to work-out. The only small downside is not to have a wash and dryer available in the unit. Although one is available 24/7 as the clubhouse and you can use your debit card to work them. the beds were comfortable, and the living area had ample seating available. Thank your for shring your condo, it was wonderful.

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$144

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$107

REDUCED FOR APRIL!

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$171

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$209

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$437

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$905

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$345

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$1,032

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$178

Waterfront and Walkable to Best Of Madeira Beach! 2 Blocks to the Sand!

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$102

Starfish Haven at Runaway Bay 201

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$165

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$454

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$804

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$516

Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$345

Runaway Bay unit 192 bay view 2bed/2Bath - Bradenton Beach - Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$194

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Sauna

1 of 2 filters match

Price per night from

$563

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rentals in Anna Maria Island

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