50 Best Anna Maria Island Vacation rentals on Holiday Lettings - Beach rentals

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116 properties

Anna Maria Island

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2,635 Vacation rentals

(37) Excellent 

41

Townhouse rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Our modern, luxury townhouse within the Bermuda Bay Club condominium enjoys a fantastic location right at the beach on Bradenton Beach; within easy walking to a number of shops, restaurants and a host of activities. Packed with all the mod cons (including free WiFi, tel …see more

from $172 / night

$1,200 - $1,900 / week

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from $172 / night

(1) Excellent 

8

Anna Maria Island Vacation apartment rental

Florida / Anna Maria Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our apartment is located in close proximity to one of the most beautiful beaches of Florida. The apartment has a master bedroom with king size bed, TV, bathroom with shower or shower basin and toilet and a sep. Guest room with adjoining bath towels and linens are provid …see more

from $112 / night

$784 - $1,400 / week

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avg. 3 hours 59 minutes

from $112 / night

11

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 60 nights min

  • 2 bedrooms
  • Sleeps 6
  • 60 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful island condo is newly refurbished and redecorated for a perfect get-away. This quiet, 55+ community is a paradise. Situated in Anna Maria Island, Florida, the island has quiet, old-Florida charm with numerous restaurants, shops, and conveniences. A fre …see more

from $94 / night

$654 / week

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from $94 / night

(5) Excellent 

29

Vacation home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.274 mi
  • Swimming pool
  • Child friendly
Situated on beautiful Anna Maria Island. This beautiful ground floor condo overlooks Palma Solar Bay. Tampa Bay is just 300 yards away with a wonderful golden beach. Watch the breathtaking sunrise every morning from the lani or master bedroom. 1250 sq.ft of luxury acc …see more

from $129 / night

$900 / week

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from $129 / night

16

Vacation townhouse in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 6 90 nights min

  • 3 bedrooms
  • Sleeps 6
  • 90 nights min
  • Child friendly
At the entrance to Anna Maria Island, on Perico Island overlooking Anna Maria Sound is the gorgeous 220-acre island oasis and Florida’s newest private waterfront resort. Within this gated community is our fully furnished southern coastal coach home, which features 3 be …see more

from $250 / night

$1,750 / week

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avg. 2 hours 20 minutes

from $250 / night

(1) Excellent 

14

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has 2 full size beds. Its just steps t …see more

from $130 / night

$720 - $995 / week

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avg. 1 hour 32 minutes

from $130 / night

48

Anna Maria Island Vacation home rental

Florida / Anna Maria Island

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Many homes with a high bedrooms count sprung out on the island lately, designed to maximize rents, they are built on very small lots normally 50 ft wide and packed upwards in three levels . This is a well reviewed house that I built for me and my family in 1998, it is …see more

from $700 / night

$3,500 - $4,900 / week

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from $700 / night

(1) Excellent 

20

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps …see more

from $156 / night

$1,090 - $1,695 / week

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avg. 1 hour 32 minutes

from $156 / night

(5) Very Good 

20

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,650 / week

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avg. 1 hour 32 minutes

from $200 / night

(29) Excellent 

52

Vacation home rental

Anna Maria Island / Holmes Beach

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood …see more

from $269 / night

$1,883 / week

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avg. 54 minutes

from $269 / night

25

Anna Maria Vacation home accommodation

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Bask in the endless sunshine of Anna Maria Island at this three-bedroom home, a dog-friendly Florida escape with a private canalfront dock, its very own heated pool and a wondrous location only two blocks from the beach. This sleek, light-filled home is located on the …see more

from $193 / night

$1,351 / week

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avg. 32 minutes

from $193 / night

(24) Excellent 

Certificate of Excellence

32

Vacation home accommodation

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
**DISCOUNTS FOR RENTALS OF 28 NIGHTS OR MORE ANY TIME OF YEAR** *****PLEASE ASK US ABOUT SPECIAL PRICING FOR YOUR STAY***** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - ADDED AUGUST 2014 TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GAR …see more

