
Pet-friendly vacation rentals in Summerland Key
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Summerland Key
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Cottage 30 min from Key West, free parking, pool
Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
The Snapper House is a spacious 3/2.5 bed/bath duplex with 45' of canal dock frontage, also Includes the Cabana Club with large pool (food/drinks for purchase) and ocean facing beach. Awning extends to dock from sliding doors. TV package includes 100+ channels Each bedroom and living room has a full size flat screen TV. For best WIFI reception, an extender is available and should be used when in the back bedrooms, it's name is the same as the main house with an "ext" at the end (same pw).

Island Paradise
*** Please note: There is a one time registration fee of $125 to be paid at gate*** Cozy keys getaway w/ ocean front heated pool, boat ramp and more. Relax in this 1 BR, 1 BA manufactured home in a resort style park with heated pool, hot tub, boat ramp, sports courts and walkable dining. This clean well kept home features a king bed in primary BR and queen gel memory foam pullout sofa in living room. Fully stocked kitchen! Hair dryer, shampoo, conditioner, bath soap, etc. are furnished.

Dolphin Daydreams at Venture Out
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** DOLPHIN DAYDREAMS is a freshly built 2-bedroom tropical home specifically designed to be the perfect antidote to the stresses of everyday life. Substitute zoom meetings and rush hour traffic for slow mornings on the patio and afternoons in the sun. Nestled within Venture Out, a popular resort community on Cudjoe

The Writer's Block- Key West
Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Waterfront Haven House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Florida Keys Resort-Style Home w/ Pool & Dock 5/3
Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!
Popular amenities for Summerland Key pet-friendly home rentals
Pet-friendly house rentals

Ocean Front Home in Great Location

Waterfront Oasis w/Private Pool-Dockage-Beach

Paradise Cove! 50ft Dock Pool BBQ

Sombrero Siesta Heated Pool & Stunning Canal Views

Paradise found

2BR/2BA Retreat in the heart of Marathon! 3 beds

Waterfront House with 37 ft Dock & Cabana Club

Water, Water Everywhere! "The Wheel House"
Pet-friendly home rentals with a pool

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Luxury Boating Paradise+Pool+Sailing Kayaks

Island Girl Big Pine Key

Golf Coast Oasis near Sombrero Beach

Private Pool! Luxury Paradise Pointe, Pet Friendly

Coral Lagoon* Winter specialrates*read description

Cielo's Del Mar 2 - Pool / Dock / Beach Luxury in KCB
Private, pet-friendly home rentals

Soothing Nest

Duval Corner - Pet friendly with Balcony

Waterfront Hideaway~ Canal Front Home, 24' Dock

Starlight Serenity - Hideaway with Stunning Views

Villa Mars In Marathon

Blue Ocean Bungalow-May dates now available

Waterfront FL Keys Cottage @ Venture Out

Turtle Cove
When is the best time to visit Summerland Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,050 | ﺩ.ﺇ988 | ﺩ.ﺇ870 | ﺩ.ﺇ848 | ﺩ.ﺇ848 | ﺩ.ﺇ859 | ﺩ.ﺇ856 | ﺩ.ﺇ793 | ﺩ.ﺇ867 | ﺩ.ﺇ801 | ﺩ.ﺇ922 |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about vacation rentals that are pet-friendly in Summerland Key

Total vacation rentals
Explore 150 vacation rentals in Summerland Key

Nightly prices starting at
Summerland Key vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 1,570 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
110 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
120 of Summerland Key vacation rentals include wi-fi access

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

4.8 Average rating
Summerland Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- Conch Key
- Bahia Honda State Park
- Long Beach
- Florida Keys Aquarium Encounters
- Sunset Park
- Dolphin Research Center
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Key West Lighthouse Museum
- Ernest Hemingway Home & Museum
- Robbies Marina Of Islamorada
- The Turtle Hospital
- Boyd's Key West Campground




