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

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Anna Maria Island

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840 Vacation rentals

(5) Excellent 

28

Vacation condo in Anna Maria Island

Florida / Anna Maria Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in the heart of Anna Maria Island in the sun-drenched community of Holmes Beach is 'Seacrest' where you can enjoy island living at its best in this stunning destination.Our light & roomy 2 bedroom condo (one of only four in a quiet location being in a little cul …see more

from $102 / night

$711 - $1767 / week

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avg. 3 hours 54 minutes

from $102 / night

(1) Excellent 

11

Anna Maria Island Vacation home rental

Florida / Anna Maria Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
The Beach House is situated on one of the quietest areas of the beautiful white sandy beach, that stretches from one end of the island to the other. A nature lovers paradise where you can sit on the balcony with a glass of chilled wine and watch the dolphins play in the …see more

from $285 / night

$1995 - $2660 / week

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from $285 / night

(5) Excellent 

15

Anna Maria Island Vacation cottage rental

Florida / Anna Maria Island

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Shell Cottage is situated just 200ft away from the beautiful white sandy beach of Anna Maria which is 7 miles long. Set in a quiet leafy lane Shell shares our heated pool with our other 2 cottages and can be rented together or separately. Shell Cottage has a small sofa- …see more

from $135 / night

$945 - $1085 / week

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from $135 / night

(1) Good 

15

Vacation home in Anna Maria Island

Florida / Anna Maria Island

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
BEACHCOMBER, just 200ft from 7 miles of white sandy beach, is a beautifully furnished cottage with 2 bedrooms, 1 double and 1 twin. The master bedroom has an en-suite bathroom. There is also a 2nd bathroom with shower, WC and basin only. A large open plan living room …see more

from $145 / night

$1015 - $1225 / week

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from $145 / night

(33) Excellent 

42

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 enjoys a fantastic location 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) you could possibly need for a wonderfully relaxing holiday, ou …see more

from $172 / night

$1200 - $1800 / week

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from $172 / 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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avg. 1 hour 12 minutes

from $94 / 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 $108 / night

$752 - $1200 / week

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from $108 / night

(4) Very Good 

24

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Horizon West 112 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. Beach Bound.....This is your place!~ 2 bedroom 2 bath condo 1 very short block to beach. Beautifully decorated with comfortable furniture. Everything you need for a relaxing vacation. Pet fr …see more

from $115 / night

$731 - $1155 / week

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from $115 / night

(1) Excellent 

21

Home rental in Anna Maria

Anna Maria Island / Anna Maria

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This quiet, tre …see more

from $229 / night

$1600 - $2090 / week

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from $229 / night

33

Vacation home with shared pool in Anna Maria

Anna Maria Island / Anna Maria

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all …see more

from $465 / night

$3250 - $4015 / week

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from $465 / night

17

Home rental in Anna Maria

Anna Maria Island / Anna Maria

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll …see more

from $112 / night

$1400 - $1820 / week

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from $112 / 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. 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 bedrooms The master bedroom boast …see more

from $325 / night

$1400 - $2310 / week

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from $325 / night

(1) Very Good 

21

Vacation bungalow 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
This is a unique park on a beautiful barrier island, dating from 1940s with units ranging from vintage restored to luxurious manufactured homes. The park has a 55+ age requirement, no pets, and is perfectly landscaped and maintained. There is a clubhouse, library, boat …see more

from $79 / night

$495 - $700 / week

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avg. 2 hours 24 minutes

from $79 / night

(8) Excellent 

21

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

from $250 / night

$1250 - $1950 / week

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from $250 / night

(20) Very Good 

45

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of th …see more

from $290 / night

$1875 - $4750 / week

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avg. 2 hours 6 minutes

from $290 / night

(2) Excellent 

21

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge poo …see more

from $100 / night

$650 - $1400 / week

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from $100 / 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 $125 / night

$700 - $1200 / week

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from $125 / 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 $200 / night

$1125 - $1200 / week

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from $200 / night

24

Home rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Suitable for children age 5+
This rental home on Anna Maria Island sleeps up to 10 and comes fully equipped. This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderfu …see more

from $285 / night

$1995 - $4865 / week

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avg. 2 hours 36 minutes

from $285 / night

23

Vacation villa in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Lush tropical landscaped setting. Beautifully maintained two bedroom vacation rental on gorgeous Anna Maria Island. Secluded beaches, shopping, restaurants, golf, fishing and relaxation. Apartment includes full kitchen, 50' flat screen TV in living room, flat screen TV …see more

from $159 / night

$950 / week

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from $159 / night

(24) Excellent 

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

from $120 / night

$795 - $895 / week

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avg. 3 hours 47 minutes

from $120 / night

(5) Very Good 

21

Apartment rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
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 in Anna Maria Island, Florida. Ohana Hale Beachside is 150 feet to the white sand beaches and turquoise waters of the Gulf of Mex …see more

