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Annapolis Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Annapolis.
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach, vacation rental in Annapolis
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach, vacation rental in Annapolis
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach, vacation rental in Annapolis

Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Annapolis match all your filters:
Just Steps from the Ocean, vacation rental in Annapolis
Just Steps from the Ocean, vacation rental in Annapolis
Just Steps from the Ocean, vacation rental in Annapolis

Just Steps from the Ocean

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub, vacation rental in Annapolis
Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub, vacation rental in Annapolis
Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub, vacation rental in Annapolis

Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious Sea Ranch Home With Great Ocean Views, vacation rental in Annapolis
Spacious Sea Ranch Home With Great Ocean Views, vacation rental in Annapolis
Spacious Sea Ranch Home With Great Ocean Views, vacation rental in Annapolis

Spacious Sea Ranch Home With Great Ocean Views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub, vacation rental in Annapolis
Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub, vacation rental in Annapolis
Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub, vacation rental in Annapolis

Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location, vacation rental in Annapolis
Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location, vacation rental in Annapolis
Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location, vacation rental in Annapolis

Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ARCHITECT-DESIGNED VIEW HOME AT THE SEA RANCH, vacation rental in Annapolis
ARCHITECT-DESIGNED VIEW HOME AT THE SEA RANCH, vacation rental in Annapolis
ARCHITECT-DESIGNED VIEW HOME AT THE SEA RANCH, vacation rental in Annapolis

ARCHITECT-DESIGNED VIEW HOME AT THE SEA RANCH

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern Retro Home w/Ocean Views, Private Hot Tub, Shared Pool, & Views, vacation rental in Annapolis
Modern Retro Home w/Ocean Views, Private Hot Tub, Shared Pool, & Views, vacation rental in Annapolis
Modern Retro Home w/Ocean Views, Private Hot Tub, Shared Pool, & Views, vacation rental in Annapolis

Modern Retro Home w/Ocean Views, Private Hot Tub, Shared Pool, & Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Great Escape | Luxe Sea Ranch home with hot tub, ocean view & yoga space, vacation rental in Annapolis
The Great Escape | Luxe Sea Ranch home with hot tub, ocean view & yoga space, vacation rental in Annapolis
The Great Escape | Luxe Sea Ranch home with hot tub, ocean view & yoga space, vacation rental in Annapolis

The Great Escape | Luxe Sea Ranch home with hot tub, ocean view & yoga space

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front, Stunning Whitewater Views, Golf, Hike, Bike, vacation rental in Annapolis
Ocean Front, Stunning Whitewater Views, Golf, Hike, Bike, vacation rental in Annapolis
Ocean Front, Stunning Whitewater Views, Golf, Hike, Bike, vacation rental in Annapolis

Ocean Front, Stunning Whitewater Views, Golf, Hike, Bike

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Whitewater Ocean Views w/Access to Shared Pools & Tennis Courts – Dogs Welcome, vacation rental in Annapolis
Whitewater Ocean Views w/Access to Shared Pools & Tennis Courts – Dogs Welcome, vacation rental in Annapolis
Whitewater Ocean Views w/Access to Shared Pools & Tennis Courts – Dogs Welcome, vacation rental in Annapolis

Whitewater Ocean Views w/Access to Shared Pools & Tennis Courts – Dogs Welcome

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Retreat | Private Sanctuary, vacation rental in Annapolis
Ocean Retreat | Private Sanctuary, vacation rental in Annapolis
Ocean Retreat | Private Sanctuary, vacation rental in Annapolis

Ocean Retreat | Private Sanctuary

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Home with Ocean Views, Private Hot Tub, & Shared Pool - One Dog, vacation rental in Annapolis
Newly Renovated Home with Ocean Views, Private Hot Tub, & Shared Pool - One Dog, vacation rental in Annapolis
Newly Renovated Home with Ocean Views, Private Hot Tub, & Shared Pool - One Dog, vacation rental in Annapolis

Newly Renovated Home with Ocean Views, Private Hot Tub, & Shared Pool - One Dog

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean-View Home Near Pebble Beach with Private Hot Tub, Shared Pool, & WiFi, vacation rental in Annapolis
Ocean-View Home Near Pebble Beach with Private Hot Tub, Shared Pool, & WiFi, vacation rental in Annapolis
Ocean-View Home Near Pebble Beach with Private Hot Tub, Shared Pool, & WiFi, vacation rental in Annapolis

