Anna Maria Island Vacation Rentals

(227 rentals)
booking message booking message
Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$220

avg/night

$220
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

30 day stays make this condo community wonderfully quiet and special. The view overlooks the big pool and the Bay. Bring your swimsuit, we are a short distance to AMI's famous white sand beaches, umbrella, beach canopy, cooler, beach towels, and chairs make for a perfect beach day and sunset and ...

View all property information

Property Type

Anna Maria Island Condo

Show less

Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Relax in the modern 3BR 2.5Bath condo in the majestic beachfront neighborhood in Bradenton Beach, FL. Soak up the sun by the two community swimming pools, or walk down to the sandy beach and experience the beautiful Gulf Coast.The picturesque location will leave you speechless!The Space HURRICANE ...

View all property information

Property Type

Anna Maria Island Condo

Show less

Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

$459

avg/night

$459
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home is nestled among ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Location location"

Our stay at Beach Escape was lovely. The location was close to perfect. However I did leave a few recommendations for the realty people. Support from the Salty Mermaid was top notch.

See all reviews

Show less

Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms
5 reviews

$761

avg/night

$761
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

$527

avg/night

$527
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WELCOME to “Island in the Sun” ...this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Great Place to stay!"

We stayed 6 nights and had a great time. The property was clean and had everything we needed. The Florida Rental staff checked on us after we arrived to make sure everything was good. Very caring staff. ...

See all reviews

Show less

Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1123

avg/night

$1,123
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Views available from this beautiful home.This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen with gas stove, wine bar, roof top deck with sweeping views ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Ideal family vacation home!"

The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally ...

See all reviews

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.1 miles to 30 seconds to your left

$824

avg/night

$824
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This newly redesigned elevated 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and it's stunningly ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
2 reviews

$254

avg/night

$254
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to "Lazy Manatee" at Bradenton Beach Club, where even the manatees envy the level of relaxation we offer! This spiffy condo boasts three bedrooms and two full baths, giving you more space than a hermit crab's dream home. New decor, furniture and paint!At Bradenton Beach Club, ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Amazing condo"

This spacious condo appears to have been very recently completely renovated and extremely nicely updated. The large space was perfect for our group and we could have easily and comfortably added a couple ...

See all reviews

Show less

Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$313

avg/night

$313
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, new photos coming soon!*Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comfort you will come to expect from staying at one of our vacation rentals on Anna ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Distance to beach: 0.1 miles to Tampa Bay

$905

avg/night

$905
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool and mini golf.*Features include** Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Gas grill and outdoor dining * Elevated ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Sandtrap house with Beach Boutique"

Beautiful home, fantastic location and incredible service. Everything was perfect. Live the area, restaurants, biking, atmosphere and people. Super friendly. We will be back using Beach Boutique again!

See all reviews

Show less

Anna Maria Island Townhome
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

$800

avg/night

$800
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

202 69 th Street - Holmes Beach - FL 34217 VRCBook with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that ...

View all property information

Property Type

Anna Maria Island Townhome

Featured review

"Lovely stay"

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were ...

See all reviews

Show less

Anna Maria Island Townhome
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

$502

avg/night

$502
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

306 Clark drive (B) Holmes Beach, FL 34217 VRC Dog Friendly! Beautiful open concept home. 3 king bedrooms with en suites and a den with 2 single bunk beds make this property perfect for multi-generational or multi-family vacations. This home is ideally located just down the street from the white sand ...

View all property information

Property Type

Anna Maria Island Townhome

Featured review

"Beautiful Property"

Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.

See all reviews

Show less

Anna Maria Island Apartment
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to "Barefoot Mermaid 2" a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft, to white powder sand beaches of the Gulf of Mexico and less than a few flip flop ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

$179

avg/night

$179
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Paradise!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities like a heated pool, private screened lanai, and easy access to the beach, dining, and ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Great Property"

The property had everything we needed. It was very cozy! We loved the location and how it was within walking distance to everything we wanted to do. The pool was amazing! We hope to return!

See all reviews

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

$484

avg/night

$484
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called “La Cocolia” lovingly translated as the "little crab". This property is ready to host you and your family as you enjoy this newly renovated and decorated ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Just right"

The property is centrally located on the island which makes it very convenient. It has everything you need, and was very clean. We would definitely rent it again.

See all reviews

Show less

Anna Maria Island House
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

$880

avg/night

$880
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

110 11th Street South - Bradenton Beach - FL 34217Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Anna Maria week long get away"

The home was lovely. The pool and whirl pool were fabulous. Strong recommendations: TV by pool never worked. Multiple lightbulbs in lamps, etc. need to be replaced. Two blow dryers need to be replaced. ...

