Vacation Rentals with Pool in Sea Street Beach, MA: Compare 10+ Sites & Save

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  Dennis Port
  6.  Sea Street Beach

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143 Best Vacation Rentals with Pool in Sea Street Beach (Starting from $183)

Pelham House Resort
Pelham House Resort
Resort
Dennis Port, MA, USA
0.1k from Sea Street Beach center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Beach, Places to stay

29 Bedrooms18 Guests
9.1

Superb

66 reviews

$756
Average price / night
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Charming 2-bedroom cottage in Dennis Port. 50 paces from the beach!
Charming 2-bedroom cottage in Dennis Port. 50 paces from the beach!
Cottage
Dennis, MA, 02639, United States
0.5k from Sea Street Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$377
Average price / night
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Bluegreen Dennis Port - The Soundings Seaside Resort - 2BD
Bluegreen Dennis Port - The Soundings Seaside Resort - 2BD
House
Dennis, MA, USA
0.7k from Sea Street Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms6 Guests
New to Booking
$590
Average price / night
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Only 1.5 hours to World Cup Boston Stadium & Steps to the Beach and Heated Pool!
Only 1.5 hours to World Cup Boston Stadium & Steps to the Beach and Heated Pool!
Apartment
Dennis, MA, 02639, United States
0.6k from Sea Street Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
9.8

Exceptional

6 reviews

$232
Average price / night
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The Three Seasons Resort
The Three Seasons Resort
Resort
Sea Street Beach, Dennis Port, Massachusetts, USA
0.7k from Sea Street Beach center

Accommodations, Pools, Resorts, Parking, Lodgings, Beach, Places to stay

12 Bedrooms15 Guests
7.8

Good

251 reviews

$510
Average price / night
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Skip to Beach, Cape Cod Condo!
Skip to Beach, Cape Cod Condo!
Apartment
Dennis, MA, 02639, United States
0.6k from Sea Street Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
8.8

Fabulous

3 reviews

$187
Average price / night
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Oceanside Condos
Oceanside Condos
Apartment
Sea Street Beach, Dennis Port, Massachusetts, USA
0.9k from Sea Street Beach center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach

40 Bedrooms20 Guests
8.4

Very Good

267 reviews

$275
Average price / night
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194 Captain Chase Road Dennis Port Cape Cod - - Beach Retreat I
194 Captain Chase Road Dennis Port Cape Cod - - Beach Retreat I
House
Dennis Port, MA, USA
0.9k from Sea Street Beach center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$205
Average price / night
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Sunny Rays: Where Poolside Bliss Meets Ocean Breeze!\"
Sunny Rays: Where Poolside Bliss Meets Ocean Breeze!\"
House
Dennis Port, MA, 02639, United States
0.8k from Sea Street Beach center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1636
Average price / night
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200 Captain Chase Road Dennis Port Cape Cod - - Beach Retreat II
200 Captain Chase Road Dennis Port Cape Cod - - Beach Retreat II
House
Dennis Port, MA, USA
1.0k from Sea Street Beach center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom2 Guests
9.0

Fabulous

3 reviews

$203
Average price / night
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3 BR, 2 1/2 BA. Across from beach. Heated outdoor pool  (pool closes Labor Day)
3 BR, 2 1/2 BA. Across from beach. Heated outdoor pool (pool closes Labor Day)
Condo
Dennis, MA, 02639, United States
0.9k from Sea Street Beach center

AC, Barbecue, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$739
Average price / night
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Bluegreen Dennis Port - The Soundings Seaside Resort - ST
Bluegreen Dennis Port - The Soundings Seaside Resort - ST
House
Dennis, MA, USA
1.2k from Sea Street Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
8.0

Good

1 reviews

$266
Average price / night
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Cozy Cape Cod Cottage - Private Pool & Beaches - Dennis Port, MA
Cozy Cape Cod Cottage - Private Pool & Beaches - Dennis Port, MA
Cottage
Dennis, MA, 02639, United States
1.0k from Sea Street Beach center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms4 Guests
New to Booking
$478
Average price / night
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Bluegreen Dennis Port - The Soundings Seaside Resort - 1BD
Bluegreen Dennis Port - The Soundings Seaside Resort - 1BD
House
Dennis, MA, USA
1.2k from Sea Street Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$396
Average price / night
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 Awesome Ocean Front Vacation Condo on the Cape in MA
Awesome Ocean Front Vacation Condo on the Cape in MA
Resort
Dennis, MA, 02639, United States
1.0k from Sea Street Beach center