Certificate of Excellence

from $229 / night

$1,600 - $2,500 / week

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from $229 / night

(1) Excellent 

19

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,695 / week

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avg. 1 hour 32 minutes

from $200 / night

29

Vacation home rental

Anna Maria Island / Anna Maria

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Say goodbye to stress and hello to island vibes at this spacious beach house. Featuring a private yard with tropical greenery, a dog-friendly attitude, and a great location near the beach and pier, this house will have you living in a dream! Sitting near the northern t …see more

from $136 / night

$952 / week

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avg. 32 minutes

from $136 / night

(6) Excellent 

15

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Just half a block to the beach and steps to our fishing dock on Sarasota Bay, these cute and cozy apartments offer a great vacation value on Anna Maria Island. Watch the sunrise from the dock every morning and cap your busy day with sunset over the Gulf of Mexico. White …see more

from $125 / night

$795 - $1,145 / week

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avg. 3 hours 2 minutes

from $125 / night

30

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Enjoy your own slice of island life with a stay at this charming, two-bedroom, waterfront condo. Located in a quiet, but vibrant neighborhood with plenty of local island flavor, there's room here for up to four guests along with the family dog for an additional nightly …see more

from $115 / night

$805 / week

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avg. 32 minutes

from $115 / night

28

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Fall in love with this adorable, renovated island bungalow! Your location near the beach is hard to beat, and the outdoor sitting area ensures you're never far from the ocean breeze. Stay a while with the family or a group of friends and experience life on Anna Maria Is …see more

from $110 / night

$770 / week

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avg. 32 minutes

from $110 / night

31

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Your ultimate Florida getaway starts right here at this ideally located 2-bedroom, 2-bathroom vacation rental condo situated right on the beach. Boasting 1,500 square feet and accommodations for up to 6, this open concept condo offers direct access to Holmes Beach and w …see more

from $185 / night

$1,295 / week

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avg. 19 minutes

from $185 / night

23

Vacation villa rental

Anna Maria Island / Holmes Beach

1 8 Min stay varies

  • 1 bedroom
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room …see more

from $200 / night

$1,090 - $1,750 / week

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avg. 1 hour 32 minutes

from $200 / night

(1) Excellent 

14

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,695 / week

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Responds fast!
avg. 1 hour 32 minutes

from $200 / night

(5) Very Good 

17

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,695 / week

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avg. 1 hour 32 minutes

from $200 / night

24

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Find cool island comfort at this two-bedroom Holmes Beach escape, a bright, spacious home with a dog-friendly interior, a screened-in balcony, free WiFi, and a perfectly walkable location close to the beach and the free island trolley. You'll find this home in the nort …see more

from $122 / night

$854 / week

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avg. 32 minutes

from $122 / night

(2) Very Good 

42

Cottage rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

4 15 Min stay varies

  • 4 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
We have some openings available April 8-15! Our family has lovingly restored this HISTORIC 1939 FISHING CAMP located on beautiful Sarasota Bay. You'll be surrounded by water living on the narrowest point of Anna Maria Island. Sugar sand BEACH only a 1 minute stroll a …see more

from $115 / night

$800 - $1,400 / week

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from $115 / night

19

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,695 / week

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avg. 1 hour 32 minutes

from $200 / night

(2) Very Good 

15

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Relax in the casual comfort of an island paradise, and have a true Old Florida experience on Anna Maria Island, where riding bikes is the preferred way to travel and indulging in the simple pleasures of life - sun, beach, scuba dive, Snorkel and relaxation are the favo …see more

from $150 / night

$1,000 / week

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from $150 / night

(2) Excellent 

25

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from yo …see more

from $299 / night

$2,093 / week

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avg. 2 hours 24 minutes

from $299 / night

26

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Welcome to this charming, dog-friendly Anna Maria Island house. With the private heated pool and hot tub, you will feel like you're miles away from your worries. There is a large, fenced-in backyard with lush landscaping, where you can soak up the warm island sun from a …see more

