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Anna Maria Island & Holmes Beach Vacation Rentals with Private Pools

Browse professionally managed Anna Maria Island and Holmes Beach vacation rentals with a recorded fenced, unfenced or indoor private pool. Showing 49–72 of 1,169 matching vacation rentals, page 3 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Platinum Anna Maria Vacation Home Seven Bedroom
Anna Maria Island & Holmes Beach

Anna Maria Vacation Home Seven Bedroom

7 Bedrooms · 6 Bathrooms · Sleeps 8
From $3,257 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Gorgeous Home in Bradenton with Pool and Close to Beach
Anna Maria Island & Holmes Beach

Gorgeous Home in Bradenton with Pool and Close to Beach

7 Bedrooms · 7 Bathrooms · Sleeps 16
From $3,985 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Waterside Vacation Home One Block to The Beach
Anna Maria Island & Holmes Beach

Waterside Vacation Home One Block to The Beach

5 Bedrooms · 3 Bathrooms · Sleeps 14
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Luxury 4 Bedrooms, 5 Minute Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Luxury 4 Bedrooms, 5 Minute Walk to Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,209 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Vacation Home Roof Top Deck, Pool, Spa Steps to Beach
Anna Maria Island & Holmes Beach

Luxury Vacation Home Roof Top Deck, Pool, Spa Steps to Beach

5 Bedrooms · 4 Bathrooms · Sleeps 10
From $1,909 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Coastal Retreat in Holmes Beach Sleeps 8
Anna Maria Island & Holmes Beach

Luxury Coastal Retreat in Holmes Beach Sleeps 8

4 Bedrooms · 2 Bathrooms · Sleeps 8
From $739 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum An Island Paradise with Rooftop Views of Bay & Gulf
Anna Maria Island & Holmes Beach

An Island Paradise with Rooftop Views of Bay & Gulf

7 Bedrooms · 7 Bathrooms · Sleeps 17
From $2,093 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Holmes Beach Vacation Home Four Bedroom One Min Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home Four Bedroom One Min Walk to Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,014 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Bayfront Home at the North End of Anna Maria
Anna Maria Island & Holmes Beach

Luxury Bayfront Home at the North End of Anna Maria

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,658 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Water Views Anna Maria Island Vacation Home Four Bedrooms
Anna Maria Island & Holmes Beach

Water Views Anna Maria Island Vacation Home Four Bedrooms

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $3,889 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Bradenton Beach Vacation Pool Home Seven Bedroom
Anna Maria Island & Holmes Beach

Bradenton Beach Vacation Pool Home Seven Bedroom

7 Bedrooms · 7 Bathrooms · Sleeps 16
From $3,265 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Walk to Beach Holmes Beach Vacation Home With 4 Bedrooms
Anna Maria Island & Holmes Beach

Walk to Beach Holmes Beach Vacation Home With 4 Bedrooms

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,656 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria 4 Bedroom Vacation Villa with Private Pool
Anna Maria Island & Holmes Beach

Anna Maria 4 Bedroom Vacation Villa with Private Pool

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $2,210 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Island Vacation Home Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Walk to Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,209 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury 4-Bedroom Anna Maria Island Vacation Rental with Pool
Anna Maria Island & Holmes Beach

Luxury 4-Bedroom Anna Maria Island Vacation Rental with Pool

4 Bedrooms · 6 Bathrooms · Sleeps 8
From $2,536 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Nine Bedroom Luxury Vacation Villa in Bradenton Beach
Anna Maria Island & Holmes Beach

Nine Bedroom Luxury Vacation Villa in Bradenton Beach

9 Bedrooms · 9 Bathrooms · Sleeps 22
From $4,670 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Exquisite 4 Bedroom Vacation Rental with Great Amenities
Anna Maria Island & Holmes Beach

Exquisite 4 Bedroom Vacation Rental with Great Amenities

4 Bedrooms · 4 Bathrooms · Sleeps 10
From $3,376 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum New Luxury Beach House on Anna Maria Island Wow Factor
Anna Maria Island & Holmes Beach

New Luxury Beach House on Anna Maria Island Wow Factor

4 Bedrooms · 5 Bathrooms · Sleeps 8
From $4,653 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Luxurious Vacation Pool Home Close to Beach
Anna Maria Island & Holmes Beach

Anna Maria Luxurious Vacation Pool Home Close to Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $3,547 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Island & Holmes Beach Home 1011222
Anna Maria Island & Holmes Beach

Anna Maria Island & Holmes Beach Home 1011222

7 Bedrooms · 7 Bathrooms · Sleeps 16
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Gorgeous 4 Bedroom Pool Home in Anna Maria
Anna Maria Island & Holmes Beach

Gorgeous 4 Bedroom Pool Home in Anna Maria

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $3,878 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Island Beachfront Rental - Bradenton Beach Luxury Vacation Home
Anna Maria Island & Holmes Beach

Anna Maria Island Beachfront Rental - Bradenton Beach Luxury Vacation Home

5 Bedrooms · 5 Bathrooms · Sleeps 16
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Bay View & Steps to the Beach 6 Bedroom Vacation Home in Bradenton Beach
Anna Maria Island & Holmes Beach

Bay View & Steps to the Beach 6 Bedroom Vacation Home in Bradenton Beach

6 Bedrooms · 6 Bathrooms · Sleeps 14
From $3,988 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Gorgeous Brand New Build! Sleeps 18 Guests
Anna Maria Island & Holmes Beach

Gorgeous Brand New Build! Sleeps 18 Guests

8 Bedrooms · 8 Bathrooms · Sleeps 16
From $3,295 / night
Call to confirm availability941.500.4555 Request a callback & quote

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