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Anna Maria Cheap Rentals

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Bedrooms

Bathrooms

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5 mi
744 rentals in Anna Maria.
Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach, vacation rental in Anna Maria
Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach, vacation rental in Anna Maria
Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach, vacation rental in Anna Maria

Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming cottage in quiet area, close to beach & bay., vacation rental in Anna Maria
Charming cottage in quiet area, close to beach & bay., vacation rental in Anna Maria
Charming cottage in quiet area, close to beach & bay., vacation rental in Anna Maria

Charming cottage in quiet area, close to beach & bay.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Coral Cove: Walk to the Beach! Heated pool! Prime North End!, vacation rental in Anna Maria
Coral Cove: Walk to the Beach! Heated pool! Prime North End!, vacation rental in Anna Maria
Coral Cove: Walk to the Beach! Heated pool! Prime North End!, vacation rental in Anna Maria

Coral Cove: Walk to the Beach! Heated pool! Prime North End!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, vacation rental in Anna Maria
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, vacation rental in Anna Maria
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!, vacation rental in Anna Maria

Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stylish bayside condo with WiFi & pool - close to the beach & restaurants, vacation rental in Anna Maria
Stylish bayside condo with WiFi & pool - close to the beach & restaurants, vacation rental in Anna Maria
Stylish bayside condo with WiFi & pool - close to the beach & restaurants, vacation rental in Anna Maria

Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury home close to beach! Pool & putting green, vacation rental in Anna Maria
Luxury home close to beach! Pool & putting green, vacation rental in Anna Maria
Luxury home close to beach! Pool & putting green, vacation rental in Anna Maria

Luxury home close to beach! Pool & putting green

Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Castaway Cottage + Beach + Heated Private Pool & Spa = R & R!  Near Bean Point!, vacation rental in Anna Maria
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R!  Near Bean Point!, vacation rental in Anna Maria
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R!  Near Bean Point!, vacation rental in Anna Maria

Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay, vacation rental in Anna Maria
Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay, vacation rental in Anna Maria
Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay, vacation rental in Anna Maria

Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beachfront, EASTER SPECIAL, SEE RATES  Dogs R free, Walking Beach, Awesome views, vacation rental in Anna Maria
Beachfront, EASTER SPECIAL, SEE RATES  Dogs R free, Walking Beach, Awesome views, vacation rental in Anna Maria
Beachfront, EASTER SPECIAL, SEE RATES  Dogs R free, Walking Beach, Awesome views, vacation rental in Anna Maria

Beachfront, EASTER SPECIAL, SEE RATES Dogs R free, Walking Beach, Awesome views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kingfish- North end family home on canal!, vacation rental in Anna Maria
Kingfish- North end family home on canal!, vacation rental in Anna Maria
Kingfish- North end family home on canal!, vacation rental in Anna Maria

Kingfish- North end family home on canal!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cloud 9- beachfront/heated pool/ 4 plus bedroom, vacation rental in Anna Maria
Cloud 9- beachfront/heated pool/ 4 plus bedroom, vacation rental in Anna Maria
Cloud 9- beachfront/heated pool/ 4 plus bedroom, vacation rental in Anna Maria

Cloud 9- beachfront/heated pool/ 4 plus bedroom

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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SIRENIA COVE ~ Luxury Htd Pool, Waterfront, Dock, Ping Pong, Outdoor Bar/TV, vacation rental in Anna Maria
SIRENIA COVE ~ Luxury Htd Pool, Waterfront, Dock, Ping Pong, Outdoor Bar/TV, vacation rental in Anna Maria
SIRENIA COVE ~ Luxury Htd Pool, Waterfront, Dock, Ping Pong, Outdoor Bar/TV, vacation rental in Anna Maria

SIRENIA COVE ~ Luxury Htd Pool, Waterfront, Dock, Ping Pong, Outdoor Bar/TV

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay, vacation rental in Anna Maria
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay, vacation rental in Anna Maria
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay, vacation rental in Anna Maria

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serendipity Gulfront- gulf beach front, vacation rental in Anna Maria
Serendipity Gulfront- gulf beach front, vacation rental in Anna Maria
Serendipity Gulfront- gulf beach front, vacation rental in Anna Maria