from $172 / night

$1,204 / week

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avg. 32 minutes

from $172 / night

(5) Very Good 

15

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitch …see more

from $150 / night

$825 - $1,350 / week

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avg. 1 hour 32 minutes

from $150 / night

30

Vacation home rental

Anna Maria Island / Anna Maria

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. Distance to the Beach: 50 yards This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and b …see more

from $200 / night

$1,400 - $2,310 / week

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from $200 / night

(1) Excellent 

17

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Updated 2 bedroom townhouse condo in Bradenton Beach with an unobstructed view of the Gulf of Mexico. Grab your beach chairs, umbrella, cooler and towels (provided) cross Gulf Drive and you're on the beach in a minute. If your enjoy fishing, the pier extending out into …see more

from $140 / night

$980 - $1,050 / week

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avg. 3 hours 23 minutes

from $140 / night

(2) Excellent 

31

Vacation cottage with swimming pool in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fir …see more

from $225 / night

$1,240 / week

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avg. 2 hours 29 minutes

from $225 / night

35

Bradenton Beach Vacation home rental

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Enjoy an incredible beach vacation at this safari-themed rental with designer decor throughout and a well-appointed Key West-style patio. Feel the warm sea breeze off the Gulf of Mexico and listen as the waves roll across the sugar soft sands at the neighboring beach, d …see more

from $108 / night

$756 / week

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avg. 32 minutes

from $108 / night

(1) Excellent 

12

Bradenton Beach Vacation studio rental

Anna Maria Island / Bradenton Beach

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
This beachfront vacation rental is perfectly suited for a family of 4 or a couple looking for a weekend getaway. The rental is in Bradenton Beach and equipped with 1 California King and 2 twin sleepers. The balcony features a fantastic view of the Gulf of Mexico where y …see more

from $108 / night

$745 - $1,764 / week

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from $108 / night

29

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Make this beautiful 3-bedroom, 2.5-bath vacation rental house your new home-away-from-home in Holmes Beach! Up to 6 travelers will have the luxury of swimming in the private pool or hot tub after kayaking in Palma Sola Bay. Take the provided wagon to the Gulf Beach a me …see more

from $235 / night

$1,645 / week

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avg. 19 minutes

from $235 / night

(1) Excellent 

14

Vacation condo in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Relax in the casual comfort of an island paradise, and have a true Old Florida experience on Anna Maria Island, where riding bikes is the preferred way to travel and indulging in the simple pleasures of life - sun, beach, scuba dive, Snorkel and relaxation are th …see more

from $150 / night

$850 / week

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from $150 / night

56

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Experience luxury living at this three-bedroom seaside home with a fireplace, tropical accents, casually sophisticated decor, and updated amenities. Spend lazy days by the heated pool or stroll out to the adjacent Gulf-front beach, with its powdery quartz sand, blue wat …see more

from $286 / night

$2,002 / week

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avg. 32 minutes

from $286 / night

(1) Excellent 

34

Bradenton Beach Vacation condo accommodation

Anna Maria Island / Bradenton Beach

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Location, location, location. The 3 most important things to consider in a vacation rental. Tucked back on a VERY peaceful setting. Brick patio courtyard and PRIVATE outdoor covered patio set with umbrella. This is a desired ground level end unit in a Key West styled 4 …see more

from $189 / night

$1,199 - $2,395 / week

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from $189 / night

(2) Very Good 

35

Vacation villa in Anna Maria

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the h …see more

from $119 / night

$795 - $1,480 / week

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from $119 / night

18

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,695 / week

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avg. 1 hour 32 minutes

from $200 / night

(11) Excellent 

Certificate of Excellence

27

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, …see more

Certificate of Excellence

from $250 / night

$1,250 - $1,500 / week

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avg. 2 hours 28 minutes

from $250 / night