Ocean-View Home Near Pebble Beach with Private Hot Tub, Shared Pool, & WiFi

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Home w/Ocean View, Wood Burning Fireplace, Shared Pools & Tennis, vacation rental in Annapolis
Spacious Home w/Ocean View, Wood Burning Fireplace, Shared Pools & Tennis, vacation rental in Annapolis
Spacious Home w/Ocean View, Wood Burning Fireplace, Shared Pools & Tennis, vacation rental in Annapolis

Spacious Home w/Ocean View, Wood Burning Fireplace, Shared Pools & Tennis

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sculpture Point (2-Bedroom Home) - Pets Allowed by RedAwning, vacation rental in Annapolis
Sculpture Point (2-Bedroom Home) - Pets Allowed by RedAwning, vacation rental in Annapolis
Sculpture Point (2-Bedroom Home) - Pets Allowed by RedAwning, vacation rental in Annapolis

Sculpture Point (2-Bedroom Home) - Pets Allowed by RedAwning

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning house with water view, private hot tub, spacious deck & access to pools, vacation rental in Annapolis
Stunning house with water view, private hot tub, spacious deck & access to pools, vacation rental in Annapolis
Stunning house with water view, private hot tub, spacious deck & access to pools, vacation rental in Annapolis

Stunning house with water view, private hot tub, spacious deck & access to pools

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Oceanfront Home with a Private Hot Tub, Bluff Views, & Shared Pool, vacation rental in Annapolis
Beautiful Oceanfront Home with a Private Hot Tub, Bluff Views, & Shared Pool, vacation rental in Annapolis
Beautiful Oceanfront Home with a Private Hot Tub, Bluff Views, & Shared Pool, vacation rental in Annapolis

Beautiful Oceanfront Home with a Private Hot Tub, Bluff Views, & Shared Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Meadow Cottage with Hot Tub, Gardens, Shared Pool, & Ocean Views, vacation rental in Annapolis
Lovely Meadow Cottage with Hot Tub, Gardens, Shared Pool, & Ocean Views, vacation rental in Annapolis
Lovely Meadow Cottage with Hot Tub, Gardens, Shared Pool, & Ocean Views, vacation rental in Annapolis

Lovely Meadow Cottage with Hot Tub, Gardens, Shared Pool, & Ocean Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Viglione | Meadow Escape with Hot Tub, vacation rental in Annapolis
Viglione | Meadow Escape with Hot Tub, vacation rental in Annapolis
Viglione | Meadow Escape with Hot Tub, vacation rental in Annapolis

Viglione | Meadow Escape with Hot Tub

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Japanese-Inspired Retreat in the Redwoods w/ Fireplace & Wrap-Around Porch, vacation rental in Annapolis
Japanese-Inspired Retreat in the Redwoods w/ Fireplace & Wrap-Around Porch, vacation rental in Annapolis
Japanese-Inspired Retreat in the Redwoods w/ Fireplace & Wrap-Around Porch, vacation rental in Annapolis

Japanese-Inspired Retreat in the Redwoods w/ Fireplace & Wrap-Around Porch

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Custom-built woodland home with jetted tub, deck, & access to pools and saunas, vacation rental in Annapolis
Custom-built woodland home with jetted tub, deck, & access to pools and saunas, vacation rental in Annapolis
Custom-built woodland home with jetted tub, deck, & access to pools and saunas, vacation rental in Annapolis

Custom-built woodland home with jetted tub, deck, & access to pools and saunas

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Sea Garden (2-Bedroom Home) by RedAwning, vacation rental in Annapolis
Sea Garden (2-Bedroom Home) by RedAwning, vacation rental in Annapolis
Sea Garden (2-Bedroom Home) by RedAwning, vacation rental in Annapolis

Sea Garden (2-Bedroom Home) by RedAwning

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Moonraker (2-Bedroom Home) by RedAwning, vacation rental in Annapolis
Moonraker (2-Bedroom Home) by RedAwning, vacation rental in Annapolis
Moonraker (2-Bedroom Home) by RedAwning, vacation rental in Annapolis

Moonraker (2-Bedroom Home) by RedAwning

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Award-Winning Forest Getaway: *thesearanchhouse, vacation rental in Annapolis
Award-Winning Forest Getaway: *thesearanchhouse, vacation rental in Annapolis
Award-Winning Forest Getaway: *thesearanchhouse, vacation rental in Annapolis

Award-Winning Forest Getaway: *thesearanchhouse

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded hideaway charm near beach with wood-burning fireplace & wraparound deck, vacation rental in Annapolis
Secluded hideaway charm near beach with wood-burning fireplace & wraparound deck, vacation rental in Annapolis
Secluded hideaway charm near beach with wood-burning fireplace & wraparound deck, vacation rental in Annapolis

