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Annapolis Holiday Rentals

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50 rentals in Annapolis.
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Modern, spacious home  w/ 2 gorgeous decks & shared pools/saunas - 2 dogs OK!, holiday rental in Annapolis

Modern, spacious home w/ 2 gorgeous decks & shared pools/saunas - 2 dogs OK!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub, holiday rental in Annapolis

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Oceanfront Home with Incredible Ocean Views, holiday rental in Annapolis

Stunning Oceanfront Home with Incredible Ocean Views

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub, holiday rental in Annapolis

Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Just Steps from the Ocean, holiday rental in Annapolis

Just Steps from the Ocean

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Come take in the ocean, gaze at the starry skies, commune with nature., holiday rental in Annapolis

Come take in the ocean, gaze at the starry skies, commune with nature.

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

Spacious Sea Ranch Home With Great Ocean Views

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Abalone Point:  Oceanside Panoramic View Home Near Shell Beach, holiday rental in Annapolis

Abalone Point: Oceanside Panoramic View Home Near Shell Beach

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Pipers Reach! Ocean view home, Steps to Shell beach and... dog friendly., holiday rental in Annapolis

Pipers Reach! Ocean view home, Steps to Shell beach and... dog friendly.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oceanview home w/ hot tub, patio & shared pool/tennis - 1/4 mile to the beach!, holiday rental in Annapolis

Oceanview home w/ hot tub, patio & shared pool/tennis - 1/4 mile to the beach!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Architectural gem w/ private hot tub, redwood views & shared pools - 1 dog OK!, holiday rental in Annapolis

Architectural gem w/ private hot tub, redwood views & shared pools - 1 dog OK!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanview & dog-friendly home w/ private hot tub plus pools & tennis access, holiday rental in Annapolis

Oceanview & dog-friendly home w/ private hot tub plus pools & tennis access

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront home w/ private hot tub & deck, beach access & shared pools/tennis!, holiday rental in Annapolis

Oceanfront home w/ private hot tub & deck, beach access & shared pools/tennis!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern oceanview home w/ private hot tub, near bluff trail w/ shared pools, more, holiday rental in Annapolis

Modern oceanview home w/ private hot tub, near bluff trail w/ shared pools, more

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic cabin w/ woodstove, deck with ocean views, and shared pools/tennis!, holiday rental in Annapolis

Historic cabin w/ woodstove, deck with ocean views, and shared pools/tennis!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dog-friendly, oceanview home with shared pool/ rec center access!, holiday rental in Annapolis

Dog-friendly, oceanview home with shared pool/ rec center access!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue water & white water views, private setting, shared pools, saunas & tennis!, holiday rental in Annapolis

Blue water & white water views, private setting, shared pools, saunas & tennis!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Holiday House: Peaceful, large Sea Ranch retreat, holiday rental in Annapolis

Holiday House: Peaceful, large Sea Ranch retreat

4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Stunning, upscale home w/ ocean views, hot tub & shared pool, tennis & sauna!, holiday rental in Annapolis

Stunning, upscale home w/ ocean views, hot tub & shared pool, tennis & sauna!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning oceanfront home on the bluffs w/ hot tub & shared pools/tennis!, holiday rental in Annapolis

Stunning oceanfront home on the bluffs w/ hot tub & shared pools/tennis!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning house w/ a private hot tub plus access to shared rec center pools, holiday rental in Annapolis

Stunning house w/ a private hot tub plus access to shared rec center pools

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dog-friendly cabin w/ocean view, private hot tub &  bbq, and access to pools!, holiday rental in Annapolis

Dog-friendly cabin w/ocean view, private hot tub & bbq, and access to pools!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous home w/ ocean views plus access to pools & tennis - walk to the beach!, holiday rental in Annapolis

Gorgeous home w/ ocean views plus access to pools & tennis - walk to the beach!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Meadow Getaway w/ Private Hot Tub, Walk to Shell Beach & Tide Pool Beach, holiday rental in Annapolis

Meadow Getaway w/ Private Hot Tub, Walk to Shell Beach & Tide Pool Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ocean view home w/ private hot tub, shared pools & beach access - dogs OK!, holiday rental in Annapolis

Ocean view home w/ private hot tub, shared pools & beach access - dogs OK!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ocean view home w/ private hot tub & shared pools/saunas!, holiday rental in Annapolis

Ocean view home w/ private hot tub & shared pools/saunas!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Secluded & newly remodeled luxurious home w/ forest view dining- Forest Getaway, holiday rental in Annapolis

