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

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103 properties

Anna Maria Island

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2,141 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

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

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

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 - $2,800 / week

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avg. 28 minutes

from $235 / night

(1) Excellent 

12

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 $130 / night

$900 - $1,000 / week

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from $130 / 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 $150 / night

$895 - $1,480 / week

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from $150 / night

(1) Excellent 

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

(24) Excellent 

Certificate of Excellence

17

Vacation cottage in Bradenton Beach

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
You will enjoy this adorable newly renovated vacation cottage – THE LITTLE MERMAID -- on Anna Maria Island just across the street from the Gulf of Mexico and minutes from shopping and attractions on Bradenton Beach’s popular Bridge Street! Your three parking spaces are …see more

Certificate of Excellence

from $130 / night

$850 - $895 / week

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Responds fast!
avg. 3 hours 47 minutes

from $130 / 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 $117 / night

$819 / week

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Responds fast!
avg. 1 hour 7 minutes

from $117 / night

25

Bradenton Beach Vacation cottage rental

Anna Maria Island / Bradenton Beach

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Car not necessary
This STAND ALONE, VERY CHARMING, cottage is in a very peaceful setting with huge brick courtyard. This is not like most other vacation rentals that require you to climb 1-2 stories. This is a stand alone ground level home! We have just invested in a new kitchen, bathro …see more

from $199 / night

$995 - $2,290 / week

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from $199 / night

(1) Good 

15

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
Gulf Watch 211 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 6 people. Beautiful Gulf to Bay Island Living!~ Distance to the Beach: across the street Gulf Watch Condo---2 bedroom, 2 bath condo in 32 unit complex with heated pool. Gulf to Bay sett …see more

from $136 / night

$950 - $1,375 / week

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from $136 / 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. 1 hour 7 minutes

from $122 / night

(2) Excellent 

22

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a me …see more

from $175 / night

$1,400 - $3,500 / week

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Responds fast!
avg. 1 hour 14 minutes

from $175 / night

(13) Very Good 

12

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beachy and bright condo on the second floor of a small 2-story-building (20 units in total), overlooking the mangroves with view to the Palma Sola Bay. Only some steps away from the ocean and the wonderful wide and powder sanded beaches. The condo is recently refurnishe …see more

from $105 / night

$700 - $1,400 / week

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from $105 / night

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Swimming pool
Very spacious two bedroom Condo with a large living room. Flat Screen TV, fully equipped kitchen with all the appliances. Not far from the beach, and short distance to area shopping. Unit has heated pool, and a relaxing Pool deck area. Main bedroom has a King size bed w …see more

from $145 / night

$795 - $1,350 / week

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from $145 / 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 - $1,715 / week

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avg. 47 minutes

from $185 / night

23

Vacation home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
LUXURY RENOVATED 2 BR/2 BA ISLAND CONDO - DIRECTLY ON GULF OF MEXICO Private, Peaceful, Comfortable * Relax, Rejuvenate * Screened-in Dining Balcony/w Hi-Back Swivel Rockers, Overlooking Heated Pool, Beach and Gulf of Mexico * Spectacular Water Views, Nightly Show at …see more

from $121 / night

$850 - $2,100 / week

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from $121 / night

34

Bradenton Beach Vacation home rental

Anna Maria Island / Bradenton Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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. We have the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from the …see more

from $195 / night

$1,365 / week

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from $195 / 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 

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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Responds fast!
avg. 3 hours 12 minutes

from $225 / night

29

Bradenton Beach Vacation studio rental

Anna Maria Island / Bradenton Beach

Studio 4 1 night min

  • Studio
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
Club Bamboo South unit 224, Gulf Front Studio, ocean view, maximum occupancy of 4 people. Community pool, community BBQ grill. Beautiful Gulf Front Studio directly on the Gulf of Mexico! Open the sliding glass doors to the covered private balcony and listen to the soun …see more

from $167 / night

$1,168 - $1,754 / week

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from $167 / night

37

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
Runaway Bay 274 - Across the street from the beach- Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. Located directly across the street from the white sandy beaches of the Gulf of Mexico, this large 2 bedroom, 2 bath, 2nd floor unit has been completely remodele …see more

from $129 / night

$900 - $1,700 / week

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from $129 / night

35

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
This cozy duplex with a shared pool and easy beach access is waiting for your upcoming Anna Maria Island vacation. You'll be in close proximity to dining and shopping, and you'll have space to park two cars. This rental is located two blocks from flour soft, sugar whi …see more

from $122 / night

$854 / week

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avg. 1 hour 7 minutes

from $122 / night

47

Bradenton Beach Vacation condo rental

Anna Maria Island / Bradenton Beach

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
In resort style community beautiful 2 Bedroom, 2 Bathroom top floor units in very private setting! Located in Bradenton, only a short drive to Florida’s most beautiful beaches on Anna Maria Island. Sit on the porch and enjoy the sunset. The high ceilings unit is very …see more

