Holiday Homes in Anna Maria

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Featured Holiday Homes in Anna Maria

Aerial view
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
10.0 out of 10, Exceptional, (103)
"Beautiful house in a great location! Enjoyed everything about it!"
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
Beach
4 Beds 4.5 Bath with Pool 3 Blocks to Beach
10.0 out of 10, Exceptional, (68)
"We have rented with Patrick (the owner) before and this time was as enjoyable as always. The house is in great condition and Patrick is always available and able to help us with any questions/requests. To be honest, his response time is simply amazing; he gets back to me so fast any time I reach out. This property, with an incredible pool/hot tub set up and proximity to down town and the beach cant be beat. Highly recommend and we are already hoping to go back next year!"
4 Beds 4.5 Bath with Pool 3 Blocks to Beach
Property grounds
Escape to an island adventure!
10.0 out of 10, Exceptional, (95)
"House was very spacious for a family of four with teenage boys. We loved the screened in porch in the front and the downstairs screened in room for games and movie night. This place is located half way between the gulf on one side and the bay on the other. Both a short enough distance to walk or bike. Located near shopping and restaurants too but on a quiet street. Home had everything you need. Kitchen was well equip with staple items like oils, seasonings, sugar, etc. Lots of beach towels,...
Escape to an island adventure!
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Property grounds
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
10.0 out of 10, Exceptional, (8)
"Very roomy rental with multiple amenities right in the heart of it all!"
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
Pool
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
10.0 out of 10, Exceptional, (97)
"This was our 2nd year staying at Rum Cove and we would definitely book this house again. The property managers were very responsive to one minor issue that we had on check in. The house is in walking distance to the beach, the pier and many restaurants and shops."
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
View from property
Updated, Charming Florida Cottage
10.0 out of 10, Exceptional, (24)
"It was our first time on Anna Marie Island. The location was great towards most things and the property was perfect/above expectations for us! I think we'll book again next year!!!"
Updated, Charming Florida Cottage
Aerial view
Sea 'Esta in Anna Maria, FL
10.0 out of 10, Exceptional, (15)
"Perfect for us."
Sea 'Esta in Anna Maria, FL
Pool
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
10.0 out of 10, Exceptional, (179)
"This year two for us and we adore this villa whenever we visit AMI. It's a solid 5/5 across the board. With the boat dock, mornings are effortless; we wake up, get ready, hop on the boat and head straight to the beach or fishing spots. Giovanna, the host, is fantastic; communication with her is top-notch. The house easily accommodates our entire family. Looking forward to returning in the future!"
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
Terrace/patio
Zen Beach Cottage: Beautiful ground level home steps to beach
10.0 out of 10, Exceptional, (11)
"Zen Beach Cottage exceeded our exceptions in every way! From the tasteful decor, the cozy and serene property, to the quiet neighborhood, our visit to beautiful Anna Maria was enhanced by this gorgeous property.We especially enjoyed the abundant light and short walk to the beach access path. The host was quick to respond to any questions and comments. Our only request is an upgrade on the mattresses, they squeak and creak upon any movement. Also, the 3rd bedroom/den shows a futon while its...
Zen Beach Cottage: Beautiful ground level home steps to beach
Property grounds
Gulfview Estate: Beachfront luxury home with sweeping Gulf views
10.0 out of 10, Exceptional, (4)
"The house, location, pool, view, and beach access! Simply gorgeous! Beyond my expectations! Overall, clean and well furnished! Amazing grill, but grease prevented us from using. Reported to property manager. Confident it will be tended to. Plenty of beach towels, beach chairs, sand toys! Only one bath towel, hand towel, and wash cloth per occupant. Bring your own toiletries, toilet paper and paper towels. Having said that, I’d love to stay again! Very nice!"
Gulfview Estate: Beachfront luxury home with sweeping Gulf views
Fridge, microwave, oven, stovetop
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining
10.0 out of 10, Exceptional, (11)
"This home was super clean, was a great fit for our family of 5, the pool area was very nice, and the beach super close. We loved it!"
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining
Beach nearby, sun-loungers, beach towels
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
9.8 out of 10, Exceptional, (63)
"We booked this adorable two bedroom duplex for four nights to go to Anna Maria for a family wedding. We had no idea about the island and ended up in the loveliest quiet little neighborhood in beans point. The unit was exactly as it was described and as it looks in the pictures, the owner was incredibly responsive and helpful and I would highly recommend this adorable spot for anyone looking for an affordable, immaculate, quiet place on the island."
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
A heated pool
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
9.8 out of 10, Exceptional, (100)
"We enjoyed our stay at Bay - Canal Waterfront! We enjoyed the amenities - the pool is beautiful, large and in the sun all day but plenty of shady areas if you want that too. The kayaks were enjoyed as well and we did have some manatee sightings! We enjoyed the golf cart as well! The layout of the house is 2 separate areas with a full unit on top and on bottom. The only complaint we had which cannot be controlled by the owner is the smell of the muck that congregates at the end of the canal which...
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
Beach
Bay Breeze Cottages #1 (The Mahi-Mahi)
9.8 out of 10, Exceptional, (70)
"Great little place. Nicely updated, very clean, great location. Loved having golf cart included. The pool was wonderful, private, very pretty and lots of patio furniture. Really enjoyed our first stay ion AMI."
Bay Breeze Cottages #1 (The Mahi-Mahi)
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (157)
"The location and views were incredible! It was so great being right on the beach and it was easy to walk everywhere. Unfortunately the house is a little tired, the refrigerator should be replaced as the door doesn’t close well, the shower head in the primary bathroom should be replaced and the pillows/mattresses need updating. Again, the location and views are stunning and we had the best time playing on the beach and in the water all day, but for the expensive cost per night, we were...
The price is NZ$1,359
per night
12 Jun - 13 Jun
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Exterior
Bean Point Gem awaits your stay!
9.6 out of 10, Exceptional, (167)
"We thoroughly enjoyed our stay and would book again in a heartbeat. The location is amazing, property was clean and well stocked. Our family loved it!"
Bean Point Gem awaits your stay!
Outdoor pool, a heated pool
Naut 2 Shabby Cottage | Next-Level Pool Area, Darling FL Cottage - Best of Both!
9.6 out of 10, Exceptional, (65)
"Artsy fun house comfortable and convenient to everything! Clean inside and out for the perfect family beach vacation!! I could live there!!"
Naut 2 Shabby Cottage | Next-Level Pool Area, Darling FL Cottage - Best of Both!
A heated pool
Canal front home with a private Pool, Spa and Waterslide! The kids will love it!
9.6 out of 10, Exceptional, (38)
"My husband and I had a wonderful vacation with our two daughters and their family. The house provided us with the comfort of a home away from home in the warm Florida Sun"
Canal front home with a private Pool, Spa and Waterslide! The kids will love it!
Property grounds
SPECTACULAR 3 BED/2BATH w/Heated Pool & Spa FREE WiFi & Trolley, Close to...
9.6 out of 10, Exceptional, (49)
"Half of the trip the hot tub was broken and the pool did not have heat. The owners fully replaced the heater, so hopefully there are no issues going forward. For our trip it took 3 days to resolve."
SPECTACULAR 3 BED/2BATH w/Heated Pool & Spa FREE WiFi & Trolley, Close to...
Pool
Mermaid House Rooftop deck, Gulf views, beautiful home, steps to the sand!
9.6 out of 10, Exceptional, (18)
"Perfect to enjoy the beach close to everything walking the greatest is how close you are to the beach. We will definitely arrange to visit it again."
Mermaid House Rooftop deck, Gulf views, beautiful home, steps to the sand!
Don't see what you're looking for?
See all available properties in Anna Maria
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Anna Maria

