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

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2,111 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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from $94 / night

(5) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $105 / night

$700 - $1,350 / week

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from $105 / 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 30 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
  • 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 30 minutes

from $130 / 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

(4) Excellent 

4

Vacation studio in Holmes Beach

Anna Maria Island / Holmes Beach

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • 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

$794 - $995 / week

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from $125 / 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

(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 30 minutes

from $200 / 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 - $1,350 / week

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avg. 3 hours 56 minutes

from $125 / 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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Responds fast!
avg. 1 hour 30 minutes

from $200 / 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. 2 hours 25 minutes

from $172 / night

(14) 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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avg. 3 hours 27 minutes

from $105 / 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. 34 minutes

from $235 / night

26

Vacation townhouse in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything! Salt Air West , located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island. Not in the mo …see more

from $149 / night

$999 - $2,499 / week

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from $149 / night

44

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Planning a fun family getaway or a trip with friends? Beach Retreat is the relaxing Anna Maria Island vacation rental just for you! The backyard's heated private pool is like a tropical oasis and this home's other top-notch amenities include a Ping-Pong table in the gar …see more

from $322 / night

$2,254 / week

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avg. 2 hours 25 minutes

from $322 / night

(1) Excellent 

34

Vacation apartment with shared pool in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
Harbor Lane Court Harmony - Condo 2 Bedroom / 2 Bath 2 blocks from the beach, maximum occupancy of 6 people. VRC16-000031 Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one two bedroom, 2 bath apartment. Just newly renovated, all uni …see more

from $144 / night

$900 - $1,600 / week

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from $144 / night

(6) Very Good 

24

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 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 30 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
  • 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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Responds fast!
avg. 1 hour 30 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 30 minutes

from $200 / night

30

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Ask about pets
The Terrace Condominium #2, located at 3100 Gulf Drive in Holmes Beach is a beautifully and comfortably furnished, two bedroom, two bath town home condo with heated pool, private garage and three separate lanais. The pool area is beautifully landscaped with native plant …see more

from $106 / night

$742 - $1,732 / week

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from $106 / 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
  • Child friendly
  • Car not necessary
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. 1 hour 30 minutes

from $130 / night

(1) Good 

12

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 30 minutes

from $130 / 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. 2 hours 25 minutes

from $122 / night

(3) Excellent 

15

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
  • Child friendly
  • Air conditioning
Come relax and enjoy your beach vacation at The Dolphin Club! 2 bedrooms and 1 bathroom, the master bedroom has a queen bed and the other has 2 twin beds. There is also a sleeper couch in the living room which can sleep 2 people. Fully air conditioned. Includes covered …see more

from $110 / night

$700 - $2,000 / week

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avg. 1 hour 36 minutes

from $110 / night

35

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
Make this Mediterranean-style home with a private lagoon-shaped pool, jetted tub, and easy beach access your home away from home when you come to Anna Maria Island. Come revel in luxury and local flavor! Located in the heart of Holmes Beach, yet tucked away from the hu …see more

from $136 / night

$952 / week

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avg. 2 hours 25 minutes

from $136 / night

20

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
The Siboney located at 3700 Gulf Drive in Holmes Beach, is an exquisite, executive level home with a private heated pool set amidst tropical, native landscaping. Its 2000 square feet of luxury! The beach is approximately one half block away with no major roads to cross. …see more

from $260 / night

$1,818 - $3,535 / week

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from $260 / 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 30 minutes

from $200 / night

19

Vacation apartment with shared pool in Holmes Beach

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 22 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. Community pool. VRC16-000068 If you're looking for total serenity and magnificent gulf front views then you've found the right place. This 2 bedroom/ 1 bath beachfront condo is …see more

from $158 / night

$1,100 - $2,000 / week

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from $158 / 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 30 minutes

from $156 / 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. 2 hours 25 minutes

from $115 / night

(5) Very Good 

23

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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 30 minutes

from $200 / 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. 2 hours 25 minutes

from $122 / night

(4) Very Good 

14

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fu …see more

from $300 / night

$2,100 / week

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from $300 / 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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Responds fast!
avg. 1 hour 30 minutes

from $150 / night

25

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
Explore Florida’s beautiful Anna Maria Island from ‘Salty Dogs Beach House,’ a 3-bedroom, 2.5-bathroom, single family Holmes Beach vacation rental house. With accommodations for 6, a gourmet kitchen, private backyard oasis and 2 decks overlooking the pool, this single u …see more

from $250 / night

$1,750 / week

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avg. 34 minutes

from $250 / 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

(14) Excellent 

28

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a …see more

from $158 / night

$1,100 - $1,650 / week

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avg. 3 hours 13 minutes

from $158 / 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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Responds fast!
avg. 1 hour 30 minutes

from $200 / night

(6) Excellent 

22

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 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

$885 - $1,390 / week

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Responds fast!
avg. 1 hour 30 minutes

from $165 / 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