Anna Maria Island Vacation Rentals with Private Pool

(114 rentals)
booking message booking message
Anna Maria Island House | On the beach
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

$825

avg/night

$825
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 House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$664

avg/night

$664
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Anna Maria Island Beach Palace offers incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf of Mexico is merely 75 yards to the west, and Florida’s Intracoastal Waterway ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House | On the beach
2 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 2 bedrooms, 2 bathrooms

$252

avg/night

$252
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool
  • WiFi

About this property

The Salty Mermaid Team is excited to introduce our newest property, The Haven Unit 1 and Unit 2! *This property requires a 7-night minimum stay. Arrival and departure days must fall on a Saturday* When booking this listing, you will be reserving both Units at this Duplex. Haverkos on Holmes- ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House | On the beach
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
12 reviews

$332

avg/night

$332
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

Featured review

"Great Vacation Spot. Great Owner. Awesome Location"

What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...

See all reviews

Show less

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

$199

avg/night

$199
avg per night
View Details

Key Amenities

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

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided - sleeps 4, 2 bedroom/2 bath, very private and quiet - all linens provided, washer/dryer in unit - stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin Donuts/ Baskin Robbins, beach stores, Ace Hardware, ...

View all property information

Property Type

Anna Maria Island Condo

Featured review

"Great condo!"

We enjoyed our stay! The condo was clean, spacious & inviting! The location was wonderful. We will definitely stay again. The owner was very quick to reply to my emails.

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

$730

avg/night

$730
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 Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
5 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

"Perfect place"

We have stayed here several times over the last years. It is always immaculate inside. The kitchen is well stocked. The beds are very comfortable. It’s become our home away from home. The ocean is ...

See all reviews

Show less

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

$324

avg/night

$324
avg per night
View Details

Key Amenities

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

About this property

Come experience Unit 204 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 ...

View all property information

Property Type

Anna Maria Island Condo

Show less

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

$513

avg/night

$513
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island! The decor is a perfect blend of coastal elegance and comfort, featuring ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
31 reviews

$553

avg/night

$553
avg per night
View Details

Key Amenities

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

About this property

We have developed a comprehensive Safety / Cleaning / Sanitation Plan and work with an amazing team to ensure the home & pool are sparkling clean for all of our guests. Our home goes through rigorous cleaning per CDC guidelines using only EPA approved detergent and highest MERV 13 A/C filters changed ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Great house"

We had a remarkable time at this house. The location, pool and house exceeded our expectations. We'll come back.

See all reviews

Show less

Anna Maria Island House
5 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 2 bathrooms
2 reviews

$875

avg/night

$875
avg per night
View Details

Key Amenities

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

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 150 five-star ratings from Airbnb/VRBO! Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Hidden paradise"

We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...

See all reviews

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

$938

avg/night

$938
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* * Ultimate vacation home with elevator^ * Private heated pool and backyard oasis * Poolside lounge, bar and dining ...

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
2 reviews

$1226

avg/night

$1,226
avg per night
View Details

Key Amenities

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

About this property

Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Best Place On Anna Maria"

Hosts are fabulous! very responsive and caring! House is amazing! our friends and family were blown away by how much attention to detail they put in to the furnishings and the home itself! A true paradise!

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

$796

avg/night

$796
avg per night
View Details

Key Amenities

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

About this property

What You'll Love About This Home: Location! 3 Blocks to the Beach! 4 Bedrooms / 4 Bathrooms 3 King Beds, Two Sets of Bunk Beds with Twin Bed over Full Bed Lagoon Style Heated Pool w/ sundeck & Spa In Pool Umbrellas Pool Deck Lounge Chairs Poolside Covered Lounge with Patio Furniture, ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House | On the beach
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms

$252

avg/night

$252
avg per night
View Details

Key Amenities

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

About this property

The Salty Mermaid Team is excited to introduce our newest property, The Haven Unit 1 and Unit 2! *This property requires a 7-night minimum stay. Arrival and departure days must fall on a Saturday* When booking this listing, you will be reserving both Units at this Duplex. Haverkos on Holmes- ...

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

$571

avg/night

$571
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

*Under new owners, and new property management* 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 located west of Gulf drive, with no busy roads to cross for beach access. ...

View all property information

Property Type

Anna Maria Island House

Show less

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

$698

avg/night

$698
avg per night
View Details

Key Amenities

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

About this property

Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for ...

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
2 reviews

$677

avg/night

$677
avg per night
View Details

Key Amenities

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

About this property

Welcome to “Pineapple Cottage” – a beautifully updated ground level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants and fun on Pine Avenue. This charming cottage has been professionally decorated and offers all the luxuries you will ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Great Property"

This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay ...

