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Luxury Vacation Rentals in Anna Maria Island

(56 rentals)
Anna Maria Island House
Sleeps 14, 5 bedrooms, 4 bathrooms
18 reviews

Key Amenities

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

About this property

Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's the perfect...

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Featured review

"Breathe Inn"

Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....

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$794
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 4 Bedrooms | 4.5 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome...

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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...

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$1,025
avg per night
Anna Maria Island House
Sleeps 12, 5 bedrooms, 5 bathrooms
4 reviews

Key Amenities

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

About this property

Vitamin Sea by Beach Retreats Vacation Rentals 146 Crescent Dr, Anna Maria, FL 34216 Welcome to Vitamin Sea, a stunning 5-bedroom, 5-bath luxury retreat located on the coveted north end of Anna Maria Island, just a 10-minute stroll to Bean Point Beach. With a private dock, heated saltwater pool and...

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Featured review

"Paradise"

Vitamin Sea exceeded all expectations for our week's vacation for our family of 12. Location was perfect for daily visits to both sides of the island. House is stunning and fully equipped for swimming,...

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$1,207
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 5 bathrooms
2 reviews

Distance to beach: 0.1 miles to Bayside Beach

Key Amenities

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

About this property

Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep 14 total with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms...

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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...

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$882
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
7 reviews

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...

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$789
avg per night

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Anna Maria Island House
Sleeps 16, 6 bedrooms, 4 bathrooms
6 reviews

Distance to beach: 45 feet to Gulf of Mexico

Key Amenities

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

About this property

Enjoy breathtaking views of Egmont Key, Tampa Bay, and the Gulf of Mexico right from your doorstep! Walk straight ahead and you are on North Bay Boulevard Beach. Walk 4 more lots to the left and you are on Bean Point! Or walk 5 lots further left and you are on the Gulf of Mexico. Perfectly situated next...

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$981
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 2 bathrooms
4 reviews

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 160 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...

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Featured review

"Family vacation"

We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...

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$767
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

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

Key Amenities

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

About this property

This newly redesigned elevated pet friendly 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...

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$737
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Island Escape by Beach Retreats Vacation Rentals 307 65th St, Holmes Beach, FL 34217 VRC18-000047 Your dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions....

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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...

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$874
avg per night
Anna Maria Island House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared Dock Luxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...

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$916
avg per night
Anna Maria Island Townhome
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Oasis by the Beach by Beach Retreats Vacation Rentals 202 69th St, Holmes Beach, FL 34217 VRC17-000120 5 Bedrooms | 4 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Book with confidence: No cancellation...

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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...

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$792
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 4 bathrooms
4 reviews

Key Amenities

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

About this property

110 11th Street South - Bradenton Beach - FL 34217 No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60...

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Featured review

"Family vacation"

The house was beautiful, lots of space to spread out with a family of 12. Location was perfect, beach on one side and bay on the other. Had everything we needed for cooking, pool, and relaxing. Pool was...

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$922
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms
1 review

Key Amenities

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

About this property

Just Beachy – Your Luxury Island Retreat on Anna Maria Island 128 49th Street Holmes Beach FL 34217 VRC21-000019 4 Bedrooms + nanny suite | 6 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub | This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Escape...

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Featured review

"Great Thanksgiving Vacation!"

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its...

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$1,000
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
3 reviews

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...

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Featured review

"The perfect getaway"

The entire stay was above all expectations. It was my wife's birthday. We invited friends from out of town to celebrate with us. The place was roomy and very comfortable. The kitchen is fantastic with the...

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$1,306
avg per night
New
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Salt + Sol | Canal-Front Oasis + NEW Heated Pool + Golf Cart | North End Retreat Welcome to Salt + Sol, your serene canal-front escape on the coveted north end of Anna Maria Island. This bright and breezy 4-bedroom home blends relaxed coastal elegance with modern comfort — all just minutes from...

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$855
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach! Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for...

