Annapolis Holiday Apartments
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5 km
50 rentals in Annapolis.
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 32 kms of Annapolis match all your filters:
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Just Steps from the Ocean
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious Sea Ranch Home With Great Ocean Views
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Dog-Friendly, Secluded Redwoods Getaway With Private Hot Tub
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dog-Friendly Home with WiFi, Ocean Views, Shared Pool, & Prime Location
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ARCHITECT-DESIGNED VIEW HOME AT THE SEA RANCH
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ocean View Home with Private Hot Tub, Trails Access, Shared Pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Great Escape | Luxe Sea Ranch home with hot tub, ocean view & yoga space
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Whitewater Ocean Views w/Access to Shared Pools & Tennis Courts – Dogs Welcome
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Retreat | Private Sanctuary
Holiday Rental House
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
Holiday Rental House
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
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Home w/Ocean View, Wood Burning Fireplace, Shared Pools & Tennis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sculpture Point (2-Bedroom Home) - Pets Allowed by RedAwning
Holiday Rental House
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
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Oceanfront Home with a Private Hot Tub, Bluff Views, & Shared Pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Meadow Cottage with Hot Tub, Gardens, Shared Pool, & Ocean Views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Viglione | Meadow Escape with Hot Tub
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Sea Garden (2-Bedroom Home) by RedAwning
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Binker Barn Reimagined
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Located on the hillside with a wonderful ocean view
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Tranquil, dog-friendly home w/ valley views and wood stove - close to trails
Holiday Rental House
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!
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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The Sonoma Treehouse (3-Bedroom Home) - Pets Allowed by RedAwning
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sweet Sea Ranch | Stylish House for Quiet Getaway, Short Drive to Beaches
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely home with water views, private setting, shared pools/saunas/tennis
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful, Ocean View Home with Courtyard, Gas Fireplace & Shared Pools/Saunas
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary coastal gem with ocean views, private hot tub, WiFi & more
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-Friendly Rustic Sea Ranch Home with Ocean View, Shared Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright Dog-Friendly Home Near Black Point Beach with Shared Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Seaclusion | Sea Views, Short Walk to Meadows and Bluff Trails
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Blue Sky Cottage- hillside, light- filled cottage.
Holiday Rental House
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!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Experience ocean front living at its finest!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dog-Friendly Oceanside Home with Classic Sea Ranch Architecture & Shared Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Seaward Bliss ★ (Private Hillside Retreat)
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Ocean Bluff Retreat with Private Hot Tub, Sauna, & Shared Pool
Holiday Rental House
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
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Hillside Vista with Dramatic Ocean Views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Pines Lodge | 3-Story Home w/ Private Hot Tub
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cloud 9 | Ocean views & new ownership!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dog-Friendly Oceanfront Home with Gorgeous Views, a Private Hot Tub & Shared
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Home with 2 Decks, Private Hot Tub - Shared Pools & Saunas
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront Home with Ocean Views, High-Speed WiFi, Gas Fireplace, & Washer/Dryer
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Home with Hot Tub, Deck, Shared Pool Access, & WiFi - Dogs OK
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Annapolis
- Yes, here are some popular holiday rentals in Annapolis that have a pool:
- Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
- Just Steps from the Ocean
- Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub
- Yes, here are some popular holiday rentals in Annapolis that have internet access:
- Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
- Just Steps from the Ocean
- Windsong...Oceanfront Views from ALL rooms, Single Story, & Private Hot Tub
- Some of the most popular kid friendly rentals in Annapolis are:
- Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
- Just Steps from the Ocean
- Spacious Sea Ranch Home With Great Ocean Views
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