Secluded hideaway charm near beach with wood-burning fireplace & wraparound deck

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Located on the hillside with a wonderful ocean view, vacation rental in Annapolis
Located on the hillside with a wonderful ocean view, vacation rental in Annapolis
Located on the hillside with a wonderful ocean view, vacation rental in Annapolis

Located on the hillside with a wonderful ocean view

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tranquil, dog-friendly home w/ valley views and wood stove - close to trails, vacation rental in Annapolis
Tranquil, dog-friendly home w/ valley views and wood stove - close to trails, vacation rental in Annapolis
Tranquil, dog-friendly home w/ valley views and wood stove - close to trails, vacation rental in Annapolis

Tranquil, dog-friendly home w/ valley views and wood stove - close to trails

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern house w/ocean views, beautiful hiking trails, short walk to Pebble Beach!, vacation rental in Annapolis
Modern house w/ocean views, beautiful hiking trails, short walk to Pebble Beach!, vacation rental in Annapolis
Modern house w/ocean views, beautiful hiking trails, short walk to Pebble Beach!, vacation rental in Annapolis

Modern house w/ocean views, beautiful hiking trails, short walk to Pebble Beach!

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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The Sonoma Treehouse (3-Bedroom Home) - Pets Allowed by RedAwning, vacation rental in Annapolis
The Sonoma Treehouse (3-Bedroom Home) - Pets Allowed by RedAwning, vacation rental in Annapolis
The Sonoma Treehouse (3-Bedroom Home) - Pets Allowed by RedAwning, vacation rental in Annapolis

The Sonoma Treehouse (3-Bedroom Home) - Pets Allowed by RedAwning

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sweet Sea Ranch | Stylish House for Quiet Getaway, Short Drive to Beaches, vacation rental in Annapolis
Sweet Sea Ranch | Stylish House for Quiet Getaway, Short Drive to Beaches, vacation rental in Annapolis
Sweet Sea Ranch | Stylish House for Quiet Getaway, Short Drive to Beaches, vacation rental in Annapolis

Sweet Sea Ranch | Stylish House for Quiet Getaway, Short Drive to Beaches

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely home with water views, private setting, shared pools/saunas/tennis, vacation rental in Annapolis
Lovely home with water views, private setting, shared pools/saunas/tennis, vacation rental in Annapolis
Lovely home with water views, private setting, shared pools/saunas/tennis, vacation rental in Annapolis

Lovely home with water views, private setting, shared pools/saunas/tennis

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool, vacation rental in Annapolis
Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool, vacation rental in Annapolis
Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool, vacation rental in Annapolis

Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful, Ocean View Home with Courtyard, Gas Fireplace & Shared Pools/Saunas, vacation rental in Annapolis
Beautiful, Ocean View Home with Courtyard, Gas Fireplace & Shared Pools/Saunas, vacation rental in Annapolis
Beautiful, Ocean View Home with Courtyard, Gas Fireplace & Shared Pools/Saunas, vacation rental in Annapolis

Beautiful, Ocean View Home with Courtyard, Gas Fireplace & Shared Pools/Saunas

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary coastal gem with ocean views, private hot tub, WiFi & more, vacation rental in Annapolis
Contemporary coastal gem with ocean views, private hot tub, WiFi & more, vacation rental in Annapolis
Contemporary coastal gem with ocean views, private hot tub, WiFi & more, vacation rental in Annapolis

Contemporary coastal gem with ocean views, private hot tub, WiFi & more

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-Friendly Rustic Sea Ranch Home with Ocean View, Shared Pool, vacation rental in Annapolis
Dog-Friendly Rustic Sea Ranch Home with Ocean View, Shared Pool, vacation rental in Annapolis
Dog-Friendly Rustic Sea Ranch Home with Ocean View, Shared Pool, vacation rental in Annapolis

Dog-Friendly Rustic Sea Ranch Home with Ocean View, Shared Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright Dog-Friendly Home Near Black Point Beach with Shared Pool, vacation rental in Annapolis
Bright Dog-Friendly Home Near Black Point Beach with Shared Pool, vacation rental in Annapolis
Bright Dog-Friendly Home Near Black Point Beach with Shared Pool, vacation rental in Annapolis

Bright Dog-Friendly Home Near Black Point Beach with Shared Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Seaclusion | Sea Views, Short Walk to Meadows and Bluff Trails, vacation rental in Annapolis
Seaclusion | Sea Views, Short Walk to Meadows and Bluff Trails, vacation rental in Annapolis
Seaclusion | Sea Views, Short Walk to Meadows and Bluff Trails, vacation rental in Annapolis