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$1,190
avg per night
New
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Steps to Beach + Heated Pool + Golf Cart & Bikes | North End Retreat This beautifully remodeled 4-bedroom, 4-bath Anna Maria Island vacation home is perfectly situated on the coveted north end — just steps from the Gulf of Mexico. With a convenient beach access path directly across the street,...

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$825
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

VRC16-000137 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 offers 4 bedrooms,...

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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....

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$840
avg per night
Anna Maria Island House
Sleeps 12, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in...

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$742
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

NO CANCELLATION FEES: $500 deposit due at time of booking; balance due 60 days prior to arrival Cancel 60+ days before arrival → Full refund (no fees). Cancel within 60 days of arrival → No refund. Cancellations must be made in writing and received by Beach Retreats on or before the...

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Featured review

"Excellent place to stay!"

This house was incredible! Absolutely beautiful, well stocked, an amazing pool and outdoor setup, and so conveniently located! While it's not beach-front, it's just a house or two away from the beach entrance...

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$906
avg per night
Anna Maria Island House
Sleeps 12, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Get ready to pack your bags because you'll be escaping to a tranquil oasis nestled within a lush tropical backyard, where a shimmering pool and soothing spa await your relaxation. Discover the serene charm of A Bean Point Paradise, a retreat boasting 5 bedrooms and 4.5 bathrooms with parking for...

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$925
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms
2 reviews

Key Amenities

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

About this property

Paradise Found - with Pool & Hot Tub 401 42nd Street, Holmes Beach, FL 34217 VRC17-000010 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub ​​​​​​​ Pet Friendly This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation...

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Featured review

"Paradise Found"

We rented this home for time with our kids and grandkids. It worked great! The rooms were spacious and it was great that every room had a bathroom. We had no issues. The kitchen was well stocked. The backyard...

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$851
avg per night
Anna Maria Island Condo
Sleeps 10, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Sunset Penthouse at Bradenton Beach Club, where top-floor luxury meets picture-perfect Gulf views. Step into the family room and be greeted by sweeping panoramas of Bradenton Beach. This 4-bedroom, 2.5-bathroom penthouse is thoughtfully designed for comfort, style, and effortless coastal...

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$788
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to “Salty Sunsets” on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy access to Bean Point. This Anna Maria Island vacation rental home offers all the goodies to make sure your vacation does not skip a beat. This beautiful property offers...

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$922
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$788
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • 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 completely restored after hurricanes Helene and Milton. This...

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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...

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$764
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Escape to paradise at our stunning vacation rental, located at 230 Lakeview on beautiful Anna Maria Island. This exquisite property offers the ultimate coastal getaway, boasting a brand-new pool and spa where you can unwind and soak up the Florida sun in style. For those seeking outdoor fun, our rental...

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$1,116
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 6 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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Featured review

"Great getaway !"

A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .

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$867
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms

Key Amenities

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

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! Welcome to your home-away-from-home! This 4-bedroom, 4 full bath, 2 half bath pet-friendly, canal-front retreat is made for making memories — whether you're here with family, friends, or your fishing crew. From sunrise to sunset, the views,...

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$985
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Paradise Beach House – Luxury 5-Bedroom Retreat with Pool & Jacuzzi 403 42nd Street, Holmes Beach, FL 34217 VRC 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome to Paradise...

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$898
avg per night
Anna Maria Island House
Sleeps 12, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$877
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Angel Sea by Beach Retreats Vacation Rentals VRC19-000188 4118 5th Ave, Holmes Beach, FL 34217 6 Bedrooms | 3.5 Bathrooms | Sleeps 12 | Elevator | Heated Pool & Hot Tub This home can park up to 4 vehicles Welcome to Angel Sea—a stunning 6-bedroom, 3.5-bathroom vacation home designed...

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Featured review

"Family vacation"

House was very comfortable. Everything was as advertised. Pool heater was not working when we checked in. They offered us the use of the pool next door. It was very kind and made our trip perfect.

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$890
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Footprints in the Sand 114 48th Street Holmes Beach FL 34217 VRC19-000156 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome to FootPrints in the Sand, a stunning vacation...

