50 Best Holmes Beach Vacation rentals on Holiday Lettings - House rentals

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468 Vacation rentals

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

(2) Excellent 

12

Holmes Beach Vacation villa rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a two bedroom one bath full size apartment. King bed in bedroom and …see more

from $140 / night

$835 - $1210 / week

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avg. 1 hour 25 minutes

from $140 / night

(20) 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 $215 / night

$1500 - $2250 / week

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from $215 / night

(3) Very Good 

45

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
SAVE $400.00 REGULAR SUMMER RATE FROM $2450.00 TO $2050.00 Adriel's Place in Anna Maria...located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted wit …see more

from $208 / night

$1450 - $2851 / week

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avg. 3 hours 26 minutes

from $208 / night

(27) 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 47 minutes

from $249 / night

(23) Very Good 

17

Vacation home rental

Anna Maria Island / Holmes 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. We …see more

from $125 / night

$850 - $1300 / week

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avg. 3 hours 11 minutes

from $125 / night

(2) Excellent 

22

Holmes Beach Vacation cottage rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool
ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your fa …see more

from $199 / night

$900 - $1300 / week

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avg. 1 hour 38 minutes

from $199 / night

(1) Excellent 

16

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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. 2 hours 18 minutes

from $130 / night

(2) Very Good 

14

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
  • Car not necessary
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 - $1350 / week

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avg. 2 hours 18 minutes

from $150 / night

(3) Excellent 

4

Vacation studio in Holmes Beach

Anna Maria Island / Holmes Beach

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
Located in the center of beautiful Anna Maria Island at the Manatee Public Beach. Castnetter 10 is a Pool - Side Studio with (1) full Bath, Queen size bed, and Queen size sleeper sofa. Refrigerator and microwave. …see more

from $125 / night

$875 / week

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from $125 / 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

(1) Excellent 

30

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Make your stay in Florida fun and easy! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up and down the coast. The condo is on the top floor (6th) of the building and is completely furnished with a dining table that seats 6 – 8, sofa and loveseat, …see more

from $295 / night

$2000 - $2100 / week

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from $295 / night

(3) Very Good 

21

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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

$1090 - $1750 / week

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avg. 2 hours 18 minutes

from $200 / night

30

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Tastefully decorated, two-bedroom, two-bath condo, located in Holmes Beach on quaint Anna Maria Island on the Gulf of Mexico. The condo complex has 32 units on one of Florida's finest beaches. You can walk the beach for miles in both a northerly and southerly direction. …see more

from $172 / night

$1200 / week

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from $172 / night

(4) 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

8

Vacation townhouse in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Sunset Inn in Holmes Beach is conveniently located on Gulf Drive. Close to shopping, dining, private and public beaches. Close to the free trolley stop that takes you anywhere on the island. Relax by the pool or take a short walk to the clear waters and white sand …see more

from $109 / night

$763 / week

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avg. 34 minutes

from $109 / night

(5) Excellent 

24

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
  • 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 $165 / night

$825 - $1390 / week

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avg. 2 hours 18 minutes

from $165 / night

(3) Excellent 

51

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf r …see more

from $408 / night

$2851 - $6600 / week

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from $408 / 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
  • Car not necessary
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 - $1350 / week

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avg. 2 hours 18 minutes

from $150 / 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

$1090 - $1750 / week

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Responds fast!
avg. 1 hour 25 minutes

from $200 / night

(2) Excellent 

20

Apartment rental 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 0.6 mi
  • Ask about children
Totally furnished apartment close to the beach. Spend quality time in a nice neighborhood. Enjoy activities such as playing tennis, kayaking, water skiing, fishing, painting, swimming, walking your dog and meeting new people at the dog park , the library or the Communit …see more

from $115 / night

$800 - $900 / week

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from $115 / night

(1) Very Good 

19

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
  • Car not necessary
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 - $1350 / week