Secluded & newly remodeled luxurious home w/ forest view dining- Forest Getaway

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern retro home w/ ocean views, a private hot tub, shared pool, & views, holiday rental in Annapolis

Modern retro home w/ ocean views, a private hot tub, shared pool, & views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sunny home w/ private hot tub & deck, shared pools & saunas - 2 dogs welcome!, holiday rental in Annapolis

Sunny home w/ private hot tub & deck, shared pools & saunas - 2 dogs welcome!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous oceanfront house w/private hot tub, shared tennis, pool, sauna & more!, holiday rental in Annapolis

Gorgeous oceanfront house w/private hot tub, shared tennis, pool, sauna & more!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Large oceanfront cottage with private hot tub, huge kitchen- Good for Groups!, holiday rental in Annapolis

Large oceanfront cottage with private hot tub, huge kitchen- Good for Groups!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Peaceful seaclusion with ocean view, patio, WiFi, Direct TV, 2 living rooms, holiday rental in Annapolis

Peaceful seaclusion with ocean view, patio, WiFi, Direct TV, 2 living rooms

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Oceanfront home w/ hot tub & shared pools/saunas - walk to beach, 2 dogs OK!, holiday rental in Annapolis

Oceanfront home w/ hot tub & shared pools/saunas - walk to beach, 2 dogs OK!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Large 3 story home with private hot tub & backyard- Ocean Pines Lodge, holiday rental in Annapolis

Large 3 story home with private hot tub & backyard- Ocean Pines Lodge

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Spacious Meadow Escape with Hot Tub, Deck, Ocean View & Fireplace- Viglione, holiday rental in Annapolis

Spacious Meadow Escape with Hot Tub, Deck, Ocean View & Fireplace- Viglione

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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180 Degree Panoramic Ocean View House on Meadow with WiFi, Private Balcony, holiday rental in Annapolis

180 Degree Panoramic Ocean View House on Meadow with WiFi, Private Balcony

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Whitewater ocean views w/ access to shared pools & tennis courts - dogs welcome!, holiday rental in Annapolis

Whitewater ocean views w/ access to shared pools & tennis courts - dogs welcome!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stylish House for Quiet Getaway, Ocean & Nature Views, Short Drive to Beaches, holiday rental in Annapolis

Stylish House for Quiet Getaway, Ocean & Nature Views, Short Drive to Beaches

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Custom-built woodland home w/ jetted tub, deck & shared pools/saunas!, holiday rental in Annapolis

Custom-built woodland home w/ jetted tub, deck & shared pools/saunas!

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Spacious multi-level house with high class kitchen & private hot tub, Stormfield, holiday rental in Annapolis

Spacious multi-level house with high class kitchen & private hot tub, Stormfield

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ocean view home w/ shared pools, tennis & saunas - 2 dogs OK!, holiday rental in Annapolis

Ocean view home w/ shared pools, tennis & saunas - 2 dogs OK!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pacific FantaSea House with Ocean View, Full Kitchen, Loft, holiday rental in Annapolis

Pacific FantaSea House with Ocean View, Full Kitchen, Loft

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pet friendly house w/ ocean views, board games, BBQ grill, 4 min to Shell Beach, holiday rental in Annapolis

Pet friendly house w/ ocean views, board games, BBQ grill, 4 min to Shell Beach

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bluff House with Hot Tub, Ocean View & Natural Light- WiFi included, holiday rental in Annapolis

Bluff House with Hot Tub, Ocean View & Natural Light- WiFi included

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spacious oceanfront getaway with Hot Tub, Garden, Apple TV, holiday rental in Annapolis

Spacious oceanfront getaway with Hot Tub, Garden, Apple TV

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean View Home w/ Fireplace & BBQ- Pacific Splendor, holiday rental in Annapolis

Ocean View Home w/ Fireplace & BBQ- Pacific Splendor

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private oceanfront, fireplace & hot tub, close to beach, Kaye Home (no wifi), holiday rental in Annapolis

Private oceanfront, fireplace & hot tub, close to beach, Kaye Home (no wifi)

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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New listing! Lovely home w/ a private hot tub, shared pool, & tennis - dogs OK!, holiday rental in Annapolis

New listing! Lovely home w/ a private hot tub, shared pool, & tennis - dogs OK!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Large, architect designed home with sea views on a private garden, pet friendly, holiday rental in Annapolis

Large, architect designed home with sea views on a private garden, pet friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sea Ranch Abalone Bay: Nature at Your Doorstep, holiday rental in Annapolis

Sea Ranch Abalone Bay: Nature at Your Doorstep

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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