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$765
avg per night
Anna Maria Island House
Sleeps 12, 4 bedrooms, 3 bathrooms
1 review

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...

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Featured review

"Great place"

We loved our stay at Anchor Splash, the house is beautiful and it is a great location. The beds were very comfortable the pillows not so much. One of the TVs did not work in one of our bedrooms with the...

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$746
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Mermaid's Crossing by Beach Retreats Vacation Rentals 210 65th St, Holmes Beach, FL 34217 VRC17-000007 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation fees! Cancel 60+...

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Featured review

"Yearly family vacation"

Location was good with only a short walk to the beach and in a quiet location. House was clean and there was plenty of room for the group. Lots of pool and beach toys for us and the kids. The pool needed...

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$711
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Bimini Sunrise special: Concierge Collection Property Golf cart included! Anna Maria on Anna Maria Island - A short walk to Pine Avenue Spacious heated pool / spa Rooftop deck, elevator, private dock, kayaks, paddleboards Gas grill (propane included) Professional...

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$1,288
avg per night
Anna Maria Island House
Sleeps 16, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$1,195
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Coastal Serenity has a rooftop deck, private pool and spa, and an EV Charger! This single family home boasts 4 bedrooms and 3.5 bathrooms and is only a three minute walk to the beach. Beautifully decorated, the kitchen is fully-equipped with a wet bar and an island with ample counter space allowing for...

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$773
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$853
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces....

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$788
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

Key Amenities

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

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

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.

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$834
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Bring your family and guests to this 2-unit house! About 40 steps to the beach entrance of Anna Maria white, sandy beach, this home combined boasts 5 bedrooms, a sleeper sofa and 5 bathrooms. Bean Point Unit A boasts 3 bedrooms/3 bathrooms, while Unit B has 2 bedrooms/2 bathrooms. Both units feature well-equipped...

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$914
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$1,106
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

Featured review

"Very nice home"

Home was very nice. The whole backyard is like paradise. Overall great experience. Pool was not refreshing but probably expected this time of year in Florida. The hot tub flows over into pool when...

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$804
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6 bathrooms

Key Amenities

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

About this property

Welcome to Shangri-La, an idyllic vacation rental nestled on the exclusive tip of Anna Maria Island at Bean Point. This luxurious, fenced, and gated private property offers an escape from the everyday, inviting you to unwind and rejuvenate in a setting of unparalleled beauty and comfort. Available for...

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$4,000
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

Discover Serendipity: Your Pet-Friendly Beachfront Haven on Anna Maria Island Beachfront Bliss Awaits You Indulge in the enchantment of beachfront bliss at Serendipity, an exceptional 4-bedroom home perfectly positioned on the coveted North End of Anna Maria Island. This tranquil escape beckons you...

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$1,500
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms

Key Amenities

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

About this property

Welcome to paradise! This beachfront blends modernity with relaxation to give your group a heavenly experience. Located in a prime location on the North End of Anna Maria Island, Cloud 9 has everything that your group needs for a perfect vacation. Each of the 4 bedrooms is professionally decorated and...

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$2,422
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Luxury and the beach intersect at a point titled Serendipity Deux. This gorgeous 4 bedroom home offers all the allure of an extravagantly decorated space while giving you premium beach access and an ideal location. The Master Suite is located on the first level and comes outfitted with a king bed, tub...

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$2,500
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

About this property

Welcome to Waves - Your Perfect Anna Maria Island Getaway! Experience the ultimate beach retreat at Waves, a luxurious 4-bedroom, 3-bathroom vacation home located on the picturesque Anna Maria Island. Nestled just across the street from the sun-kissed sands and azure waters of the beach, this property...

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$1,008
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Beachfront paradise awaits you at the TripleTail. Located in a prime location - just one block from Pine Avenue and the City Pier, the 4 bed/4 bath bayfront home offers everything you need for the perfect vacation. On the ground floor, you’ll find a beachfront king bedroom, along with a...

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$2,000
avg per night
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