Anna Maria Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4

Vacation Rentals in Anna Maria Island

Pelican Post at Anna Maria Island Inn
Exterior

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (306)
"Great location"
Pelican Post at Anna Maria Island Inn
Bridgewalk Resort
Outdoor pool, pool umbrellas, sun loungers

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (750)
"Great location and staff were knowledgeable about surrounding areas.. "
The price is ￥38,803
￥43,848 total
includes taxes & fees
Oct 13 - Oct 14
Bridgewalk Resort
Seabreeze at Anna Maria Island Inn
Exterior

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (41)
"Awesome place to stay "
Seabreeze at Anna Maria Island Inn
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
Terrace/patio

Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

9.4 out of 10, Exceptional, (41)
"Great home with all needed comforts. Beach is right behind it when is low tide, otherwise beach access is only a block away. Home is clean, modern and comfortable with amazing sunrises. "
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Beach nearby, sun loungers, beach towels

Beach Access, heated pool, and new spa. Pickleball and playground along the bay!

9.8 out of 10, Exceptional, (288)
"Great spot! Loved the pool and spa, and the outdoor area with the grill, TV, and fridge made it super easy to hang out and relax. Nice private setup—just a few small details could be improved, but overall a really good stay. "
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Haley's at The Anna Maria Island Inn
Beach nearby, white sand, sun loungers, beach towels

Haley's at The Anna Maria Island Inn

3.0 star property
8.6 out of 10, Excellent, (375)
"The staff members were so nice and super helpful!! Place was so cute! "
Haley's at The Anna Maria Island Inn
Tradewinds Beach Resort
Private beach nearby, sun loungers, beach towels

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (383)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort
Anna Maria Sunsets - studio
Sun loungers, beach towels

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (236)
"Perfect retreat from the beach. Wonderful shower, all you need for a beach day staycation."
The price is ￥12,145
￥32,806 total
includes taxes & fees
Oct 9 - Oct 10
Anna Maria Sunsets - studio
Private Pool & Hot Tub - House close to Beach and Bridge Street
A heated pool

Private Pool & Hot Tub - House close to Beach and Bridge Street

10.0 out of 10, Exceptional, (3)
"Wonderful property that is comfortably close to beach. Everything at the property was what we needed and the downstairs area was super nice. This really is a hidden gem next to cortez beach. "
Private Pool & Hot Tub - House close to Beach and Bridge Street
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
Sun loungers, beach towels

Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt

10.0 out of 10, Exceptional, (1)
"What a beautiful home! Location was perfect, linens towels, decoration was on point! My husband had a blast with the putting green. Loved it!"
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
On the beach

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

3.0 star property
9.6 out of 10, Exceptional, (14)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
Anna Maria Sunsets - studio
Property grounds

Anna Maria Sunsets - studio

9.0 out of 10, Wonderful, (222)
" Very clean great location and property owner very nice and understanding thank you for everything "
The price is ￥15,028
￥36,172 total
includes taxes & fees
Oct 9 - Oct 10
Anna Maria Sunsets - studio
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
Interior

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

9.0 out of 10, Wonderful, (4)
"Well maintained propert and enjoyed our stay."
The price is ￥91,086
￥251,094 total
includes taxes & fees
Oct 9 - Oct 10
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Outdoor dining

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10.0 out of 10, Exceptional, (183)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Anna Maria Island - 2/1
Property grounds

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (174)
"Super cute condo so close to the beach "
The price is ￥20,494
￥53,247 total
includes taxes & fees
Oct 13 - Oct 14
Anna Maria Island - 2/1
Bay Front Condo - Anna Maria Island Sunsets
Property grounds

Bay Front Condo - Anna Maria Island Sunsets

9.8 out of 10, Exceptional, (22)
"We loved this condo. It was so clean and perfect for our family."
The price is ￥27,326
￥60,565 total
includes taxes & fees
Oct 14 - Oct 15
Bay Front Condo - Anna Maria Island Sunsets
Beachfront Home | Pool + Spa | Games | Ocean Views
A heated pool

Beachfront Home | Pool + Spa | Games | Ocean Views

10.0 out of 10, Exceptional, (38)
"This property was a dream to stay at! It truly has everything you need. The property was beautiful, all the amenities, great communication with/from owner. Our families had a wonderful vacation and can’t to come back!"
Beachfront Home | Pool + Spa | Games | Ocean Views
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
On the beach

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

9.8 out of 10, Exceptional, (121)
"Such a beautiful property! We can't wait to go back!"
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
Microwave, stovetop, dishwasher, coffee/tea maker

Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

2.0 star property
9.8 out of 10, Exceptional, (9)
"Wonderful stay ! Our family loved it ! "
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
Across from Beach, Free Golf Cart, Heated Pool, Game Room, Rooftop Deck
A heated pool

Across from Beach, Free Golf Cart, Heated Pool, Game Room, Rooftop Deck

9.6 out of 10, Exceptional, (158)
"The house was perfect for our group! The weather was perfect! Loved our time at Anna Maria Island!"
Across from Beach, Free Golf Cart, Heated Pool, Game Room, Rooftop Deck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Anna Maria Island Hotel Reviews

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

10/10 Excellent
"Beautiful and fabulous service thank you "
AMBER 1-night trip
Posted 4 days ago
Bali Hai Beachfront Resort and Spa

Find out more about Anna Maria Island

Find out more about Anna Maria Island

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