Seaclusion | Sea Views, Short Walk to Meadows and Bluff Trails

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Blue Sky Cottage- hillside, light- filled cottage., vacation rental in Annapolis
Blue Sky Cottage- hillside, light- filled cottage., vacation rental in Annapolis
Blue Sky Cottage- hillside, light- filled cottage., vacation rental in Annapolis

Blue Sky Cottage- hillside, light- filled cottage.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely home w/ forest & partial ocean views, private hot tub, & high-speed WiFi!, vacation rental in Annapolis
Lovely home w/ forest & partial ocean views, private hot tub, & high-speed WiFi!, vacation rental in Annapolis
Lovely home w/ forest & partial ocean views, private hot tub, & high-speed WiFi!, vacation rental in Annapolis

Lovely home w/ forest & partial ocean views, private hot tub, & high-speed WiFi!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Experience ocean front living at its finest!, vacation rental in Annapolis
Experience ocean front living at its finest!, vacation rental in Annapolis
Experience ocean front living at its finest!, vacation rental in Annapolis

Experience ocean front living at its finest!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dog-Friendly Oceanside Home with Classic Sea Ranch Architecture & Shared Pool, vacation rental in Annapolis
Dog-Friendly Oceanside Home with Classic Sea Ranch Architecture & Shared Pool, vacation rental in Annapolis
Dog-Friendly Oceanside Home with Classic Sea Ranch Architecture & Shared Pool, vacation rental in Annapolis

Dog-Friendly Oceanside Home with Classic Sea Ranch Architecture & Shared Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Seaward Bliss ★ (Private Hillside Retreat), vacation rental in Annapolis
Seaward Bliss ★ (Private Hillside Retreat), vacation rental in Annapolis
Seaward Bliss ★ (Private Hillside Retreat), vacation rental in Annapolis

Seaward Bliss ★ (Private Hillside Retreat)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool, vacation rental in Annapolis
Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool, vacation rental in Annapolis
Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool, vacation rental in Annapolis

Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Forest House: 2  BR, 3  BA House in The Sea Ranch, Sleeps 4, vacation rental in Annapolis
Forest House: 2  BR, 3  BA House in The Sea Ranch, Sleeps 4, vacation rental in Annapolis
Forest House: 2  BR, 3  BA House in The Sea Ranch, Sleeps 4, vacation rental in Annapolis

Forest House: 2 BR, 3 BA House in The Sea Ranch, Sleeps 4

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Hillside Vista with Dramatic Ocean Views, vacation rental in Annapolis
Beautiful Hillside Vista with Dramatic Ocean Views, vacation rental in Annapolis
Beautiful Hillside Vista with Dramatic Ocean Views, vacation rental in Annapolis

Beautiful Hillside Vista with Dramatic Ocean Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Pines Lodge | 3-Story Home w/ Private Hot Tub, vacation rental in Annapolis
Ocean Pines Lodge | 3-Story Home w/ Private Hot Tub, vacation rental in Annapolis
Ocean Pines Lodge | 3-Story Home w/ Private Hot Tub, vacation rental in Annapolis

Ocean Pines Lodge | 3-Story Home w/ Private Hot Tub

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cloud 9 | Ocean views & new ownership!, vacation rental in Annapolis
Cloud 9 | Ocean views & new ownership!, vacation rental in Annapolis
Cloud 9 | Ocean views & new ownership!, vacation rental in Annapolis

Cloud 9 | Ocean views & new ownership!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Home with 2 Decks, Private Hot Tub - Shared Pools & Saunas, vacation rental in Annapolis
Spacious Home with 2 Decks, Private Hot Tub - Shared Pools & Saunas, vacation rental in Annapolis
Spacious Home with 2 Decks, Private Hot Tub - Shared Pools & Saunas, vacation rental in Annapolis

Spacious Home with 2 Decks, Private Hot Tub - Shared Pools & Saunas

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront Home with Hot Tub, Deck, Shared Pool Access, & WiFi - Dogs OK, vacation rental in Annapolis
Oceanfront Home with Hot Tub, Deck, Shared Pool Access, & WiFi - Dogs OK, vacation rental in Annapolis
Oceanfront Home with Hot Tub, Deck, Shared Pool Access, & WiFi - Dogs OK, vacation rental in Annapolis

Oceanfront Home with Hot Tub, Deck, Shared Pool Access, & WiFi - Dogs OK

Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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