Beach nearby, sun-loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (232)
"We were lucky enough to find this home in the heart of everywhere we needed to be. Wedding was at The Sandbar… 7 minute walk. Cindy’s house was spotless and thank god had enough coffee for us the first morning. Plenty of towels too! Very nice. Thank you for being exactly as promissed."
Charming cottage in quiet area, close to beach & bay.
Beach nearby, sun-loungers, beach towels
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
9.8 out of 10, Exceptional, (63)
"We booked this adorable two bedroom duplex for four nights to go to Anna Maria for a family wedding. We had no idea about the island and ended up in the loveliest quiet little neighborhood in beans point. The unit was exactly as it was described and as it looks in the pictures, the owner was incredibly responsive and helpful and I would highly recommend this adorable spot for anyone looking for an affordable, immaculate, quiet place on the island."
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
A heated pool
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
9.8 out of 10, Exceptional, (100)
"We enjoyed our stay at Bay - Canal Waterfront! We enjoyed the amenities - the pool is beautiful, large and in the sun all day but plenty of shady areas if you want that too. The kayaks were enjoyed as well and we did have some manatee sightings! We enjoyed the golf cart as well! The layout of the house is 2 separate areas with a full unit on top and on bottom. The only complaint we had which cannot be controlled by the owner is the smell of the muck that congregates at the end of the canal which...
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.