from $125 / night

$800 - $1150 / week

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avg. 1 hour 7 minutes

from $125 / night

(3) Excellent 

22

Bradenton Beach Vacation cottage rental

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Thank you for considering my home which has been recently updated to provide the warmth and feel of a true beach cottage. Wooden ceiling planks have been added along with pine beach chic cabinets and decor. I put many hours into the design of the home to provide a fee …see more

from $149 / night

$1043 / week

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Responds fast!
avg. 1 hour 40 minutes

from $149 / night

(9) Excellent 

14

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
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 in Anna Maria Island, Florida. Ohana Hale Beachside is 150 feet to the white sand beaches and turquoise waters of the Gulf of Mex …see more

from $135 / night

$851 - $1300 / week

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avg. 1 hour 7 minutes

from $135 / night

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
  • Air conditioning
  • Pet friendly
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 $150 / night

$2100 - $3500 / week

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avg. 3 hours 12 minutes

from $150 / night

(4) Very Good 

30

Vacation apartment with shared pool in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
Gulf Watch 111 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people. Peaceful Easy Island Living!~ Two bedrooms with en suite full baths this 2nd floor sun filled end unit condo is in the quiet Gulf Watch 32 unit complex with heated pool and s …see more

from $136 / night

$950 - $1375 / week

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from $136 / night

(12) Excellent 

23

Apartment rental 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
  • Air conditioning
Overlooking the Gulf of Mexico Beach, these 1250 square feet each two bedroom beach townhouses (complex of 4 apartments) arranged on two elevated levels offer beautiful views of Anna Maria island sound. A nice yard with a access to a barbecue area and a six persons tub …see more

from $220 / night

$1800 - $2450 / week

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avg. 1 hour 14 minutes

from $220 / night

(8) Excellent 

31

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This well-furnished two bedroom condo is next to a quiet nature preserve and has a fine view of the bay separating Anna Maria Island from Florida's mainland as well as the Sandy Pointe heated swimming pool. The beach is just 3 small blocks away with its bright white san …see more

from $125 / night

$720 / week

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from $125 / night

(1) Very Good 

15

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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

$1000 / week

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from $150 / night

31

Vacation villa in Anna Maria

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $145 / night

$845 - $1600 / week

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from $145 / night

(9) Very Good 

10

Bradenton Beach Vacation studio rental

Anna Maria Island / Bradenton Beach

Studio 5 2 nights min

  • Studio
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Watch the sunsets over the Gulf of Mexico from your private beachfront balcony. Beautifully decorated studio apartment sleeps four adults and 1 child. King size bed and a new full size Murphy bed accommodate the adults and a fold-a-bed from the ottoman will sleep a chil …see more

from $145 / night

$985 / week

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from $145 / night

(1) Excellent 

18

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
7901 Palm Dr- Duplex-2 bedroom 1 bath- Maximum Occupancy is 4 This is a very cute and well- appointed 2 bedroom 1 bath duplex. It has a Queen size bed in the master bedroom and a 2 twin size beds in the guest bedroom. It has a very nice comfortable sofa in the living …see more

from $135 / night

$900 - $1541 / week

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from $135 / night

(26) Excellent 

52

Vacation home rental

Anna Maria Island / Holmes Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $249 / night

$1494 / week

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avg. 1 hour 49 minutes

from $249 / night

(1) Excellent 

20

Vacation condo rental

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy paradise in this 2 bedroom, 2 bath suite. Newly renovated with all the amenities. The master suite features a king size bed with new dresser and night stands. The second bedroom has a queen bed with new dresser and night stands with large double closet. Each bathr …see more

from $118 / night

$825 - $1450 / week

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from $118 / night

(1) Very Good 

11

Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • 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 / week

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from $125 / night

(6) Excellent 

23

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make t …see more

from $269 / night

$1883 / week

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avg. 1 hour 4 minutes

from $269 / night

32

Vacation condo in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
We have just purchased this 2 bedroom 2 bath condo in August 2016 and just completed many improvements to make sure our guests are comfortable. We are offering a special rate of $650 per week* for stays through Dec 23, 2016 (so book now!) and have many available dates o …see more

from $100 / night

$700 - $1200 / week

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Responds fast!
avg. 2 hours 42 minutes

from $100 / night

21

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
  • Car not necessary
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 $200 / night

$1090 - $1696 / week

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Responds fast!
avg. 42 minutes

from $200 / night

24

Vacation apartment with shared pool in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
Gulf Watch 205 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people. Pristine Waters Await your Arrival!~ Gulf Watch Condo---2 bedroom, 2 bath condo in 32 unit complex with heated pool. Gulf to Bay setting. washer/dryer in unit. About 1200 squ …see more

from $136 / night

$950 - $1375 / week

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from $136 / night

31

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 2 Bedroom/ 3 Bath, maximum occupancy of 6 people. 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 Pointe on beautiful Anna Maria Island! Surroun …see more

from $122 / night

$851 - $1760 / week

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from $122 / night

1