
Pet-friendly holiday rentals in Summerland Key
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Summerland Key

Total holiday rentals
Explore 160 holiday rentals in Summerland Key

Nightly prices starting at
Summerland Key holiday rentals start at $118 NZD per night before taxes and fees

Verified guest reviews
Over 1,860 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
120 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
130 of Summerland Key holiday 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!
Top-rated pet-friendly home rentals in Summerland Key
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

2Bd/1Ba Waterfront Retreat w/35’ Dock
Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront modular home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, laundry in-house, nice wide canal with 35’ dock for your boat just steps from your door. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina w/marine fuel, wash station, store; tennis, bball, pickle ball, & playground. $125 add’l resort fee paid direct to Venture Out at gate. Incl Bikes & kayaks for use.
WalkabilityOutdoor spacesCondition

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!
Outdoor spacesWalkabilityIndoor spaces

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!
WalkabilityPetsIndoor spaces

Cottage
Experience island living at Sugarloaf RV Resort & Cottages in the Lower Keys, just 25 minutes from Key West. Our NEW Two-Bedroom Cottages sleep up to 6 guests with two queen beds and a full-size pull-out sofa. Enjoy a kitchenette with a double-burner stovetop, pots, pans, dorm fridge, microwave, K-Cup coffee maker, toaster, dishes, and utensils. Relax on your private patio and enjoy resort amenities including a heated / chilled pool, kayaks, paddle boards, bicycles, and a peaceful private lake.
PetsOutdoor spacesParks

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
Your Luxury Keys Getaway! Experience stunning Ocean views, amazing sunsets and sunrises, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Everything you need to fully enjoy the Keys experience! Keep your boat at the house and be on the Atlantic or Gulf in minutes. Located halfway between Key West and Marathon, you get access to all resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, book now!
PetsOutdoor spacesAccess

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!
Outdoor spacesPetsAccuracy

Starlight Serenity - Hideaway with Stunning Views
Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!
Outdoor spacesPetsSleep quality

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***
WalkabilityPetsView

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!
WalkabilityOutdoor spacesLayout

Oceanfront 2BR in Venture Out - 35’ Dock + Pool
Wake up to oceanfront sunrises in this 2BR/2BA coastal gem in Venture Out on Cudjoe Key. Enjoy turquoise water views, a 35’ seawall for boats up to 32’, and manatees gliding by. Fully equipped kitchen, private balconies, smart TVs, outdoor dining, grill, and more. Community perks include a heated pool, onsite store, tennis, pickleball and more. Just 20 mins to Key West! Pet friendly!. Gated entry, registration fee due at arrival.
WalkabilityHospitalityLocation

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.
WalkabilityOutdoor spacesAccess

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!
Outdoor spacesWalkabilityNearby
Popular amenities for Summerland Key pet-friendly home rentals
Pet-friendly house rentals

Blue Palms Retreat
Outdoor spacesAccessCleanliness

Oceanfront 360’ dock, tiki hut-dogs OK for a fee
WalkabilityOutdoor spacesBiking

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
CleanlinessLocationView

Soothing Nest
Outdoor spacesWalkabilityAmenities

Private Gated Cottage | Hot Tub | Pet Friendly
Outdoor spacesPetsNearby

Entire private two family water front home.
Outdoor spacesComfortBeach

Tropical Keys Retreat | Pool | Hot Tub | Cinema
PetsOutdoor spacesQuiet

Searenity Vacation Rental! Pool, Tiki Hut, Dockage
Outdoor spacesWalkabilityBathroom
Pet-friendly home rentals with a pool

Waterfront Condo Dock Pool Downtown Near Duval
WalkabilityPetsCleanliness

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
Outdoor spacesPetsParking

Oceanfront Bungalow Venture Out
Outdoor spacesAir conditioningLocation

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
WalkabilityPetsComfort

Ocean Front Home in Great Location
PetsOutdoor spacesQuiet

Villa Mars In Marathon
PetsOutdoor spacesCleanliness

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool
Outdoor spacesWalkabilitySleep quality

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor
Outdoor spacesAmenitiesWi-Fi
Private, pet-friendly home rentals

Tiny Home Aqua Lodges 2/1
WalkabilityPetsLocation

Blue Heaven Marathon
Outdoor spacesLocationHospitality

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club
PetsOutdoor spacesKitchen

SeaEsta! Bring your boat & 1 block to the beach!
WalkabilityOutdoor spacesNearby

Sombrero Sanctuary~ Pool, Pet Friendly, Near Beach
QuietAir conditioningIndoor spaces

Key West Outpost: eco-vacation
PetsOutdoor spacesSleep quality

Bayside Compound, Canal Dock, Pool, Bay Views
Outdoor spacesViewLocation

A Paradise Point by Sombrero Beach
PoolComfortKitchen
When is the best time to visit Summerland Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $517 NZD | $479 NZD | $533 NZD | $450 NZD | $453 NZD | $419 NZD | $396 NZD | $394 NZD | $365 NZD | $379 NZD | $399 NZD | $467 NZD |
| 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 |
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- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Conch Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Curry Hammock State Park
- Key West Aquarium





