
Holiday rentals with outdoor seating in Osterville
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Osterville
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Cottage with private beach in Hyannis Port
Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Private Pool, near beaches, 3 BR/3 BA, Central Air
Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Cape Cod Beach House -Beach Pass Included!
Thoughtfully designed for travelers, by travelers, our relaxing beach bungalow is your perfect getaway! Relax & recharge while surrounded by gorgeous beaches with everything you need at your fingertips. Charming 2 bedroom home & peaceful yard within a quiet, centrally located neighborhood - hiking trails & beaches abound. Whether you’re staying for a weekend or a week, our comfortable home is the perfect spot for your Cape Cod getaway! Central Air, WiFi, Alexa & Beach Pass included too!

Upper Cape Cozy Cottage
Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

1-level fenced in yard Craigville Beach 2200sqft
Welcome to Midori On The Cape! This modern 4-bedroom, 2-bath, Cape-style house features ~2200 sq ft one-level Cape-style living in a quiet neighborhood, Free EV charging. 15000 sqft lot with fenced in flat grassy backyard, fire pit, swing set. Centrally located near Craigville Beach, Cape Cod Mall, vibrant Hyannis downtown and ferry terminal to Martha's Vineyard and Nantucket Island 1 living room, 2 dining areas, 4 super-sized bedrooms. Perfect for family staycation and gathering.

Cape Cod Getaway - 3BR/2BA Beach Pass Included
Spacious 3BR/2BA Cape Cod retreat on a quiet cul-de-sac in Barnstable. Perfect for families and groups, this home features a large deck with grill, Barnstable public Beach Pass (1 vehicle). Central A/C with 2 zones, Roku TVs in guest mode, fast Wi-Fi, and a fully equipped kitchen. Enjoy a kid-friendly basement with TV, plus full-size washer & dryer. Sleeps up to 8 with queen beds in every room. Ideal for a relaxing Cape Cod getaway, short drive to beaches, dining, and shops.

The Driftwood Home, 5 min from Mashpee Commons, AC
- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

Your dog will love it here and you will too.
If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Beachfront Cottage on White Pond (Marshmallow)
Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Relaxing Cottage in Centerville Village
Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with hammock. Just a short walk to the ocean, beaches, the library and the general store.

Wings Neck Lighthouse
Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

Cape Cod Cotuit Cottage, 3 Bed Near Beaches
5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!
Popular amenities for outdoor seating rentals in Osterville
House rentals with outdoor seating

Stunning Cape Home - Inground Pool, 5 Min To Beach

Three Ships Cove | Walk to Craigville Beach

Lake charm

Osterville- New Renovation, Central AC, Beach Pass

Spacious Modern Cottage, beach& Wychmere <1.4mile

Waterfront Spa|Hot Tub+Cold Plunge in Lake|King bd

★ Sunlit Escape: 200 Yards from the Beach!

Osterville 4BR, Hot Tub, Beach Pass, Walk to Pond
Apartment rentals with outdoor seating

Songbird Studio- Secluded but close to everything!

Cape Cod Beachfront 2 bedroom Cottage Harwich

Brand new! Whole apartment, huge tub, full kitchen

Spacious & bright, near beaches

Centerville Studio with Town Beach Pass

⭐ Gorgeous Beach Views -- The Sand Dollar Suite

Cozy Large Private Pet Friendly Studio

Apartment suite|Firepit|Private Deck|Pond Access
Apartment rentals with outdoor seating

Heart of downtown, walk to ferry, bikeway & beach!

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Hidden Hideaway

A Spectacular. Walk to beach, town and harbor 20

The Sea Salt Studio - Steps to the Beach!

Short walk to the Beach and Downtown Hyannis!

Lovely W Falmouth Home steps to bikeway & more!
When is the best time to visit Osterville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $325 SGD | $325 SGD | $358 SGD | $332 SGD | $456 SGD | $586 SGD | $651 SGD | $631 SGD | $467 SGD | $341 SGD | $391 SGD | $444 SGD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals with outdoor seating in Osterville

Total holiday rentals
Explore 90 holiday rentals in Osterville

Nightly prices starting at
Osterville holiday rentals start at $91 SGD per night before taxes and fees

Verified guest reviews
Over 2,570 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
90 of Osterville holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Osterville rentals

4.9 Average rating
Osterville stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Rentals with a fireplace Osterville
- Rentals with a firepit Osterville
- Rentals with a washing machine and dryer Osterville
- Family-friendly rentals Osterville
- Rentals with a patio Osterville
- Pet-friendly rentals Osterville
- House rentals Osterville
- Rentals with beach access Osterville
- Fitness-friendly rentals Osterville
- Rentals with pools Osterville
- Rentals with outdoor seating Barnstable
- Rentals with outdoor seating Barnstable County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Horseneck Beach State Reservation
- White Horse Beach
- Coast Guard Beach
- Second Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Island Park Beach
- The Breakers
- Minot Beach
- Nauset Beach
- Lighthouse Beach
- South Shore Beach
- Inman Road Beach
- Town Neck Beach
- Ellis Landing Beach
- Nickerson State Park