AC, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
New to Booking
$183
Average price / night
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Bluegreen Vacations The Soundings, an Ascend Collection Resort
Bluegreen Vacations The Soundings, an Ascend Collection Resort
Resort
Sea Street Beach, Dennis Port, Massachusetts, USA
1.2k from Sea Street Beach center

Accommodations, Pools, Resorts, Parking, 4-star, Lodgings, Beach, Hot tubs, Places to stay

39 Bedrooms28 Guests
8.2

Very Good

94 reviews

$430
Average price / night
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Charming Studio less than 200 steps to Glendon Beach - 200 Captain Chase Rd #18
Charming Studio less than 200 steps to Glendon Beach - 200 Captain Chase Rd #18
Condo
Dennis, MA, 02639, United States
1.0k from Sea Street Beach center

AC, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

129 reviews

$233
Average price / night
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Edgewater Beach Resort
Edgewater Beach Resort
Resort
Sea Street Beach, Dennis Port, Massachusetts, USA
1.2k from Sea Street Beach center

Cheap, Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Beach, Hot tubs

76 Bedrooms12 Guests
9.1

Superb

118 reviews

$309
Average price / night
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Private Beach , in room Hot Tub, BBQ, HEATED POOL, INDOOR POOL
Private Beach , in room Hot Tub, BBQ, HEATED POOL, INDOOR POOL
Condo
Dennis, MA, 02639, United States
1.0k from Sea Street Beach center

AC, Barbecue, Free Parking, Hot Tub, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$343
Average price / night
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Luxurious Estate Private Heated pool
Luxurious Estate Private Heated pool
House
Harwich, MA, USA
1.9k from Sea Street Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

6 Bedrooms12 Guests
New to Booking
$3337
Average price / night
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56 Chase Ave - SD150
56 Chase Ave - SD150
Condo
Dennis Port, MA, 02639, United States
1.0k from Sea Street Beach center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
New to Booking
$352
Average price / night
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Sleeps 14 Home w Pool Great for Families
Sleeps 14 Home w Pool Great for Families
House
Harwich, MA, USA
2.2k from Sea Street Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

6 Bedrooms14 Guests
New to Booking
$1765
Average price / night
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A Beautiful Es-Cape
A Beautiful Es-Cape
Apartment
Dennis, MA, 02639, United States
1.1k from Sea Street Beach center

Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

1 Bedroom4 Guests
9.6

Exceptional

4 reviews

$228
Average price / night
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128 Lower County Road Dennis - The Moor-a-Sea
128 Lower County Road Dennis - The Moor-a-Sea
House
West Dennis, MA, USA
2.3k from Sea Street Beach center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$1512
Average price / night
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Charming Studio Dennis Port Getaway with WiFi and AC - Close to Beach!
Charming Studio Dennis Port Getaway with WiFi and AC - Close to Beach!
Condo
Dennis, MA, 02639, United States
1.1k from Sea Street Beach center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio, Pool, TV

1 Bedroom2 Guests
9.6

Exceptional

4 reviews

$234
Average price / night
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Relaxing condo near the beach with linens and towels provided!
Relaxing condo near the beach with linens and towels provided!
Condo
Dennis, MA, 02639, United States
1.1k from Sea Street Beach center

Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

5 reviews

$210
Average price / night
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The Soundings Seaside Resort, 2BR
The Soundings Seaside Resort, 2BR
Condo
Dennis, MA, 02639, United States
1.2k from Sea Street Beach center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
New to Booking
$379
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Sea Street Beach.

Where to stay in Sea Street Beach? Best neighborhoods & areas

Sea Street Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 143 verified vacation rentals with a pool in Sea Street Beach. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Sea Street Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $183 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Sea Street Beach offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Sea Street Beach welcome pets. Currently, 17 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Sea Street Beach often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Sea Street Beach offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.