See all reviews

Show less

Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$676

avg/night

$676
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

*New photos are coming soon!*Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida.This ground level beach house ...

View all property information

Property Type

Anna Maria Island House

Featured review

"A True Retreat"

This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing. ...

See all reviews

Show less

Anna Maria Island House
6 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5.5 bathrooms
14 reviews

$795

avg/night

$795
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access!This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Perfect!"

This place was perfect for our family! The 4 bedrooms with King size beds and en suite baths made it so convenient for each couple. The bunk beds were perfect for the kids. The children (and adults) loved ...

See all reviews

Show less

Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$673

avg/night

$673
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Indulge in the ultimate beach escape to “Oceans Blue” located on the *premier corner* of Coconut & Los Cedros in Anna Maria. Oceans Blue is a very short walk (only 0.15 miles) to the gorgeous, white sandy beaches of Anna Maria Island, just north of Pine Ave. This *ultimate beach house* ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Bayside Beach

$957

avg/night

$957
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Just updated 2021, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Family holiday"

Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was ...

See all reviews

Show less

Anna Maria Island Apartment
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$541

avg/night

$541
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This 3 bedroom condo sits close to the Gulf Beaches at Gulf Place Condominium. Sit on the lanai and drink your coffee looking out onto the Gulf.

View all property information

Property Type

Anna Maria Island Apartment

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$519

avg/night

$519
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Create unforgettable memories at “Crescent Palms”. This *perfect island house* has been fully renovated after hurricanes Helene and Milton. Crescent Palms is centrally located, just north of Pine Avenue in Anna Maria. This home is steps away from the gorgeous white sandy beaches of Bayfront ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Peaceful and relaxing family trip"

We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa ...

See all reviews

Show less

Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

$578

avg/night

$578
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

New pictures coming by early February!Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island and a few steps from very popular Slim’s Place restaurant ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Amazing house!!"

This house was great we have been coming to the island for about 10 years! This was the best house and so close to the beach!! We will be back

See all reviews

Show less

Anna Maria Island House
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

This upper and lower unit duplex home is located steps from the Gulf of Mexico on historic Anna Maria Island. These Holmes Beach bungalows have a large heated pool and are rented in unison, perfect for friends and large families, as well. Both units are pet friendly. Only 1/2 mile from shops and restaurants ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
23 reviews

$228

avg/night

$228
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located on 5th Avenue in Holmes Beach this unit is out of the way on a dead end street. Seaduction offers a heated pool, and every amenity to make your stay here a comfortable one. There are only 4 units in the complex so to pool is "semi private".This beautiful unit sleeps six with a king ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"5 star experience"

My family enjoyed this vacation rental for a glorious week. The place was so comfy and inviting. They really thought of everything when it came to the overall experience. The property offers a nice peaceful ...

See all reviews

Show less

Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$273

avg/night

$273
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

VRC 107 78th street Holmes Beach 34217To Book Directly please visit: /chasing-wavesIf you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team:“You are vacationing in ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Great Location and Clean"

We had a great week in this unit and were pleased with many things it had. I would stay there again without hesitation. A FEW issues though with the unit. A fee of $69 for linens. We rented for 10 days ...

See all reviews

Show less

Anna Maria Island Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
7 reviews

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Blue Skies" at Bradenton Beach Club!Discover your perfect getaway in this beautifully updated three-bedroom, two-bath condo, designed for families and friends looking to unwind in style. With coastal decor and modern furnishings, you’ll feel right at home from the moment ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Beach Lovers Condo"

This condo has everything you need for the perfect vacation and then some. The location is what I thought was the best part of staying here. A short walk and before you know it, your on a beautiful white ...

See all reviews

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
owner special
Owner special: Offering Spring and Summer Discounts!

$326

avg/night

$326
avg per night
Owner special:
Offering Spring and Summer Discounts!

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

Your Own Oasis on Anna Maria Island awaits you and your family with this custom built island retreat. The large, central great room is a wonderful place to gather to share a meal or play a game, while the split bedroom configuration creates privacy. Hand scraped hardwood floors and 11' ceilings complete ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$646

avg/night

$646
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

North End Escape is a 2,300 sq. ft. Custom Built 3 bedroom 2 ½ bathroom Home featuring a 400 sq. ft. Rooftop Covered Gazebo; 750 sq. ft. of Covered Outdoor Living Area with Travertine flooring and a Heated Pool.This spacious home has wide plank hardwood flooring throughout; open concept living ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Villa
4 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 4 bathrooms
4 reviews

$228

avg/night

$228
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The ...

