Pools and outdoor living are the centerpiece of a Florida beach vacation—your own private space to cool off, unwind after the sand, and stretch out like you’re at a resort (without sharing it).
SandboxBeachHouse.com keeps it relaxed and family-friendly with a private saltwater pool (pool heat is added to online bookings, $150 for a one-week stay), the outdoor bar pavilion and easygoing time in a fenced backyard. One dog up to 35 lb is welcome (pet fee applies).
Relax in a private saltwater pool steps from the Gulf in Holmes Beach on Anna Maria Island, with pool heat added to online bookings ($150 for one week). Family-friendly and dog-friendly (one dog up to 35 lb, with approval).
Read moreBook a private-pool beach house in Holmes Beach on Anna Maria Island. Family-friendly outdoor living and one dog up to 35 lb welcome with approval.
Read moreGet the best of both worlds: beach mornings and private pool afternoons on Anna Maria Island. Family-friendly and dog-friendly (one dog up to 35 lb, with approval).
Read moreSun loungers + a private pool make your Anna Maria Island stay feel resort-like—without the hotel crowds. One dog up to 35 lb welcome with approval.
Read moreEnjoy pool days and easy dinners with an outdoor grill at a relaxed, family-friendly Anna Maria Island rental. One dog up to 35 lb welcome with approval.
Read moreA private saltwater pool with a roofed outdoor bar pavilion beside it (bar stools, a serving bar, a beverage fridge/freezer) and mature trees around it, on Anna Maria Island. One dog up to 35 lb welcome with approval.
Read morePoolside outdoor dining makes your Anna Maria Island vacation feel resort-like—without shared hotel spaces. One dog up to 35 lb welcome with approval.
Read morePool safety tips for families staying at a private-pool rental on Anna Maria Island. No lifeguard, so an adult always watches. One dog up to 35 lb welcome with approval.
Read moreGet a resort-style backyard experience with a private saltwater pool on Anna Maria Island; online bookings add pool heat ($150 for one week). Relaxed, family-friendly, one dog up to 35 lb welcome with approval.
Read moreWalk back from the beach one house away, rinse off at the outdoor shower, then jump into your private saltwater pool. Family-friendly, one dog up to 35 lb welcome with approval.
Read moreEnjoy calm evening swims, the outdoor bar pavilion and outdoor Bose speakers at a private Holmes Beach rental on Anna Maria Island. Family-friendly, one dog up to 35 lb welcome with approval.
Read moreEnjoy a tropical, private pool setting on Anna Maria Island. Relaxed, family-friendly outdoor living with one dog up to 35 lb welcome with approval.
Read moreEnjoy a pool you never share, in a fenced tropical backyard in Holmes Beach on Anna Maria Island. Family-friendly and one dog up to 35 lb welcome with approval.
Read moreFind a private, uncrowded pool on Anna Maria Island—no hotel crowds, no shared pool. Family-friendly and one dog up to 35 lb welcome with approval.
Read moreStart your day with a morning swim in a private pool on Anna Maria Island; online bookings add pool heat ($150 for one week). Family-friendly and one dog up to 35 lb welcome with approval.
Read moreEnd the day with a sunset swim in a private pool on Anna Maria Island; online bookings add pool heat ($150 for one week). Family-friendly outdoor living with one dog up to 35 lb welcome with approval.
Read moreEnjoy a private saltwater pool, cleaned and treated by a pool service usually once a week, at a family-friendly Anna Maria Island rental. Relaxed outdoor living and one dog up to 35 lb welcome with approval.
Read moreFlorida showers happen—stay flexible with a private pool (online bookings add pool heat, $150 for one week) and comfortable outdoor living on Anna Maria Island. One dog up to 35 lb welcome with approval.
Read moreBuild your ideal day: beach mornings, pool afternoons, and a calm evening swim—then do it again tomorrow.
Island how-to
We could not confirm an island volleyball tournament, but there are courts: open-play sand volleyball at two county beach parks, and pickleball in Holmes Beach. Here is where to find a game and the rules that come with each place.