Serendipity Gulfront- gulf beach front

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Northshore Beach House near Pine Ave, north end of Anna Maria Island, vacation rental in Anna Maria
Northshore Beach House near Pine Ave, north end of Anna Maria Island, vacation rental in Anna Maria
Northshore Beach House near Pine Ave, north end of Anna Maria Island, vacation rental in Anna Maria

Northshore Beach House near Pine Ave, north end of Anna Maria Island

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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AMI North End Private Heated Pool.  Great location to beach, vacation rental in Anna Maria
AMI North End Private Heated Pool.  Great location to beach, vacation rental in Anna Maria
AMI North End Private Heated Pool.  Great location to beach, vacation rental in Anna Maria

AMI North End Private Heated Pool. Great location to beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Breeze Cottages #1 (The Mahi-Mahi), vacation rental in Anna Maria
Bay Breeze Cottages #1 (The Mahi-Mahi), vacation rental in Anna Maria
Bay Breeze Cottages #1 (The Mahi-Mahi), vacation rental in Anna Maria

Bay Breeze Cottages #1 (The Mahi-Mahi)

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay, vacation rental in Anna Maria
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay, vacation rental in Anna Maria
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay, vacation rental in Anna Maria

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Anna Maria Island Rentals - Beach Front - "Angels Envy", vacation rental in Anna Maria
Anna Maria Island Rentals - Beach Front - "Angels Envy", vacation rental in Anna Maria
Anna Maria Island Rentals - Beach Front - "Angels Envy", vacation rental in Anna Maria

Anna Maria Island Rentals - Beach Front - "Angels Envy"

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury waterfront home with private pool, putting green, golf cart and bikes!, vacation rental in Anna Maria
Luxury waterfront home with private pool, putting green, golf cart and bikes!, vacation rental in Anna Maria
Luxury waterfront home with private pool, putting green, golf cart and bikes!, vacation rental in Anna Maria

Luxury waterfront home with private pool, putting green, golf cart and bikes!

Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Point's Hideaway - Beautiful Home w/Stunning Sunset/Water Views on Bean, vacation rental in Anna Maria
Point's Hideaway - Beautiful Home w/Stunning Sunset/Water Views on Bean, vacation rental in Anna Maria
Point's Hideaway - Beautiful Home w/Stunning Sunset/Water Views on Bean, vacation rental in Anna Maria

Point's Hideaway - Beautiful Home w/Stunning Sunset/Water Views on Bean

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Cottage on Pine - Luxury Boho Beach Cottage w/Pvt Heated Pool On Pine Ave!, vacation rental in Anna Maria
The Cottage on Pine - Luxury Boho Beach Cottage w/Pvt Heated Pool On Pine Ave!, vacation rental in Anna Maria
The Cottage on Pine - Luxury Boho Beach Cottage w/Pvt Heated Pool On Pine Ave!, vacation rental in Anna Maria

The Cottage on Pine - Luxury Boho Beach Cottage w/Pvt Heated Pool On Pine Ave!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Home with Pool, Outdoor Dining Area with BBQ - Whispering Whale Retreat, vacation rental in Anna Maria
Private Home with Pool, Outdoor Dining Area with BBQ - Whispering Whale Retreat, vacation rental in Anna Maria
Private Home with Pool, Outdoor Dining Area with BBQ - Whispering Whale Retreat, vacation rental in Anna Maria

Private Home with Pool, Outdoor Dining Area with BBQ - Whispering Whale Retreat

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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4.9 rated Island rental with exceptional testimonials for over 10 years!, vacation rental in Anna Maria
4.9 rated Island rental with exceptional testimonials for over 10 years!, vacation rental in Anna Maria
4.9 rated Island rental with exceptional testimonials for over 10 years!, vacation rental in Anna Maria

4.9 rated Island rental with exceptional testimonials for over 10 years!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Sirenia Beach House - Popular! - Waterfront/HotTub, vacation rental in Anna Maria
Sirenia Beach House - Popular! - Waterfront/HotTub, vacation rental in Anna Maria
Sirenia Beach House - Popular! - Waterfront/HotTub, vacation rental in Anna Maria

Sirenia Beach House - Popular! - Waterfront/HotTub

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa, vacation rental in Anna Maria
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa, vacation rental in Anna Maria
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa, vacation rental in Anna Maria

ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Coconut Lagoon - Lovely Historic Renovated Cottage w/Huge Heated Pool, vacation rental in Anna Maria
Coconut Lagoon - Lovely Historic Renovated Cottage w/Huge Heated Pool, vacation rental in Anna Maria
Coconut Lagoon - Lovely Historic Renovated Cottage w/Huge Heated Pool, vacation rental in Anna Maria

Coconut Lagoon - Lovely Historic Renovated Cottage w/Huge Heated Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!, vacation rental in Anna Maria
Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!, vacation rental in Anna Maria
Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!, vacation rental in Anna Maria

Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Gorgeous island luxury home just one block to the Beach! Come stay with us!, vacation rental in Anna Maria
Gorgeous island luxury home just one block to the Beach! Come stay with us!, vacation rental in Anna Maria
Gorgeous island luxury home just one block to the Beach! Come stay with us!, vacation rental in Anna Maria

Gorgeous island luxury home just one block to the Beach! Come stay with us!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Upscale waterfront home, private pool, beautiful views!, vacation rental in Anna Maria
Upscale waterfront home, private pool, beautiful views!, vacation rental in Anna Maria
Upscale waterfront home, private pool, beautiful views!, vacation rental in Anna Maria

Upscale waterfront home, private pool, beautiful views!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated Vintage AMI Cottage. Heated Pool! North End! 2 Blocks to Beach!, vacation rental in Anna Maria
Newly Renovated Vintage AMI Cottage. Heated Pool! North End! 2 Blocks to Beach!, vacation rental in Anna Maria
Newly Renovated Vintage AMI Cottage. Heated Pool! North End! 2 Blocks to Beach!, vacation rental in Anna Maria

Newly Renovated Vintage AMI Cottage. Heated Pool! North End! 2 Blocks to Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Anna Maria North End Retreat, Private Pool, 250 feet from the beach, vacation rental in Anna Maria
Anna Maria North End Retreat, Private Pool, 250 feet from the beach, vacation rental in Anna Maria
Anna Maria North End Retreat, Private Pool, 250 feet from the beach, vacation rental in Anna Maria

Anna Maria North End Retreat, Private Pool, 250 feet from the beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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MAGICAL NEST ON THE BEACH Heated pool & hot tub, 5 master suites DIRECT ON BEACH, vacation rental in Anna Maria
MAGICAL NEST ON THE BEACH Heated pool & hot tub, 5 master suites DIRECT ON BEACH, vacation rental in Anna Maria
MAGICAL NEST ON THE BEACH Heated pool & hot tub, 5 master suites DIRECT ON BEACH, vacation rental in Anna Maria

MAGICAL NEST ON THE BEACH Heated pool & hot tub, 5 master suites DIRECT ON BEACH

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Gone Coastal: *3 mins to beach *Pet-Friendly *Budget-friendly, vacation rental in Anna Maria
Gone Coastal: *3 mins to beach *Pet-Friendly *Budget-friendly, vacation rental in Anna Maria
Gone Coastal: *3 mins to beach *Pet-Friendly *Budget-friendly, vacation rental in Anna Maria

Gone Coastal: *3 mins to beach *Pet-Friendly *Budget-friendly

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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BON AMI: 3BR Family-Friendly Pool Home Less than Block from Beach, vacation rental in Anna Maria
BON AMI: 3BR Family-Friendly Pool Home Less than Block from Beach, vacation rental in Anna Maria
BON AMI: 3BR Family-Friendly Pool Home Less than Block from Beach, vacation rental in Anna Maria

BON AMI: 3BR Family-Friendly Pool Home Less than Block from Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anna Maria Beach Cottage 110B | Updated studio beach cottage, steps to the sand!, vacation rental in Anna Maria
Anna Maria Beach Cottage 110B | Updated studio beach cottage, steps to the sand!, vacation rental in Anna Maria
Anna Maria Beach Cottage 110B | Updated studio beach cottage, steps to the sand!, vacation rental in Anna Maria

Anna Maria Beach Cottage 110B | Updated studio beach cottage, steps to the sand!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Reef Romance managed by Beach Retreats, vacation rental in Anna Maria
Reef Romance managed by Beach Retreats, vacation rental in Anna Maria
Reef Romance managed by Beach Retreats, vacation rental in Anna Maria

Reef Romance managed by Beach Retreats

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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White Pearl-New Premier AMI Home with Sunset Views, vacation rental in Anna Maria
White Pearl-New Premier AMI Home with Sunset Views, vacation rental in Anna Maria
White Pearl-New Premier AMI Home with Sunset Views, vacation rental in Anna Maria