See all reviews

Show less

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

$487

avg/night

$487
avg per night
View Details

Key Amenities

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

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 | On the beach
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$432

avg/night

$432
avg per night
View Details

Key Amenities

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

About this property

Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside ...

View all property information

Property Type

Anna Maria Island House

Show less

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

$644

avg/night

$644
avg per night
View Details

Key Amenities

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

About this property

️ Anna Maria Island is open and ready to welcome you! ️ The beaches are as beautiful as ever, and most of the island’s favorite restaurants and shops are open for you to enjoy! ---- Escape to your own tropical paradise at this stunning villa on Anna Maria Island! This beautiful property ...

View all property information

Property Type

Anna Maria Island Villa

Featured review

"Beautiful house and Celine is an excellent host"

Beautiful house and Celine is an excellent host. We stayed here a week for a family vacation and really enjoyed our time. House had everything we needed and more. Very clean and super close to the beach. ...

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

$1094

avg/night

$1,094
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 | On the beach
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

$669

avg/night

$669
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
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$288

avg/night

$288
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy our beautiful island. 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 ...

View all property information

Property Type

Anna Maria Island Condo

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

$919

avg/night

$919
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • 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, spa and mini golf. *Features include* * Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Standalone Hot Tub * Gas grill ...

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 Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$422

avg/night

$422
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

The Beach Sands condo is completely surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. The Beach Sands offers the best location on Anna Maria Island where the island is only 150 yards wide. Our complex ...

View all property information

Property Type

Anna Maria Island Condo

Show less

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

$420

avg/night

$420
avg per night
View Details

Key Amenities

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

About this property

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

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

Key Amenities

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

About this property

Welcome to Gone Coastal 3! This quaint three bedroom, two bathrooms plus a half bath vacation home is located just a short walk from Anna Maria Island’s sugar white sands and crystal clear waters! Beach towels, six beach chairs, and a beach wagon are provided to ensure your days spent in the sun ...

View all property information

Property Type

Anna Maria Island House

Show less

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

$218

avg/night

$218
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • 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 | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
1 review

Distance to beach: 0.1 miles to Beach Access 45th St

$563

avg/night

$563
avg per night
View Details

Key Amenities

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

About this property

Address of Areca Cove: 206 N Harbor Drive, Holmes Beach, FL 34217 ARECA COVE - A bright and wonderful 4 bedroom/ 3.5 bath home just a 3-minute walk away from an astonishing white sand beach. With a heated pool in tropical and private surroundings, a covered patio by the pool area and multiple balconies ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Perfect home and wonderful hosts!"

Olaf and Marissa were wonderful hosts - welcoming and responsive. Their home was absolutely perfect for a family get together with mixed ages. They have everything you need for a beach stay and the space ...

See all reviews

Show less

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

Distance to beach: 0.1 miles to Beach Access 45th St

$487

avg/night

$487
avg per night
View Details

Key Amenities

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

About this property

Address of Manatee Watch: 205 N Harbor Drive, Holmes Beach, FL 34217 MANATEE WATCH - A marvelous waterfront 3 bedroom/ 2 bath home just a short walk away from an astonishing white sand beach. Heated pool, hot tub and a spacious dock with beautiful views of the canal. Many months each year you can watch ...

View all property information

Property Type

Anna Maria Island House

Show less

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

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach. Inside it has a split plan with a king sized bedroom and a second bedroom with ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Perfect beach location with beautiful interior"

This duplex includes stunning beachy interior decorating, great location (quiet neighborhood with an easy walk to a white sands beach) with a bonus heated pool with outdoor shower, which was ideal after ...

See all reviews

Show less

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

Key Amenities

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

About this property

Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach. Inside it has a split plan with a king sized bedroom and a second bedroom ...

View all property information

Property Type

Anna Maria Island House

Show less

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

$580

avg/night

$580
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Colorful and inviting with a vibrant tropical style, Carefree Cottage is a perfectly-named oasis in Holmes Beach where all of your cares melt away the moment you walk through the front door. Located on a quiet residential street that offers plenty of peace and privacy yet keeps you close to the beaches ...

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
3 reviews

$770

avg/night

$770
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

VRC If Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay. This stunningly built and decorated 4 bedroom + Bunk Den 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Pleasantly surprised"

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly ...

See all reviews

Show less

Anna Maria Island House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$420

avg/night

$420
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Casa Bonita is bright, inviting, and the perfect place for a wonderful vacation with family and friends in a tropical paradise. This home is located in the heart of Bradenton Beach, only a few short steps away from beachfront access and Bridge Street. You can lounge in the sun and enjoy a swim in your ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Perfect"

The house was absolutely perfect! It was so nice and the cleanest house we have ever rented. We had everything we needed. We would definitely recommend.

