Vacation Rentals with Pool in Eastham, MA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
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  4.  Massachusetts

  5.  Eastham

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66 Best Vacation Rentals with Pool in Eastham (Starting from $285)

Heated Saltwater Pool Hot Tub
Heated Saltwater Pool Hot Tub
House
Eastham, MA, USA
2.2k from Eastham center

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

4 Bedrooms8 Guests
New to Booking
$2170
Average price / night
Check Availability
Private Dog-Friendly Home with Heated Pool & Guest Cottage at National Seashore
Private Dog-Friendly Home with Heated Pool & Guest Cottage at National Seashore
House
Eastham, MA, 02642, United States
0.9k from Eastham center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$1076
Average price / night
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Beautiful Spacious Family Retreat w Pool
Beautiful Spacious Family Retreat w Pool
House
Eastham, MA, USA
2.6k from Eastham center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
9.7

Exceptional

3 reviews

$1540
Average price / night
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Cape Cod Oasis: Heated Salt Water Pool, Game Room, Bike Path!
Cape Cod Oasis: Heated Salt Water Pool, Game Room, Bike Path!
House
Eastham, MA, 02642, United States
1.0k from Eastham center

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

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$1038
Average price / night
Check Availability
Private pool 3 mins to Skaket Beach
Private pool 3 mins to Skaket Beach
House
Orleans, MA, USA
5.1k from Eastham center

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

4 Bedrooms10 Guests
New to Booking
$2494
Average price / night
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The Salt Pond House - Your Pool Escape By The National Seashore RPAM105
The Salt Pond House - Your Pool Escape By The National Seashore RPAM105
House
Eastham, MA, 02642, United States
1.3k from Eastham center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$933
Average price / night
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Stunning Home with In-Ground Pool
Stunning Home with In-Ground Pool
House
Orleans, MA, USA
5.4k from Eastham center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1642
Average price / night
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Pristine home w/heated saltwater pool, just minutes from beaches and bike trail.
Pristine home w/heated saltwater pool, just minutes from beaches and bike trail.
House
Eastham, MA, 02642, United States
1.5k from Eastham center

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

3 Bedrooms9 Guests
10.0

Exceptional

27 reviews

$1547
Average price / night
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Oasis near beach Pool large yard and airy kitchen
Oasis near beach Pool large yard and airy kitchen
House
Orleans, MA, USA
6.9k from Eastham center

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

4 Bedrooms8 Guests
New to Booking
$1304
Average price / night
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Lush gardens, in-ground pool, close to Coast Guard Beach
Lush gardens, in-ground pool, close to Coast Guard Beach
House
Eastham, MA, 02642, United States
2.0k from Eastham center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms10 Guests
New to Booking
$1433
Average price / night
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Self-Sufficient Cottages at Even'tide Resort
Self-Sufficient Cottages at Even'tide Resort
Resort
Eastham, Massachusetts, USA
7.3k from Eastham center

Cheap, Accommodations, Pools, Resorts, Parking, Lodgings, Places to stay, Family, Self-catering

18 Bedrooms38 Guests
9.0

Fabulous

3 reviews

$521
Average price / night
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New Eastham Oceanside Guest Suite with Pool and Hot Tub
New Eastham Oceanside Guest Suite with Pool and Hot Tub
Apartment
Eastham, MA, 02642, United States
2.2k from Eastham center

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

1 Bedroom2 Guests
10.0

Exceptional

15 reviews

$295
Average price / night
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The Villages at Ocean Edge Resort & Golf Club
The Villages at Ocean Edge Resort & Golf Club
Resort
MA, USA
9.1k from Eastham center

Accommodations, Pools, Resorts, Parking, Spa, Golf, Romantic, 3-star, Lodgings

247 Bedrooms51 Guests
8.5

Very Good

280 reviews

$364
Average price / night
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The Mansion at Ocean Edge Resort & Golf Club
The Mansion at Ocean Edge Resort & Golf Club
Resort
Brewster, MA, USA
9.2k from Eastham center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, 5-star, Lodgings, Beach