View all property information

Property Type

Anna Maria Island Villa

Featured review

"Huge pool and awesome location"

We had a great time and our kids loved the pool! We rented bikes and used them everyday. We had a party of 12 and it was big enough for all. We would love to stay again!

See all reviews

Show less

Anna Maria Island Condo
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
7 reviews

$452

avg/night

$452
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay ...

View all property information

Property Type

Anna Maria Island Condo

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$512

avg/night

$512
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, new photos coming soon!*Welcome to Sunrise Vista on gorgeous Anna Maria Island. Pack up the family car and head to Anna Maria Island's perfectly located beach house. Find one of the last-remaining generations owned single-family ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 3.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3.5 bathrooms
7 reviews
last minute deal
LAST MINUTE DEAL 4/14 - 5/26: Private Pool and Hot Tub! 5 night min! Sleeps 10! Pet friendly !

$580

avg/night

$580
avg per night
Offer for: Apr 14 - May 26:
Private Pool and Hot Tub! 5 night min! Sleeps 10! Pet friendly !

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Discover Your Perfect Beach Retreat at Bimini Breeze!Pack your bags (and some sunscreen) because you’re about to dive into an unforgettable getaway at Bimini Breeze! This stunning elevated home is just steps away from the pristine beaches of Anna Maria Island. With four bedrooms and three and ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Loved it!"

Our stay at the beach house was wonderful! It was very clean and well decorated. It had all the essentials we needed, and more! The pool and hot tub were so nice and private. And it is in walking distance ...

See all reviews

Show less

DEAL
Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews
owner special
Owner special: Select summer dates still available!

$347

avg/night

$347
avg per night
Owner special:
Select summer dates still available!

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches.The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Fabulous on beach condo"

This 3 bedroom, 2 bath condo in Holmes Beach was a fabulous place for our vacation of 6 retirees. From the spacious living area, open kitchen, sunny lanai, pool and good size bedrooms to being located ...

See all reviews

Show less

Anna Maria Island House
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

$255

avg/night

$255
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use the link provided below to check availability on Unit A.Unit A: Visit Unit AWelcome to “The Magic Dolphin B” an elevated vacation rental located on the northern section ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 100 yards to Manatee Beach

$314

avg/night

$314
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our home away from home on the breathtaking Anna Maria Island in the charming town of Holmes Beach Florida. Anna Maria is a barrier island on the Gulf of Mexico with an old time feel.Its only 7 miles long by 3 miles wide.Our condo is on the beach roughly 200 yds from the Gulf.We ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"In the league with the best…"

We can testify that, although there are some great gulf front places on AMI, this is among them. The interior was terrific – from the premium countertops, tiled floor, and tastefully decorated interior, ...

See all reviews

Show less

Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$602

avg/night

$602
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Discover island paradise at “Magnolia” located on Magnolia Ave., a *premier residential street* just south of Pine Ave. in Anna Maria. Magnolia is just 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island, 1 ½ blocks from the charming Ginny & Jane E’s Café, ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

$162

avg/night

$162
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. PLEASE INQUIRE AS TO AVAILABILITY OF UNIT TYPE, AS WE ARE UNABLE TO DELINEATE ON WEBSITE, THANKS! Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Great place to stay"

We recently stayed in one of the bay side units for vacation. This place is the best of both worlds. We had a view of water from our balcony but the private beach for the ocean was right across the road. ...

See all reviews

Show less

Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
owner special
Owner special: Enjoy the views at discounted rates!

$534

avg/night

$534
avg per night
Owner special:
Enjoy the views at discounted rates!

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to Bean Point Beach, Bay Front Park and the historic Pine Avenue. Enjoy shopping at ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Distance to beach: 0.1 miles to Bean Point

$901

avg/night

$901
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling home named for its spectacular porches and outdoor space.*Features include** Private heated pool and backyard oasis * Poolside lounge, bar and dining area * 85" Outdoor tv and gas ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$547

avg/night

$547
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to this Anna Maria Island vacation rental “Katmandu” just 0.15 miles or 300 steps to the wonderful white sandy beaches of the Gulf of Mexico. This property is west of Gulf Drive, with no busy roads for beach access. This property suffered minimal damage from Hurricanes Helene and Milton ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

$758

avg/night

$758
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Create unforgettable memories at “Mia Bella” located on Hammock Road, just north of Pine Avenue, in a *premier deep water canal location* in Anna Maria. Mia Bella is a short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *very spacious beach house* has been fully renovated ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Delight in Anna Maria Island"

Salty Mermaid Vacation Rental in Anna Maria Island- Even before arriving to Mia Bella, the communication with both Bella and David was incredible. They both go above and beyond to make you feel comfortable ...