from $130 / night

$910 - $1,050 / week

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from $130 / night

(28) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $269 / night

$1,883 / week

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Responds fast!
avg. 54 minutes

from $269 / night

17

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
Three bedroom condo directly overlooking the Gulf of Mexico. Watch the dolphins while eating your breakfast or the beautiful Gulf sunsets over wine or while eating dinner. Master bedroom has a king size bed and en suite bathroom with shower and walk-in closet. Second …see more

from $185 / night

$1,295 / week

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from $185 / night

(33) Excellent 

24

Vacation home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. Yo …see more

from $135 / night

$850 - $1,350 / week

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avg. 2 hours 43 minutes

from $135 / night

23

Vacation villa rental

Anna Maria Island / Holmes Beach

1 8 Min stay varies

  • 1 bedroom
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
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. 3 hours 7 minutes

from $200 / night

(2) Excellent 

39

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
  • Swimming pool
  • Child friendly
The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. Th …see more

from $257 / night

$1,800 - $3,600 / week

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Responds fast!
avg. 1 hour 1 minutes

from $257 / night

(1) Very Good 

11

Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool
Gorgeous Efficiency and steps to white sandy beaches from this 1 bedroom, 1 bath elevated vacation rental, one story up overlooking pool area. Stairs go up to small deck in front of the efficiency. With 3 x 8 open deck to enjoy the sunsets, or overlooking pool. Feel th …see more

from $125 / night

$700 - $950 / week

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from $125 / night

37

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
You'll fall in love with the island life in no time when you stay at this canal front Anna Maria vacation rental! Platinum-rated and featuring a private pool, private spa, and three parking spots, this home features all the amenities you need for a relaxing Florida beac …see more

from $243 / night

$1,701 / week

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avg. 1 hour 7 minutes

from $243 / night

29

Bradenton Beach Vacation studio rental

Anna Maria Island / Bradenton Beach

Studio 4 1 night min

  • Studio
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
Club Bamboo South unit 220, Gulf Front Studio, ocean view, maximum occupancy of 4 people. Community pool, community BBQ grill. MAGNIFICENT SUNSETS - RESTFUL DAYS This beautiful, modern condo is directly on the white sand beaches of the Gulf of Mexico. The view is amaz …see more

from $167 / night

$1,168 - $1,754 / week

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from $167 / night

(3) Good 

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Car not necessary
  • 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 a king size bed. Its just step …see more

from $130 / night

$720 - $995 / week

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Responds fast!
avg. 3 hours 7 minutes

from $130 / night

16

Vacation townhouse in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Key West Style Townhouse with a beautiful Gulf, Beach view in Anna Maria Island. This large townhouse with 3 bedrooms, 3 1/2 baths multi level front unit is the ideal location for family. Overlooking Gulf Drive North located on the West Coast of Florida, Anna Maria Isl …see more

from $269 / night

$1,799 / week

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from $269 / night

(1) Excellent 

31

Vacation apartment 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 mi
  • Swimming pool
DESCRIPTION: Welcome to your perfect Florida vacation! This bright and beachy 2-bedroom, 2-bathroom condo accommodates 6 and is newly updated and tastefully decorated to wrap you with the comforts of home, yet with a distinctive beach appeal. Located just off of Bradent …see more

from $129 / night

$900 - $1,250 / week

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from $129 / night

(2) Excellent 

21

Bradenton Beach Vacation condo rental

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
This condo has just been totally renovated and redecorated in a contemporary yet comfortable style. The apartment is a ground floor unit with easy access to the pool, Gulf of Mexico and Bay of Sarasota. Runaway Bay resort features 13 acres of lush landscaping and is ful …see more

from $139 / night

$969 - $1,850 / week

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Responds fast!
avg. 3 hours 24 minutes

from $139 / night

32

Vacation apartment accommodation

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
Sandy Point 114 - Condo 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. Distance to the Beach: 4 blocks. VRC16-000070 This 2 bedroom , 3 bath townhouse condo features 2 living floors and 3 verandas above an enclosed over-sized garage and located in the Cove at Sandy …see more

from $122 / night

$850 - $1,760 / week

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from $122 / night

57

Vacation home with shared pool in Anna Maria

Anna Maria Island / Anna Maria

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 Block Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat opti …see more

from $275 / night

$1,800 - $2,420 / week

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from $275 / night

19

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Pelican Cove 11 - Across the street from the beach- Condo 2 Bedroom /2 Bath bay view, maximum occupancy of 4 people. Florida's Finest Beach to Bay Resort with a Community pool! Pelican Cove is a small, private complex with heated pool and spa, tennis court, and larg …see more

from $200 / night

$1,200 - $1,800 / week

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from $200 / night