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Responds fast!
avg. 2 hours 18 minutes

from $150 / 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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avg. 2 hours 18 minutes

from $130 / night

13

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Just a few steps to the beautiful powder-soft, white-sand Anna Maria Island Beach. This immaculate and inviting condominium is just one cottage away from being on the sand - but you save plenty! The large roof-top deck has a full, unobstructed gulf view, as shown in …see more

from $108 / night

$750 - $2800 / 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

$730 - $1155 / week

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from $115 / night

29

Vacation home rental

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
8201 Gulf Drive - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Welcome to 8201 Gulf Drive located on a spacious corner lot that is just a short stroll to the beach. Tastefully decorated, this beautiful residence was designed with you …see more

from $275 / night

$1800 - $2420 / week

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from $275 / night

(13) Excellent 

35

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
**Due to a house being built in frount of our building, we don't know how our views of the Mexican Gulf will be affected. We cannot guarantee that you will have the views depicted in our pictures.** 5 reasons why you will love our condos as much as we do: …see more

from $143 / night

$999 - $2150 / week

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avg. 11 minutes

from $143 / night

(2) Very Good 

10

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. Community pool. Escape to the Peaceful Shores of the Island!~ Island Beach Club--Gulf Front Condo---2 bedroom 1 bath ---10 unit building with solar heated shared pool. This c …see more

from $150 / night

$1050 - $2500 / week

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from $150 / night

14

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 0.1 mi
  • Child friendly
Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel applia …see more

from $150 / night

$852 - $2375 / week

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avg. 1 hour 32 minutes

from $150 / 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

(5) Very Good 

22

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
  • Car not necessary
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 - $1230 / week

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Responds fast!
avg. 1 hour 25 minutes

from $150 / 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 - $1695 / week

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avg. 2 hours 18 minutes

from $200 / night

(1) Excellent 

18

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This two bedroom, two-bath condo has been tastefully renovated and refurbished. The kitchen has new appliances and granite countertops. All the new furnishings make this a very comfortable home away from home. It has a private screened balcony off the living room and b …see more

from $130 / night

$900 / week

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from $130 / night

(2) Good 

31

Vacation apartment with shared pool in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Sandy Point 106 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. This comfortable 2 bedroom, 2 bath condo is in a great location; a quiet residential area yet within easy walking distance to the beach grocery, pharmacy and restaurants. In addition, there is …see more

from $135 / night

$700 - $1430 / week

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from $135 / night

(5) Very Good 

14

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
LaPlayita 5 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Unforgetable Vacations Created Here!~ Vaulted Ceiling in Living Room. Upper Level Master Bedroom/Bath. Lower Level Bedroom/Bath. Telephone, Cable TV, wi-fi internet service available. Fully Furnis …see more

from $115 / night

$800 - $1540 / week

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from $115 / night

171

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily with …see more

from $310 / night

$2170 - $4340 / week

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avg. 50 minutes

from $310 / night

36

Vacation home rental

Anna Maria Island / Holmes Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
You’ll be relaxing into that vacation frame of mind at first glimpse of this three story, key lime colored vacation home in the center of Holmes Beach. This luxury rental offers refreshing island luxury, an open floor plan with volume ceilings, a sprawling terrace, and …see more

from $240 / night

$1680 - $2800 / week

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avg. 50 minutes

from $240 / night

(5) Very Good 

17

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
  • Nearest beach 0.1 mi
  • Swimming pool
Come and put your toes in the sand! These large studios with a balcony sleep a maximum of 4 guests. This room has one King bed and 2 twin pull-outs, and are beautifully decorated. Relax on your private balcony and enjoy the breathtaking view of the sunsets and the beac …see more

from $109 / night

$750 - $1540 / week

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from $109 / night

22

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
4 Bedroom, 3 Bath - “Tina's Piece of Paradise” - 407 80th Street in Holmes Beach. When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Piece of Paradise”. After spending a week at this fabulous Holmes B …see more

from $265 / night

$1855 - $4025 / week

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avg. 1 hour 4 minutes

from $265 / night

(3) Very Good 

11

Holmes Beach Vacation villa rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a one bedroom one bath full size apartment. King bed in bedroom and …see more

from $120 / night

$725 - $1100 / week

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avg. 1 hour 25 minutes

from $120 / night