See all reviews

Show less

Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4.8 rating on other travel sites

$414

avg/night

$414
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

312 A 61st Street Holmes Beach, FL 34217 VRC Welcome!Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Get ready to make memories at Crosswinds Cottage!Your home away from homeThis home has been professionally decorated and ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$399

avg/night

$399
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Need a getaway? We have the perfect spot for you. Welcome to "Sun & Surf", a direct gulf front condominium on beautiful Anna Maria Island. This 2-bedroom, 2-bathroom condominium offers all the charm and comforts you will come to expect from a Salty Mermaid Vacation Rental. This unit has ...

View all property information

Property Type

Anna Maria Island Condo

Show less

Anna Maria Island House
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

$251

avg/night

$251
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use the link provided below to check availability on Unit B.Unit B: Visit Unit BWelcome to “The Magic Dolphin A” an elevated vacation rental located on the northern section ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$276

avg/night

$276
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Bradenton Beach Club #246 “The Sea Grape”! Here is a wonderful opportunity to enjoy an updated condominium featuring 3 bedrooms and 2 full baths. Bradenton Beach Club is a great Beach to Bay complex offering many amenities such as private beach access and a boardwalk that takes ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Sea Grape Condo"

Condo was as advertised. Spacious and comfortable. Nice heated pool, not too busy. Easy walk to beach and nice beach chairs and cart to use. Indoor parking was nice to have. Hot tub was out of commission ...

See all reviews

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

$199

avg/night

$199
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Click on calendar for available 2024 dates. Book now before they are gone! CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS.TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry.20 STEPS TO THE SAND - GREAT VIEW Last minute deals don’t last long, we price to rent. We are ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Ok"

️ love this area one of my favorite places to stay AnnaMaria island.. love it .. can’t wait to go o back

See all reviews

Show less

Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*30 Day min rental @ $500/night rate + taxes and fees.Welcome to Pink Pearl – your perfect coastal escape! This stunningly renovated 4-bedroom, 3-bathroom oasis is ready to make your dream getaway a reality.Designed with both comfort and luxury in mind, this one-story home boasts a seamless ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$316

avg/night

$316
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated pool and an ...

View all property information

Property Type

Anna Maria Island Condo

Show less

Map
Expand map Close map
Anna Maria Island Vacation Rentals

Anna Maria Island Weather

 | 

7423°  5211°
JANUARY
Ocean 6518°
7624°  5412°
FEBRUARY
Ocean 6518°
7926°  5714°
MARCH
Ocean 6820°
8328°  6116°
APRIL
Ocean 7423°
8831°  6719°
MAY
Ocean 7926°
9133°  7222°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9233°  7423°
AUGUST
Ocean 8731°
9032°  7323°
SEPTEMBER
Ocean 8529°
8630°  6719°
OCTOBER
Ocean 8228°
8127°  6016°
NOVEMBER
Ocean 7624°
7624°  5412°
DECEMBER
Ocean 7021°

Enjoy the Perfect Anna Maria Island Getaway


Looking for a gorgeous and relaxing Anna Maria Island vacation rental without leaving the Florida coast? Anna Maria Island is the perfect vacation spot for you. Anna Maria Island is located on Florida’s western shore, just a few miles south of St. Petersburg.

This small, quaint island is separated from mainland Florida by the waters of Palma Sola Bay and Anna Maria Sound. However, the coast is connected to the island by way of U.S. Highways 64 and 684, making it easy to travel between the two. Despite its size, Anna Maria Island is packed with activities to enjoy and many gorgeous rental homes.

With FloridaRentals.com, you can live like a local while on your vacation by enjoying authentic architecture from the inside out within Anna Maria Island’s residential neighborhoods.

Hotel stays can be enjoyable, but there’s nothing quite like a high-quality rental home while on vacation. Not only will your trip feel more immersive within Anna Maria Island’s unique energy, but you will also be able to truly relax while on your trip.

There is no worrying about sharing a wall with strangers or lacking privacy. Additionally, you’ll be able to relax in a private backyard with some much-needed peace and quiet. Many Anna Maria rentals with FloridaRentals.com even feature unique amenities like pools, hot tubs, entertainment centers, walkable beach access, and much more.