70 Bedrooms22 Guests
8.5

Very Good

80 reviews

$790
Average price / night
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Fabulous 6-bedroom 3 bath house w swimming pool, Pool House near 1st Encounter.
Fabulous 6-bedroom 3 bath house w swimming pool, Pool House near 1st Encounter.
House
Eastham, MA, 02642, United States
2.4k from Eastham center

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

6 Bedrooms12 Guests
New to Booking
$1585
Average price / night
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Private Pool and Close to Marconi Beach
Private Pool and Close to Marconi Beach
House
Wellfleet, MA, USA
9.3k from Eastham center

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

4 Bedrooms12 Guests
New to Booking
$1949
Average price / night
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Immaculately maintained, large beach home with heated swimming pool
Immaculately maintained, large beach home with heated swimming pool
House
Eastham, MA, 02642, United States
2.6k from Eastham center

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

5 Bedrooms10 Guests
9.6

Exceptional

28 reviews

$763
Average price / night
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Ocean Edge Retreat
Ocean Edge Retreat
Apartment
Brewster, MA, USA
9.9k from Eastham center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
6.6

Good

7 reviews

$285
Average price / night
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🐚The Bay Cottage on Thumpertown Beach
🐚The Bay Cottage on Thumpertown Beach
Cottage
Eastham, MA, 02642, United States
2.8k from Eastham center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.8

Exceptional

11 reviews

$379
Average price / night
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Luxury Cape Cod Compound-Heated Pool*Outdoor Kitchen*3 Connected Units (2302)
Luxury Cape Cod Compound-Heated Pool*Outdoor Kitchen*3 Connected Units (2302)
House
Eastham, MA, 02642, United States
3.1k from Eastham center

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

7 Bedrooms19 Guests
10.0

Exceptional

6 reviews

$1887
Average price / night
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White Crest: 009-O  Private Orleans resort with water views, heated pool/spa & fire pit
White Crest: 009-O Private Orleans resort with water views, heated pool/spa & fire pit
House
Orleans, MA, 02653, United States
3.4k from Eastham center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms14 Guests
10.0

Exceptional

11 reviews

$2016
Average price / night
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Hydrangea Hideaway: 236-O  Luxurious Orleans Estate w/Pool, Cabana, Game Room, and Stunning Finishes
Hydrangea Hideaway: 236-O Luxurious Orleans Estate w/Pool, Cabana, Game Room, and Stunning Finishes
House
Orleans, MA, 02653, United States
3.5k from Eastham center

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

6 Bedrooms14 Guests
New to Booking
$1562
Average price / night
Check Availability
 Luxury Waterfront Home with Pool and Dock  NEW 5% Discount Until Feb. 28th
Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th
House
eastham, MA, 02642, United States
3.7k from Eastham center

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

4 Bedrooms10 Guests
10.0

Exceptional

33 reviews

$1554
Average price / night
Check Availability
Pamet Lands Estate - Beautiful private Truro home with pool
Pamet Lands Estate - Beautiful private Truro home with pool
House
Eastham, MA, 02642, United States
3.8k from Eastham center

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

5 Bedrooms11 Guests
New to Booking
$840
Average price / night
Check Availability
Private estate, 3 homes, pool, outdoor kitchen, walk to beach!
Private estate, 3 homes, pool, outdoor kitchen, walk to beach!
House
Eastham, MA, 02642, United States
4.0k from Eastham center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

7 Bedrooms14 Guests
10.0

Exceptional

45 reviews

$2103
Average price / night
Check Availability
3 homes in one, pool, outdoor kitchen, wk to beach, great for multiple families
3 homes in one, pool, outdoor kitchen, wk to beach, great for multiple families
House
Eastham, MA, 02642, United States
4.1k from Eastham center

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

5 Bedrooms10 Guests
9.8

Exceptional

16 reviews

$1728
Average price / night
Check Availability
Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house
Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house
House
Orleans, MA, 02653, United States
4.1k from Eastham center

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

4 Bedrooms9 Guests
10.0

Exceptional

16 reviews

$1096
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 Eastham.

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Eastham Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 66 verified vacation rentals with a pool in Eastham. 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 Eastham vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $285 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Eastham 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 Eastham welcome pets. Currently, 19 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 Eastham 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 Eastham 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.