White Pearl-New Premier AMI Home with Sunset Views

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Sirenia By The Sea - 5/5 Popular! - Waterfront/Dock/Pool/ Hot Tub/Steps to, vacation rental in Anna Maria
Sirenia By The Sea - 5/5 Popular! - Waterfront/Dock/Pool/ Hot Tub/Steps to, vacation rental in Anna Maria
Sirenia By The Sea - 5/5 Popular! - Waterfront/Dock/Pool/ Hot Tub/Steps to, vacation rental in Anna Maria

Sirenia By The Sea - 5/5 Popular! - Waterfront/Dock/Pool/ Hot Tub/Steps to

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Tropical gem near beach with amazing Gulf view, pool, spa, game room & roof deck, vacation rental in Anna Maria
Tropical gem near beach with amazing Gulf view, pool, spa, game room & roof deck, vacation rental in Anna Maria
Tropical gem near beach with amazing Gulf view, pool, spa, game room & roof deck, vacation rental in Anna Maria

Tropical gem near beach with amazing Gulf view, pool, spa, game room & roof deck

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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**SPECIAL** Anna Cabana B: 1BR North End Pool Home, vacation rental in Anna Maria
**SPECIAL** Anna Cabana B: 1BR North End Pool Home, vacation rental in Anna Maria
**SPECIAL** Anna Cabana B: 1BR North End Pool Home, vacation rental in Anna Maria

**SPECIAL** Anna Cabana B: 1BR North End Pool Home

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beachview Retreat: Steps to the beach, Gulf views, hot tub!, vacation rental in Anna Maria
Beachview Retreat: Steps to the beach, Gulf views, hot tub!, vacation rental in Anna Maria
Beachview Retreat: Steps to the beach, Gulf views, hot tub!, vacation rental in Anna Maria

Beachview Retreat: Steps to the beach, Gulf views, hot tub!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Golf Cart, Bimini Cove by SeaBreeze Vacation, vacation rental in Anna Maria
Golf Cart, Bimini Cove by SeaBreeze Vacation, vacation rental in Anna Maria
Golf Cart, Bimini Cove by SeaBreeze Vacation, vacation rental in Anna Maria

Golf Cart, Bimini Cove by SeaBreeze Vacation

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Chillifish- Peaceful Floridian home., vacation rental in Anna Maria
Chillifish- Peaceful Floridian home., vacation rental in Anna Maria
Chillifish- Peaceful Floridian home., vacation rental in Anna Maria

Chillifish- Peaceful Floridian home.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique beach house near Bean Point, heated pool and just 3 min to beach., vacation rental in Anna Maria
Unique beach house near Bean Point, heated pool and just 3 min to beach., vacation rental in Anna Maria
Unique beach house near Bean Point, heated pool and just 3 min to beach., vacation rental in Anna Maria

Unique beach house near Bean Point, heated pool and just 3 min to beach.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Short stays available! 5-7 Minute Walk to the Gulf Beaches!, vacation rental in Anna Maria
Short stays available! 5-7 Minute Walk to the Gulf Beaches!, vacation rental in Anna Maria
Short stays available! 5-7 Minute Walk to the Gulf Beaches!, vacation rental in Anna Maria

Short stays available! 5-7 Minute Walk to the Gulf Beaches!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The TipSea Turtle managed by Beach Retreats, vacation rental in Anna Maria
The TipSea Turtle managed by Beach Retreats, vacation rental in Anna Maria
The TipSea Turtle managed by Beach Retreats, vacation rental in Anna Maria

The TipSea Turtle managed by Beach Retreats

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Mermaid Cove: Updated Forida Cottage w/pool, hot tub, vacation rental in Anna Maria
Mermaid Cove: Updated Forida Cottage w/pool, hot tub, vacation rental in Anna Maria
Mermaid Cove: Updated Forida Cottage w/pool, hot tub, vacation rental in Anna Maria

Mermaid Cove: Updated Forida Cottage w/pool, hot tub

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa, vacation rental in Anna Maria
Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa, vacation rental in Anna Maria
Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa, vacation rental in Anna Maria

Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria
Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria
Dragonfly - Southern charm on the North end of Anna Maria Island, vacation rental in Anna Maria

Dragonfly - Southern charm on the North end of Anna Maria Island

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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