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Serendipity Vacation Rentals

Serendipity Vacation Rentals

Member since 2023
16 rentals
598 reviews
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Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
63 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Steps to Beach + Heated Pool + Putting Green + Golf Cart | WavesWelcome to Waves, your beautifully remodeled coastal retreat on Anna Maria Island — where modern luxury, effortless beach access, and resort-style outdoor living create the ultimate island escape.Perfectly positioned just across...

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$966
avg per night
New
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Steps to Beach + Heated Pool + Golf Cart & Bikes | North End RetreatThis beautifully remodeled 4-bedroom, 4-bath Anna Maria Island vacation home is perfectly situated on the coveted north end — just steps from the Gulf of Mexico. With a convenient beach access path directly across the street,...

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$957
avg per night
New
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Salt + Sol | Canal-Front Oasis + NEW Heated Pool + Golf Cart | North End RetreatWelcome to Salt + Sol, your serene canal-front escape on the coveted north end of Anna Maria Island. This bright and breezy 4-bedroom home blends relaxed coastal elegance with modern comfort — all just minutes from...

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$671
avg per night
New
Anna Maria Island Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!Cottage 110A is a beautifully beachy place to call home on your next Anna Maria Island vacation! One of the charming Anna Maria Beach Cottages, this is a 2 bed/2 bath second-floor vacation home,...

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$450
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
58 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Waterfront Pool Retreat + Dock & Boat Lift + Golf Cart | Beach BlissWelcome to Beach Bliss, your waterfront escape on Anna Maria Island — where relaxed luxury, boating adventures, and effortless island living come together for an unforgettable stay.This beautifully designed 4-bedroom,...

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$959
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Limefish Luxury | Premier Gulf-Front Living & Iconic SunsetsTrue beachfront luxury with a private heated pool. Wake up to unobstructed Gulf views, step directly onto the sand, and enjoy total privacy in this stunning 3BR/3BA coastal retreat. Perfect for romantic escapes, work-from-the-beach stays,...

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$1,980
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Location, Location, LocationStaying near the Holmes Beach public beach means you get the best of the island without the hassle:Easy, stress-free beach access (no long walks or parking) Nearby public amenities like restrooms, showers & lifeguards Walk to restaurants, cafes & beach...

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$788
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Sandcastle – Beachside Escape with Heated Pool, Golf Cart & Island Adventure Gear3 Bedrooms | 2.5 Bathrooms | Heated Pool | Golf Cart | Bikes | Paddle Boards | Kayaks | Steps to the BeachWelcome to Sandcastle, your perfect Anna Maria Island beach retreat. Ideally located just across...

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$815
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
76 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Private Pool Oasis + Beach Volleyball Court + INCLUDED Golf Cart | Fanta-SeaEscape to Fanta-Sea, your private tropical retreat on the coveted north end of Anna Maria Island — where backyard fun, beachside relaxation, and effortless island exploring come together.Step through your back gate...

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$1,310
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
76 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | TripletailWelcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay.Perfectly...

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$1,473
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
34 reviews

Distance to beach: 50 feet to across the street

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Key Lime Cottage | Hot Tub + Fenced Yard + Golf Cart | North Shore Retreat 3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet Friendly | Private Hot Tub | 6-Passenger Golf CartWelcome to Key Lime Cottage, a charming north-end escape tucked along coveted North Shore Drive on Anna Maria Island. Just a short...

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$557
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
97 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

True Beachfront Escape + Elevator + Hot Tub + Golf Cart | Serendipity Anna MariaWelcome to Serendipity, your pet-friendly beachfront sanctuary on the coveted north end of Anna Maria Island — where quiet mornings, spectacular sunsets, and the rhythm of the Gulf create the perfect island escape.Perfectly...

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$1,111
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
69 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beachfront boho escape on Anna Maria Island NEW heated Gulfside pool + hot tub with sunset views 4BR layout with private cottage for extra space & privacy Steps to the sand + paddle boards, bikes & INCLUDED 6-passenger golf cart Serene north-end location — the island retreat guests...

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$1,351
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Shangri-La | Gated Bean Point Estate — Anna Maria Island’s Most Coveted LocationWelcome to Shangri-La, a rare and extraordinary beachfront estate perched on the exclusive tip of Anna Maria Island at Bean Point — widely considered the island’s most breathtaking and sought-after...

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$2,460
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms
39 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beachfront Luxury + Pool Deck + Complimentary Golf Cart | Cloud 9Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group...

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Featured review

"Paradise!"

This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!

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$2,148
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms
75 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Luxury Coastal Retreat + Elevator + Complimentary Golf Cart | Serendipity DeuxWhere luxury meets effortless island living, you’ll find Serendipity Deux — a beautifully designed 4-bedroom retreat offering refined interiors, premium beach access, and an unbeatable Anna Maria Island location.From...

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$2,075
avg per night
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