Anna Maria Island Travel Tips


If you’re planning a trip to Anna Maria Island, you should keep a few key details in mind. The first is which airport you plan on flying into. Anna Maria Island is reachable by car from many of Florida’s largest cities, including St. Petersburg, Clearwater, Tampa, and Sarasota. However, depending on where you live, traveling to Anna Maria Island by plane might be easier.

There is no airport on the island, so you will have to fly into a nearby city and rent a car or take public transport from there. The closest commercial airport to Anna Maria Island is the Sarasota Bradenton International Airport, which is about 16 miles south of the island.

The St. Pete-Clearwater International Airport can also connect to Anna Maria Island via I-275 across Tampa Bay. This option is less convenient as this airport is about 45 miles north of the island. However, by flying into St. Pete–Clearwater, you could bundle multiple popular Florida destinations into one trip by taking the “long way.”

Another detail to keep in mind is the climate. Though many Florida cities experience warm weather throughout the year, the best time to enjoy the outdoors with warm yet pleasant temperatures on Anna Maria Island is mid-spring or fall. During these times of the year, average temperatures are between 80 and 85 degrees Fahrenheit, and chances of precipitation are low.


Best Eats on Anna Maria Island


There are many incredible restaurants and bars on Anna Maria Island, many featuring beachfront views. Rod and Reel Pier is a great example. Located on the northernmost tip of Anna Maria Island with a full menu of seafood and cocktails.

City Pier Grill and Bait, located on the end of Anna Maria Pier, is another great local spot for a meal with family, drinks with friends, or a romantic date. The delicious globally-inspired seafood dishes are complemented by the gorgeous view of Tampa Bay, which is especially breathtaking at sunset.

As you travel farther south down the island, there are many more eateries to explore during your visit to Anna Maria Island. Scott’s Deli is a great choice for fresh and delicious sandwiches if you’re looking to grab something quick to take for a picnic lunch on the beach.

Nearby are Duffy’s Tavern and Freckled Fin Irish Pub, two local bars that serve their own unique menus of American favorites and ice-cold drinks. If you’re looking for a more upscale after-dinner drinks experience, The Doctor’s Office is a hip cocktail bar in central Anna Maria with plenty of imaginative cocktails and light bites to enjoy. And yes, the building used to be a real doctor’s office!


Things to Do Near Anna Maria Island Vacation Rentals


Despite its small size, there is a huge variety of beaches to explore near Anna Maria Island rentals. Manatee Public Beach, located on the southwestern side of the island, is a popular destination for white sand, warm waters, and plenty of fun in the sun.

As you travel even farther south to the neighborhood of Bradenton Beach on Anna Maria Island, you’ll find spots like Coquina Beach, which wraps around the southern tip of the island. For prime beach access on the island’s northernmost tip, Bean Point Beach and Bayfront Park are two of the most popular. Many of the island’s beaches have a variety of amenities, such as playgrounds, volleyball nets, picnic tables, and concession stands.

The many Anna Maria Island piers are a special way to experience the beauty of the area from the water (without getting wet!). Some of these include Rod and Reel Pier, the Anna Maria City Pier, and Bridge Street Pier. Visitors can find local art and culture, gift shops, restaurants, and stunning views at any of the island’s piers.

Aside from taking a stroll along a pier, there are many other ways to experience the shimmering waters of Tampa Bay or the Gulf of Mexico. One popular activity for vacationers is to rent a boat or kayak from one of the many vendors along the island’s shores.

One of Anna Maria Island’s most popular rental shops is Beach Bums. At Beach Bums, you can rent kayaks and paddle boards for the whole family or even book a special kayak tour led by an experienced local. Need a break from the water? You can also rent bicycles or golf carts to explore Anna Maria Island by land!

Experience Bliss on Anna Maria Island


Adventure is waiting for you on Anna Maria Island. Make the most out of your adventure by vacationing at a luxurious private home, courtesy of FloridaRentals.com.


FAQ

How many vacation rentals are there in/around Anna Maria Island?

There are 227 Anna Maria Island vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Anna Maria Island?

There are vacation rentals available in Anna Maria Island for as low as $127 per night with an average price per night of $421.

Can I find a vacation rental in Anna Maria Island?

Yes, you can find vacation rentals in Anna Maria Island close to Holmes Beach, Coquina Beach, and Bradenton Beach. Don't forget to stop in to Bean Point or Manatee Public Beach.

Do any vacation rentals in Anna Maria Island have a pool?

Yes, there are 163 vacation rentals with a pool in Anna Maria Island on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Anna Maria Island vacation rentals on the ocean?

There are 18 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!