See all reviews

Show less

Anna Maria Island House
8 BR | 5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 5 bathrooms
3 reviews

$983

avg/night

$983
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Looking for a relaxing island retreat just steps from the soft white sand and turquoise waters in Bradenton Beach on Anna Maria Island? Look no further for your perfect vacation home for the whole family. Island Oasis is a custom-built spacious 8 bedroom/5 bathroom was professionally furnished to provide ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Nice"

Very clean nice home enjoyed it...would consider renting again..thank you...talked with the owner and manager next door Great people

See all reviews

Show less

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

$616

avg/night

$616
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE BETWEEN ! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Stonehenge is a massive stone monument in southern England. Here in the U.S. on Anna Maria Island, ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4.7 rating on other travel sites

$816

avg/night

$816
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedroom oasis. Located on the idyllic north end, Anchor Splash is a short stroll from the white sandy beaches and warm, aquamarine gulf waters. It's also within walking distance ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms
2 reviews

$1308

avg/night

$1,308
avg per night
View Details

Key Amenities

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

About this property

Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, an elevator and a rooftop deck boasting amazing views of the Gulf of Mexico. This 9 bedroom, 8.5 bathroom, pet-friendly abode is an ideal beach retreat suitable for multiple families ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Great location"

Very clean and comfortable. Easy walk to everything you need and want to do. I would stay there again and highly recommend.

See all reviews

Show less

Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms

$1330

avg/night

$1,330
avg per night
View Details

Key Amenities

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

About this property

Get ready to be swept off your feet by the charm and luxury of Winding Waves, your dream vacation spot right on the beautiful Anna Maria Island. This dazzling nine-bedroom, eight-and-a-half bathroom beachfront home is all about fun in the sun and upscale relaxation! Splash and Play Outdoors: Dive ...

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
4.9 rating on other travel sites

$365

avg/night

$365
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming pet-friendly home just steps to the beaches. Misty Beach is a charming coastal home with a flamingo-shaded exterior, quickly moving you onto island time. The interior showcases island artwork, creating a welcoming and calming environment. ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$326

avg/night

$326
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming home just steps to the beaches. The home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria Hideaway lies within a stone's throw of the trolley stops for guests to hop on ...

View all property information

Property Type

Anna Maria Island House

Featured review

"great location"

We enjoyed on our stay at this well-kept property on Anna Maria Island. It offered privacy with a good central location.

See all reviews

Show less

Anna Maria Island House
5 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 6.5 bathrooms
4.8 rating on other travel sites

$923

avg/night

$923
avg per night
View Details

Key Amenities

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

About this property

Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 5 bathrooms
5.0 rating on other travel sites

$1078

avg/night

$1,078
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Slice of Paradise VRC 216 68th St - Holmes Beach - FL - 34217 This stunning custom built and decorated 4 bedroom 5.5 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico. Located in prime Holmes Beach you are with in walking distance to the award winning Beach Bistro ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

$762

avg/night

$762
avg per night
View Details

Key Amenities

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

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance This gorgeous, custom-built, professionally designed, private home is a 4 bedroom/6.5 ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Better than i expected."

Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.

See all reviews

Show less

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

$2060

avg/night

$2,060
avg per night
View Details

Key Amenities

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

About this property

Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king ...

View all property information

Property Type

Anna Maria Island House

Show less

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

$1164

avg/night

$1,164
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beachfront, North End, large 2 bedroom with expansive views of the dolphins frolicking in the azure waters of the North End of Anna Maria Island. BBQ grill, bikes, paddle boards, and kayaks are all included. Your backyard is a beautiful view of Egmont Key & the Skyway Bridge and your front yard is ...

View all property information

Property Type

Anna Maria Island House

Show less

Anna Maria Island House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

$556

avg/night

$556
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 steps) ...

View all property information

Property Type

Anna Maria Island House

Featured review

"Perfect Beach House for just about anyone"

Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first ...

See all reviews

Show less

Anna Maria Island House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$514

avg/night

$514
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Costa Lotta is "home away from home”. All the amenities you will need in this 2,100 sq.ft. home. Costa Lotta is the perfect vacation spot for relaxation on Anna Maria Island! Just 200 steps and you are on a gorgeous, white sandy beach looking at the spectacular Gulf of Mexico! Walking distance ...

View all property information

Property Type

Anna Maria Island House

Show less

Map
Expand map Close map
Anna Maria Island Vacation Rentals